We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals in Chicago, IL

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    ₹ 0
    ₹ 11,558 Average
    ₹ 67,000+
    Bedrooms
    Any
    Amenities
    Any
    Neighbourhood
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travellers to Chicago are booking September dates now. Secure your holiday home today, and have the perfect trip.
    1 / 7
    5 of 5 stars (3) Excellent
    Northwest Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 7
    4 of 5 stars (9) Very good
    Lincoln Park
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 56
    4.5 of 5 stars (35) Very good
    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 21
    5 of 5 stars (3) Excellent
    Northwest Side
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    NO LARGE PARTIES!!!!great riverwest location in the heart of the city(1346 west augusta). 3 bed, 2 bath. 2800 square feet. 17 foot ceilings. perfect for entertaining. pool table, 115" movie theater,dart board, 2 blocks to bus/train line. you wont be disappointed. two bedrooms are located in the... View all property information
    Location Information
    Chicago, Illinois 60642
    5 of 5 stars Reviewed 7 June 2016
    The photos of this property do not quite do it justice. This property was everything and more than we had hoped for. This property is way bigger than it appears in the photos...
    5 of 5 stars Reviewed 23 March 2016
    Everything went excellent! Easy to get to resturants and bars. My friends and i were very impressed with the spacious home. It was clean and ready for entertaining. Pool table and...
    See all reviews
    1 / 13
    DePaul, Lincoln Park
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    PLEASE NOTE: This is not a new property. We have recently left our previous management company, which had been managing this and our other 6 properties for 2+ years. Please see photos for past reviews! Our historic Lincoln Park apartment features: 4 bedrooms and 2 baths Sleeping for 8 Premier... View all property information
    Location Information
    Chicago, Illinois 60614
    1 / 29
    5 of 5 stars (2) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Private Garden
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Waterfront
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    Andersonville, Edgewater, Loyola's campus and great restaurants, like Uncommon Ground, are a block away. Shopping and the lakefront are less than a 5 min walk away. There's no need for a car here, it's a short walk to the red line. The Space This is a large, bright, happy space. The apartment is... View all property information
    Location Information
    Chicago, Illinois 60660
    5 of 5 stars Reviewed 2 weeks ago
    I really enjoyed the condo with it stylish decor. John was so nice and accommodating. I needed a early check in and late check out and John accommodated both request. There was...
    5 of 5 stars Reviewed 18 June 2016
    This is a fabulous flat, exceptionally clean, comfortable, well equipped and well decorated! John is an extremely thoughtful host, providing fresh flowers in every room, fresh...
    See all reviews
    1 / 8
    West Town
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Indoor Pool
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    1 Bedroom, 1 Bathroom, Sleeps 2 We are the leading international provider of serviced apartment experiences. Whether you're staying three days, three weeks or three years we can give you the space, freedom and comfort of serviced apartment living. We offer luxury in Chicago's trendiest... View all property information
    Location Information
    Chicago, Illinois 60647
    1 / 8
    4 of 5 stars (3) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    LAST MINUTE CANCELLATION 60% OFF FOR THE WEEKEND OF THE AIR SHOW .One of three spacious apartments in a multi-flat historic building, located in the true artist oriented neighborhood in the heart of Chicago. Large kitchen space and a full newly remodeled bath with Jacuzzi tub and beautiful... View all property information
    Location Information
    Chicago, Illinois 60608
    5 of 5 stars Reviewed 13 July 2016
    Would reccomend! The apartment was much bigger than I had expected. The pictures did not do it justice. Amanda was a wonderful host. We had a great time!
    3 of 5 stars Reviewed 11 July 2016
    Owner seems new to visitor needs. Unit is really too small for 5 or 6 guests. Items that need to be addressed: 1). Let guests know they can request fresh bath towels. We had...
    See all reviews
    1 / 15
    Roscoe Village
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Porch
    • Outdoor Dining Area
    • Washer
    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Chicago, Illinois 60618
    1 / 16
    Near North Side
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    A rare opportunity to stay in Chicago's most prominent neighborhood! This fabulous apartment features 2 bedrooms and 1 bathroom, bright and spacious living room with a designated dining room. The kitchen comes fully equipped with dinnerware, flatware, pots and pans, french press coffee makers,... View all property information
    Location Information
    Chicago, Illinois 60610
    List your property for free!
    List your holiday home where TripAdvisor travellers can find it.
    Add a Listing
    1 / 10
    5 of 5 stars (3) Excellent
    Roscoe Village
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Washer
    • Satellite TV
    • Porch
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Chicago, Illinois 60618
    5 of 5 stars Reviewed 4 July 2016
    Very clean, modern, and responsive owner. It is located in a nice neighborhood that is close to public transportation.
