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Holiday Rentals in Chicago, IL

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    All 195 Rentals in Chicago
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    Travellers to Chicago are booking July dates now. Secure your holiday home today, and have the perfect trip.
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    ₹11,488
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    1 / 12
    5 of 5 stars (1) Excellent
    Near North Side
    1 Bedroom / 1 Bathroom / Sleeps 4
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    ₹19,146
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    1 / 13
    5 of 5 stars (2) Excellent
    Near North Side
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    ₹8,616
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    5 of 5 stars (14) Excellent
    Southwest Side
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    ₹11,424
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    1 / 11
    5 of 5 stars (1) Excellent
    Roscoe Village
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Make our apartment the perfect home base for your family vacation or romantic getaway to Chicago. There is plenty of room to spread out and enjoy yourselves. The house is beautifully furnished and stocked with all of the essentials. The apartment is an easy walk to multiple bus and train lines,... View all property information
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    Location Information
    Chicago, Illinois 60618
    5 of 5 stars Reviewed 26 September 2014
    My wife and I travel to Chicago 4-6 times per year to visit our daughter and her family. We usually stay with her but this time she hosted her sister and their family which made...
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    ₹7,850
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    1 / 14
    4 of 5 stars (2) Very good
    3 Bedrooms / 1 Bathroom / Sleeps 8
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    • Air Conditioning
    • Dryer
    • Garden
    • Internet Access
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • ?
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    About this property
    Welcome! Welcome! Our single family brick house is located in a rare semi-private block about 5 miles West of Downtown. It has 3 Bedrooms, 1 Bathroom, Living Room, Dining Room and Full Kitchen. If you enjoy a quiet home with newer beds, clean sheets and towels, spaces, privacy, kitchen, laundry,... View all property information
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    Location Information
    Chicago, Illinois 60644
    5 of 5 stars Reviewed 19 July 2014
    Nice location. Everyone got their own beds. Easy to downtown. Kitchen and free laundry. Free Tide detergent too (not expected). Will stay again.
    3 of 5 stars Reviewed 8 May 2014
    The location of this property was great. It was about 12-15 minutes from downtown, which is where we wanted to be. There was plenty of on-street parking right in front of the...
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    ₹8,233
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    1 / 43
    Lakeview
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Located in Chicago's East Lakeview Neighborhood (home of Wrigleyville and Boystown), our Junior 1-Bedroom Apartment provides peace & quiet while only minutes away from Chicago's best attractions. Steps from Lake Michigan and Belmont Harbor; with easy access to the lakefront, nightlife, dining,... View all property information
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    Location Information
    Chicago, Illinois 60657
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    1 / 20
    4.5 of 5 stars (4) Very good
    1 Bedroom / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Plenty of free street parking is available on our block. This is the first floor of our home so we expect all guests to be QUIET & respectful. If you love to party, stomp around and yell then this is not the place for you. No parties, no loud music & no stumbling in drunk at 2 am. We are old &... View all property information
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    Location Information
    Chicago, Illinois 60609
    4 of 5 stars Reviewed 4 September 2014
    This was my first experience using Trip Advisor and renting a private home to stay in. The weekend was great. The apartment was located in a safe neighborhood to walk around in...
    5 of 5 stars Reviewed 12 November 2013
    From start to finish this rental was perfect. I was hesitant to rent from a private party, however great communication early on helped put me at ease. As a solo traveling female I...
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    ₹9,509
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    1 / 10
    4.5 of 5 stars (2) Very good
    3 Bedrooms / 1 Bathroom / Sleeps 8
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    • Air Conditioning
    • Dryer
    • Housekeeping...
    • Internet Access
    • Safe
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    This is a 3 Bed Room apartment of a two flat brick building in Andersonville area of Chicago. This apt has: 3 bedrooms, sleeps 8 Air Conditioners Free cell phone for international guests (plus deposit) Eat-in Kitchen Living Room Full size fridge Free parking Free laundry Complete kitchen Living... View all property information
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    Location Information
    Chicago, Illinois 60640
    4 of 5 stars Reviewed 11 July 2014
    I really enjoyed staying here. A great property. The sink did break while we were there but Jackie was right on getting it fixed for us! Great place, big enough for our group!
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    1 / 23
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    The South Loop is classic Chicago. In the South Loop, streets with decades of history come alive as music and life pulse magnetically. Chicago's South Loop is a neighborhood that's buzzing with bars, restaurants and entertainment; it's the perfect place to stay during your time in Chicago. The... View all property information
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    Location Information
    Chicago, Illinois 60616
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    ₹5,106
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    1 / 15
    4.5 of 5 stars (3) Very good
    Studio / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Dryer
    • Internet Access
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Furnished Studio. Double bed, full bath, and full kitchen. Unique location. You don't need a car living here. Plenty of transit options. A couple of blocks to Red line train station. Direct express bus to Chicago downtown stops right around the corner. 20 minutes to the city center by public... View all property information
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    Location Information
    Chicago, Illinois 60640
    4 of 5 stars Reviewed 4 September 2014
    Great stay, close to the El train and cheaper than a hotel! Able to stay parked out front for free and take the El where ever we wanted to. If you want a great stuffed pizza...
    5 of 5 stars Reviewed 8 July 2014
    the location of the apartment we stayed was convenient enough:only some min away from the red line train and a min from the bus stop,so getting to downtown is easy.we got a great...
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    ₹170,400
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    1 / 40
    4.5 of 5 stars (6) Very good
    The Loop
    Studio / 1 Bathroom / Sleeps 2
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Gym
    • Housekeeping...
    • Internet Access
    • Pool Table
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    About this property
    888.761.RENT or 312.242.1625 215 W. Washington St. Chicago, IL. 60606 (Washington/Wells in the Loop in Downtown Chicago - Five Blocks West of Michigan Avenue and Millenium Park 'Bean'; In Business/Theater District) Check Availability and Book Online Now: http://reservation.worldweb.com/hotel/1278... View all property information
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    Location Information
    Chicago, Illinois 60661
    5 of 5 stars Reviewed 19 July 2014
    Beautiful furnished apartments with kitchennete and in the heart of downtown, just a few blocks away from State st and michigan ave. I had a very pleasant and comfortable stay...
    5 of 5 stars Reviewed 8 May 2014
    The location is so convenient, the blue line train from O'hare airport takes you right to the stop of which is about 5 minutes walk to the building. The unit is clean and with...
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    ₹8,871
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    1 / 18
    4 of 5 stars (1) Very good
    The Loop
    Studio / 1 Bathroom / Sleeps 2
    travellers have booked this property
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    • Air Conditioning
    • Dishwasher
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Studio Apartment Downtown Chicago Millennium Park walking distance most attractions close to public transportation... View all property information
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    Location Information
    Chicago, Illinois 60602
    4 of 5 stars Reviewed 21 August 2014
    Tr`es bien situé, propre et bien équipé. Personnel de l'immeuble bien chaleureux. Pitsfield's café `a ne pas manqué au rez-de-chaussée. Calme , bien insonorisé...`a l'exeption de...
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    ₹16,529
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    1 / 37
    4 of 5 stars (5) Very good
    Near North Side
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    travellers have booked this property
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    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Studio Apartment Downtown Chicago Millennium Park walking distance most attractions close to public transportation... View all property information
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    Location Information
    Chicago, Illinois 60611
    4 of 5 stars Reviewed 19 August 2014
    Very strategic location near to major attractions. Very spacious and quiet. The best coffee is just down the building! The only thing was the wifi was extremely slow, me and my...
    3 of 5 stars Reviewed 1 July 2014
    security was not aware of our check in and had to call and verify. kitchen is not adequately stocked for those who may use knives, forks and wine glasses. it was, however...
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    ₹36,697
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    1 / 23
    5 of 5 stars (19) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 10
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Safe
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Spacious Bright Loft in the Heart of Everything Chicago 2 -10 adults, up to 12 with children Our funky warehouse & former tavern turned costume factory turned fabulous Lincoln Park home can be your home away from home in Chicago. Located in Chicago's newest neighborhood - 'SONO', at the... View all property information
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    Location Information
    Chicago, Illinois 60642
    5 of 5 stars Reviewed 27 May 2015
    Arrived after a long flight from UK, to find that the apartment was everything we had hoped for. Greeted by Carole who made us feel very welcome and gave us very useful local...
    5 of 5 stars Reviewed 20 April 2015
    Traveling to Chicago for a conference with 4 colleagues and rented the Magic Factory for a few nights in early April 2015. Booking was simple and Carole & Basil were great...
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    ₹229,753
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    1 / 22
    Near North Side
    Studio / 1 Bathroom / Sleeps 2
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    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Amazing unit features wall to wall cherry hardwood floors, stunning kitchen with quartz countertops and snaidero cabinetry, loads of storage space with professionally organized closets, floor to ceiling windows exposing great Chicago River and city skyline views, beautifully updated marble... View all property information
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    Location Information
    Chicago, Illinois 60601
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    ₹15,955
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    1 / 7
    4.5 of 5 stars (2) Very good
    Northwest Side
    2 Bedrooms / 2 Bathrooms / Sleeps 8
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Hot Tub
    • Internet Access
    • Safe
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Two bedrooms, two bathrooms condo apartment on the north side of Chicago. The apartment can accommodate 4 guests comfortably, but if need be can add two inflatable mattresses to accommodate up to 8 people. FREE Wireless internet access. FREE parking on public street in front of the building.... View all property information
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    Location Information
    Chicago, Illinois 60618
    4 of 5 stars Reviewed 31 March 2015
    Condo was clean and comfortable and looked recently updated. It was in a perfect location for us. Peter and Annie were very helpful and flexible in meeting our needs. Parking is...
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    1 / 14
    5 of 5 stars (9) Excellent
    Northwest Side
    Studio / 1 Bathroom / Sleeps 2
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The studio is situated in the couch house of the property. It is 300 square feet plus the bathroom. Beautiful decorated and very quiet place with the windows facing the beautiful garden. There is a washer and dryer on side and we can offer also breakfast. View all property information
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    Location Information
    Chicago, Illinois 60618
    5 of 5 stars Reviewed 20 September 2014
    The place is immaculate. Super clean and fully equipped. The location is great. You have the subway blue line (to downtown) in a short walk from the house to the station. The...
    5 of 5 stars Reviewed 1 September 2014
    I enjoyed my stay here and the hosts are warm, friendly and welcoming people. Hanne is just the sweetest person and I feel as if I have known her for many years. She always made...
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    ₹8,616
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    1 / 49
    5 of 5 stars (31) Excellent
    Southwest Side
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    We have two really incredible vacation rental apartments. The view in our first picture is our large hot tub. It's your new best friend after a day of travel, sightseeing, or business. The next photo is the amazing Chicago City Skyline view from our deck (closed in winter when there is snow... View all property information
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    Location Information
    Chicago, Illinois 60609
    4 of 5 stars Reviewed 1 June 2015
    We (two senior citizens, two adults and two children) enjoyed our stay at this apartment. Lots of space and totally equipped. It was great relaxing in the hot tub at the end of...
    5 of 5 stars Reviewed 13 November 2014
    Our family of four had an excellent time at this apartment. Bob was very easy to deal with and extremely helpful. Key code access to the apartment was very convenient. A garage...
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    ₹12,764
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    1 / 8
    4.5 of 5 stars (2) Very good
    Northwest Side
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This very affordable two bedroom, two bathroom apartment can sleep up to six guests. There are queen sized beds in each bedroom and a pull out couch in the living room. With features including: a breakfast table in the well-appointed kitchen; dining room; comfortable living room; a balcony;... View all property information
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    Location Information
    Chicago, Illinois 60630
    5 of 5 stars Reviewed 18 August 2014
    Nice apartment for up to 6 people, around $20 taxi ride from the Airport. Close to a large park, bus, and train stations. We purchased 7 days CTS passes for $33 each with...
    4 of 5 stars Reviewed 29 March 2014
    Bed was a little uncomfortable and broke often. Parking was difficult. Clean apartment, ideal for a large family
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    ₹204,225
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    1 / 15
    The Loop
    Studio / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Internet Access
    • Shared Indoor Pool
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Amazing unit features wall to wall espresso hardwood floors, stunning kitchen with quartz countertops and snaidero cabinetry, loads of storage space with professionally organized closets, floor to ceiling windows exposing great Chicago River and city skyline views, beautifully updated marble... View all property information
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    Location Information
    Chicago, Illinois 60601
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    ₹6,318
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    1 / 7
    5 of 5 stars (1) Excellent
    Northwest Side
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    If you are looking for a private, cozy, and comfortable place then this is just right for you. Here you can relax and lay back in a newly renovated unit with a private entrance for your convenience. Let the travel stress behind you and enjoy your stay in that great City we call HOME, Chicago We... View all property information
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    Location Information
    Chicago, Illinois 60618
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    ₹14,360
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    1 / 11
    4.5 of 5 stars (3) Very good
    Lakeview
    2 Bedrooms / 1 Bathroom / Sleeps 5
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Spacious, elegantly appointed and furnished Lakeview vacation/executive two bedroom, one bathroom apartment. First floor on a quiet tree-lined street, the entire apartment features; either oak floors or ceramic tiles, all solid oak doors and windows and oriental rugs. You will find our... View all property information
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    Location Information
    Chicago, Illinois 60657
    5 of 5 stars Reviewed 5 February 2015
    Good value for the money. We enjoyed the player piano. Beds were comfortable and everything was clean.
    4 of 5 stars Reviewed 29 July 2014
    Close to transit & grocery. Lots of space. Communication with Andy was great. He answered any questions we had before the trip in a timely manner. Easy check in and out...
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    ₹15,764
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    1 / 11
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    About this property
    TWO-BEDROOM SUITES WITH BALCONY Open gourmet kitchen with stainless appliances Granite breakfast bar Bright and sunny living room with 10' ceilings Private balcony complete with gas grill and patio furniture King-sized bed in the master bedroom Spa-like bathroom with glass shower Two Bedroom... View all property information
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    Location Information
    Chicago, Illinois 60640
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    ₹15,891
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    1 / 11
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    About this property
    Our suite features Two Bedrooms/Two Bathrooms with a pull out couch and can accommodate six guests. Suite also contains fully equipped gourmet kitchen and is perfect for families or individuals, traveling for business or pleasure. The Guesthouse Hotel offers great style, comfort and value. Stay... View all property information
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    Location Information
    Chicago, Illinois 60640
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    ₹274,427
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    1 / 37
    The Loop
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Huge beautiful 1 bedroom with loads of space and all furnishings you need. This unit features beautiful wall to wall hardwood floors and upgraded carpeting in bedroom, stunning updated kitchen with quartz countertops and espresso cabinetry, large marble bathrooms, floor to ceiling windows with... View all property information
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    Location Information
    Chicago, Illinois 60601
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    ₹11,169
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    1 / 7
    Near North Side
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    It is a great location in Downtown Chicago. It is close to everywhere. Opposite side is Northwestern Memorial Hospital , following building is Ann Lurie Children's Hospital. It is walking distance to Magnificent Mile (Michigan Ave.) , Navy Pier. There are restaurants , markets all around. Welcome... View all property information
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    Chicago, Illinois 60611
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    ₹12,700
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    1 / 17
    Northwest Side
    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Air Conditioning
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    • Sauna
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    • Pets allowed
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    • Suitable for children
    • ?
    • x
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    About this property
    Enjoy the entire house for a fraction of any hotel. Our house is a 10 room, 4 Bedroom, 3.5 Bathroom. Completely remodeled with huge fully equipped kitchen open to family room, perfect for entertaining, two story master suite with steam shower, double marble vanity, huge Jacuzzi, two walk in... View all property information
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    Chicago, Illinois 60659
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    1 / 13
    Northwest Side
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • x
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    About this property
    Two bedrooms, one bathroom condo apartment on the north side of Chicago. The apartment can accommodate 4 guests comfortably, but if need be can add two inflatable mattresses to accommodate up to 8 people. FREE Wireless internet access. FREE parking on public street in front of the building. Bus... View all property information
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    Location Information
    Chicago, Illinois 60618
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    ₹8,616
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    1 / 15
    Northwest Side
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Safe
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    • x
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    • x
    About this property
    Enjoy a great urban experience staying in the Ukrainian Village of Chicago! -- 2 bedroom flat perfect for short term stays. Convenient to shops, grocery, restaurants, library, bars, gym, swimming pool! THE SPACE: This main floor apartment includes the following amenities: Two comfortable bedrooms... View all property information
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    Location Information
    Chicago, Illinois 60622
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    1 / 23
    Near North Side
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Dryer
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
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    • Pets allowed
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    • ?
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    About this property
    Beautiful large true 1 bedroom space with plenty of square footage and stunning furnishings. Unit features wall to wall espresso hardwood floors, stunning kitchen with quartz countertops and snaidero cabinetry, loads of storage space with professionally organized closets, floor to ceiling windows... View all property information
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    Location Information
    Chicago, Illinois 60601
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    ₹12,700
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    1 / 16
    Roscoe Village
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Pets allowed
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    • x
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    • x
    About this property
    Welcome to your home away from home nestled in the Village within the City – Roscoe Village in Chicago, IL. Roscoe Village is a very family friendly neighborhood. This warm and welcoming first floor unit features a high end kitchen equipped with stainless appliances & granite countertops, 1 King... View all property information
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    Chicago, Illinois 60618
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    1 / 34
    Lincoln Square
    5 Bedrooms / 5 Bathrooms / Sleeps 12
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    • Hot Tub
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    • Pets allowed
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    • x
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    • x
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    About this property
    Huge 5 Bedroom-4.5 Bathroom home, 4 fire places, completely remodeled, fully furnished. Equipped kitchen with large breakfast island, separate dining room seating 8-10. Family room off the kitchen with fire place, huge deck and private back yard. Huge master bedroom with decorative fire place,... View all property information
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    Location Information
    Chicago, Illinois 60625
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    1 / 23
    Northwest Side
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Pets allowed
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    • x
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    About this property
    Live like a native in this artist-owned, artist-occupied vintage building located between the leading edge of the trendy Logan Square restaurant nexus and the old Polish neighborhood. Furnished in rustic Modern finds, it's on the Blue Line with easy access to the Loop and O'Hare. The unit has two... View all property information
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    Chicago, Illinois 60618
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    1 / 16
    2 Bedrooms / 1 Bathroom / Sleeps 3
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    • Air Conditioning
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    • Pets allowed
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    • x
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    • x
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    About this property
    Great 2b, 1 bath apartment in the walkable Ukrainian Village! Close to groceries, restaurants, shopping, clubs, public transportation, and easy access to downtown and the lake frowalk out of your apartment to the garden in the backyard, and enjoy your coffee, or watch the kids playing in the... View all property information
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    Location Information
    Chicago, Illinois 60622
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    1 / 55
    Northwest Side, Wicker Park / Bucktown
    3 Bedrooms / 5 Bathrooms / Sleeps 6
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    • Pets allowed
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    • Suitable for children
    • x
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    • x
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    About this property
    Architecturally significant single family home in Chicago's best neighborhood, Wicker Park. This home has been featured in design magazines and is ideal for entertaining. Filled with mid-mod furnishings throughout. Forbes rated Wicker Park #4 in the country for hippest neighborhoods, and this home... View all property information
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    Location Information
    Chicago, Illinois 60622
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    1 / 11
    The Loop
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Grill
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
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    • x
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    About this property
    Magnificent mile 1 brm convertible apt off Michigan Avenue in hotel district featuring 24 hr doorman, rooftop gym, sundeck, business ctr and garden patio. Your neighbors are the Hyatt, Fairmont and Radisson Blue. Gym, sundeck on rooftop 48th floor. Insane winter reductions!! North side prices in... View all property information
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    Location Information
    Chicago, Illinois 60601
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    ₹11,169
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    1 / 27
    4.5 of 5 stars (12) Very good
    3 Bedrooms / 1 Bathroom / Sleeps 5
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    • Air Conditioning
    • Balcony
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • x
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    About this property
    Located on the north side of the city near the lake, redline train, 15 minutes to downtown and northshore. Condo has central heat and air and offers 1200 square feet of living space with separate living room and dining room, your own balcony, and bedrooms with tasteful linens, ultra comfortable... View all property information
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    Location Information
    Chicago, Illinois 60660
    5 of 5 stars Reviewed 18 March 2015
    Our family planned a very last minute spring break trip to the Chicago area, and couldn't have been more pleased with our choice of rentals! The owners were very helpful and...
    5 of 5 stars Reviewed 17 April 2013
    We stayed for 6 days over Spring Break with our 14 year old. Loved that we had 2 bedrooms and kitchen/living/dining spaces....SO much better than the 3 of us crowded in a single...
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    5 of 5 stars (2) Excellent
    Lakeview
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
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    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
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    • Elder access
    • x
    About this property
    Our vintage apartment is located in the beautiful Chicago neighborhood of Lakeview with many ethnic restaurants and clubs with-in walking distance. Try a different ethnic specialty every night of the week. The apartment is in an ideal location to come and explore Chicago. Stroll 2 blocks through... View all property information
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    Location Information
    Chicago, Illinois 60657
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    1 / 28
    4 of 5 stars (5) Very good
    Rogers Park
    2 Bedrooms / 1 Bathroom / Sleeps 7
    travellers have booked this property
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    • Air Conditioning
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
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    • Elder access
    • x
    • ?
    About this property
    This listing is for a private 2-bedroom apartment in the Rogers Park neighborhood of Chicago. The apartment is over 1200 square feet (111 sq meters) and has tall 9.5' ceilings (2.9 meters), a marble bath, and hardwood floors throughout. There is also a charmingly retro yet fully functional kitchen... View all property information
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    Location Information
    Chicago, Illinois 60660
    5 of 5 stars Reviewed 2 January 2015
    Lisa and Caitlin did such an amazing job making the home comfortable and I loved the books about Chicago and the Book they had made with so much helpful information! The location...
    4 of 5 stars Reviewed 3 October 2014
    Three of us stayed at at Devon property and were thrilled with the accommodations. The location to the local bus and train stops were very convenient. The hosts, Lisa and...
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    ₹229,753
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    1 / 29
    Near North Side
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Dryer
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Beautifully updated studio unit features a large open layout with loads of closet space. Unit features wall to wall dark hardwood floors, updated upgraded kitchen with espresso cabinetry and beautiful granite countertops, large windows exposing beautiful skyline views, huge closet space, and w/d in... View all property information
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    Location Information
    Chicago, Illinois 60654
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    ₹5,425
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    5 of 5 stars (33) Excellent
    Northwest Side
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
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    • Elder access
    • x
    About this property
    A big thank you to my guests for their great reviews. I'm so honored to have earned a 2014 Certificate of Excellence from tripadvisor! Very comfortable, private lower level of duplex. Perfect for a business traveler who doesn't want to be downtown, or a couple visiting the city for pleasure.... View all property information
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    Location Information
    Chicago, Illinois 60625
    5 of 5 stars Reviewed 21 May 2015
    Cheryl made us feel like a guest in her home. She has a gift of hospitality that made our stay there welcoming and enjoyable. There is plenty of room and very clean and...
    4 of 5 stars Reviewed 11 December 2014
    Cheryl's apartment worked perfectly as a home base for my husband and me during a long weekend's visit to Chicago. We spent much of our time in and around the Loop, but found the...
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    4.5 of 5 stars (17) Very good
    West Town
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
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    • x
    • x
    About this property
    Situated on quiet side street across from 19c. church, steps from populars bars, restaurants, and public transportation. The apartment occupies the top two floors with large private roof top deck with magnificent views of Chicago skyline. First level contains large kitchen, living room/dining... View all property information
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    Location Information
    Chicago, Illinois 60642
    4 of 5 stars Reviewed 25 May 2015
    I came here for 5 days with a group of 7 (3 were couples, 1 was solo) This was place is a steal! it was wayyy bigger than we expected, we were all very comfortable, had our...
    5 of 5 stars Reviewed 19 March 2015
    The owners are super nice and answered all of my questions within a couple of days. The apartment has a lot of space to it. Three bathrooms makes it very comfortable. Two beds...
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    ₹22,209
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    1 / 18
    5 of 5 stars (2) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Want to live like a local while staying in Chicago and save? Reserve now and take advantage of fall savings! Our Chicago vacation rental offers an affordable and comfortable place to lay your head during your visit to our city! A family-owned, Chicago boutique property near Wrigley Field, The... View all property information
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    Location Information
    Chicago, Illinois 60640
    5 of 5 stars Reviewed 19 November 2014
    We came from a cold room in New York, an overpriced location...and I emailed the guesthouse , to warm up our appartment. What a surprise when we came in!! Everything so clean and...
    5 of 5 stars Reviewed 12 March 2013
    This property is everything the ad promises and more. From the luxurious appointments like the surround shower in the master suite to the fireplace and chef-quality kitchen, you...
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    1 / 10
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Live like a local and save! Book now to take advantage of discounted fall rates! Beautiful 2 Bedroom unit in boutique luxury building with 24 hour concierge service. Located in the wonderful and historic Andersonville neighborhood, The Guesthouse Chicago vacation rental encourages you to live... View all property information
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    Location Information
    Chicago, Illinois 60640
    5 of 5 stars Reviewed 19 May 2015
    Great property in Chicago, a short distance from Lakeshore Drive, perfect for a family vacation. We stayed in the spacious 2 bed/2 bath unit. The unit was stunning, with beautiful...
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    1 / 4
    The Loop
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Dryer
    • Internet Access
    • Shared Indoor Pool
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    A truly beautiful space that features a defined living area and bedroom space. Unit features wall to wall espresso hardwood floors, stunning kitchen with quartz countertops and snaidero cabinetry, loads of storage space with professionally organized closets, floor to ceiling windows exposing great... View all property information
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    Location Information
    Chicago, Illinois 60601
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    ₹12,062
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    1 / 16
    5 of 5 stars (37) Excellent
    3 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (37) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Fireplace
    • Internet Access
    • Safe
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    About this property
    City of Chicago Vacation LICENSE NO.: 2087699 This Vintage Early 1900’s 2-Flat 2nd floor apartment is in the beautiful tree-lined neighborhood of Andersonville. Located in the FUN, EXCITING, ECLECTIC ANDERSONVILLE Neighborhood on the north side of Chicago less than 2-blocks west of Clark Street... View all property information
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    Location Information
    Chicago, Illinois 60640
    5 of 5 stars Reviewed 8 May 2015
    Love Andersonville. Attractive, quiet & comfortable apartment with amenities and good parking options. Paul very responsive to any questions or concerns. Enjoyable stay. Hope to...
    5 of 5 stars Reviewed 31 March 2015
    This apartment was wonderful. It was clean and accessible to the trains. The parking was great. I was able to find street parking within 1/2 block at all times. The...
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    ₹6,382
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    2.5 of 5 stars (2) Poor
    Rogers Park
    3 Bedrooms / 1 Bathroom / Sleeps 8
    travellers have booked this property
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Perfect Home while visiting Chicago for a few days or longer stays, perfect for family gatherings, vacation, wedding stays, or simply enjoying time in The city. Walking distance to lots and public transportation! THE UNIT Lots of natural light due to the unit being on the top floor of nice and... View all property information
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    Location Information
    Chicago, Illinois 60626
    1 of 5 stars Reviewed 15 April 2015
    My sister was staying with us on (Apr.7) and opened the door and entered, NO HEAT,beds shabby very low to the floor and frumpy.The house was not up to advertised pictures on the...
    4 of 5 stars Reviewed 10 April 2015
    We like the house, it 's bright, lot of windows,it's a charming older home with hardwood floor.Very good location, walking distance to Loyola University and lake Michigan. There...
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    2 of 5 stars (1) Poor
    Rogers Park
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Dryer
    • Hot Tub
    • Internet Access
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    The Space Living room and dining room combo. Rooms are nice and cozy, cute and quiet. The unit is located in the East Rogers Park neighborhood of Chicago and border with Edgewater, within walking distance to the CTA Red Line Loyola station, Loyola University, restaurants, coffee shops, Lake... View all property information
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    Location Information
    Chicago, Illinois 60626
    2 of 5 stars Reviewed 6 May 2015
    Place was dark and damp. Bed sheets were clean, but pillows old and flat. Beds are double size. Towels were clean, but bathroom toilet area smelled moldy. Floors not very clean...
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    ₹9,573
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    1 / 14
    2 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Housekeeping...
    • Housekeeping...
    • Internet Access
    • Safe
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Modern 3BD 2Bth Brick-Style Ranch! Sleeps 10!! ASK ABOUT OUR PRICE MATCHING OPTION!! Very affordable home in west suburb that offers easy access to the city. Sleeps up to 10 people. -3 Bedrooms -2 Bathroom -Hardwood Floors -Tiled Bathroom -Centrally controlled Heat and Air -Big back yard... View all property information
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    Location Information
    Chicago, Illinois 60162
    From
    ₹204,225
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    1 / 23
    Near North Side
    Studio / 1 Bathroom / Sleeps 2
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    • Dryer
    • Internet Access
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Stunning Space Features wall to wall upgraded plush carpeting, beautiful open kitchen with granite countertops and stainless steel appliances, massive walk in closet with loads of storage space, floor to ceiling windows exposing eastern peak-a-boo lake views, beautifully updated bathroom, and w/d... View all property information
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    Location Information
    Chicago, Illinois 60611
    Chicago Holiday Rentals

    Located on the shores of Lake Michigan, Chicago is a stunning city bursting with attractions. Accommodation can be pricey, but choosing a rental property rather than a hotel is the ideal way to save money. Whether you prefer a spacious apartment in the city centre or a family house in a quieter area, you will feel relaxed and be able to organise your schedule as it suits you. You will of course find a host of restaurants catering to all tastes, but when you are tired of eating out, you can prepare your own food in a fully equipped kitchen.

    Chicago attractions

    You might not know where to begin seeing the sights of Chicago, so take a trolley tour to give you and your family an overview. A Wellenda Boat tour along the Chicago River and Lake Michigan is another wonderful way to see the city's architecture. Don't miss the Magnificent Mile, where the John Hancock Observatory offers spectacular views of the skyscrapers and Lake Michigan beyond. Art lovers should make a beeline for the Art Institute of Chicago, with its world-class collections of French and American Impressionists and Dutch Masters. The whole family will enjoy a visit to Millennium Park, where the star attractions are the Crown Fountain and the Chicago Bean, an enormous silver sculpture. You can try out the restaurant there, and you might be lucky enough to catch a music festival as well.

    Chicago holiday rentals for families

    Animal lovers must find time to visit Lincoln Park Zoo, where the Regenstein African Ape Centre, the Kovler Lion House and the Primate House will impress. The youngest members of the family will find the sea lions and penguins especially entertaining to watch. Before you leave Lincoln Park, children will love a visit to Adams Playground. If the weather calls for an indoor activity, head for Chicago Children's Museum at Navy Pier with its interactive exhibits. When you feel like a break from the city, spend some time on one of Lake Michigan's beaches, where you can swim, sunbathe, or go kayaking or canoeing.

    Budget holiday rentals in Chicago

    For a holiday in a vibrant city, Chicago is hard to beat. Hotels can be expensive, but renting your accommodation is the ideal low-cost alternative. Decide whether you would rather be in the city centre within walking distance of the attractions or in the quieter suburbs. Then have a look at our range of apartments and houses and choose the one that suits you best. It's worth reading through our unbiased customer reviews to help you. After that, you can look forward to what promises to be a holiday to remember in Chicago.