    5 of 5 stars Reviewed 7 August 2015
    We needed a place to stay in Chicago close to family. This rental was perfect. There was more than enough room for 5 of us. It was extremely clean and very nicely decorated...
    See all reviews
    1 / 10
    5 of 5 stars (3) Excellent
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This 39-story Chicago hotel is across the river from Magnificent Mile shopping, six blocks from Lake Michigan, and a half-mile from the Loop's theater district and the Art Institute of Chicago. Located on the Magnificent Mile. Industry and creativity converge in Chicago, the birthplace of the... View all property information
    Location Information
    Chicago, Illinois 60601
    5 of 5 stars Reviewed 15 March 2016
    We recently stayed here for an extended weekend vacation and were very happy with this hotel. The location was perfect! Rooms were very spacious and clean! We even ordered...
    5 of 5 stars Reviewed 11 June 2015
    From the time that we checked in to the time that we left, everything was great. The staff and service was first rate. The rooms were clean and well kept. The front desk was very...
    See all reviews
    1 / 5
    West Town, Wicker Park / Bucktown
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Remember John Cusack's movie, High Fidelity? This would have been his dream Wicker Park apartment - right above Reckless Records, in the best part of the neighborhood - steps from the best bars, restaurants, shopping, the Blue Line el. Gorgeously appointed, a full European steam shower. This... View all property information
    Location Information
    Chicago, Illinois 60622
    1 / 7
    3.5 of 5 stars (2) Average
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Parking
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Last min cancellation trying get my renter some of her deposit back for her!In the heart of Pilsen in Chicago's Artist community. Beautiful city views. Unique space in Chicago's Historic district. One block from Thalia Hall. Fire Place, Brand new Bathroom/custom tile. Restored original Red hardwood... View all property information
    Location Information
    Chicago, Illinois 60608
    4 of 5 stars Reviewed 19 July 2016
    As long as you manage your expectations, this place is great! W It's in a rowhouse they are renovating in a Pilsen, a mostly hispanic area of town.The neighborhood is up and...
    3 of 5 stars Reviewed 1 June 2016
    The loft is decorated in a fun Moroccan theme. The building is nice and we found free street parking less than a block away. Walking distance to restaurants, bars and public...
    See all reviews
    1 / 15
    5 of 5 stars (2) Excellent
    Lakeview
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Washer
    • Waterfront
    • Patio
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Chicago, Illinois 60657
    1 / 21
    5 of 5 stars (1) Excellent
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Whether you are coming to stay at Raffaello Chicago for business, a romantic getaway, or traveling with your family and friends, we have the perfect accommodation ready and waiting for you.<BR><BR>Every Raffaello guest room reflects an upscale European style with soothing accents, subtle earth... View all property information
    Location Information
    Chicago, Illinois 60611
    5 of 5 stars Reviewed 27 February 2015
    We were lucky that we chose this place. It is in a perfectly managed hotel , Raffaello Hotel . Everything was ready to have a nice stay. Thanks
    See all reviews
    1 / 17
    Lakeview
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This unit is an officially licensed Chicago Vacation Rental. License #2438049 There’s nothing average about this 4-bedroom, 3-bath apartment in Lakeview. Whether it’s the vast interior with plenty of elbow room for 10 people, the premier location in one of Chicago’s most vibrant neighborhoods or... View all property information
    Location Information
    Chicago, Illinois 60613
    1 / 40
    5 of 5 stars (4) Excellent
    Lakeview
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • 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
    Location Information
    Chicago, Illinois 60657
    5 of 5 stars Reviewed 2 June 2016
    My wife and I are very happy with our stay. The studio is very tastefully decorated and many amenities provided. The location was perfect for our needs. We will definitely...
    5 of 5 stars Reviewed 7 April 2016
    I took my three little boys to Chicago for spring break. This location was perfect. About a five minute walk from the Belmont El station and lots of bus stops nearby. Many...
    See all reviews
    1 / 15
    4 Bedrooms, 1 Bathroom, Sleeps 17 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Room type: Entire home/apt Property type: Apartment Accomodate: 12+ Bedrooms: 3 Bathrooms: 1 Beds: 5 Check In: 3:00 PM Check Out: 12:00 PM Amenities Wifi Parking Kitchen utensils Price Extra People: $18 / night after the first guest . Cancellation level? Cleaning Fee: None Security Deposit:... View all property information
    Location Information
    Chicago, Illinois 60608
    1 / 19
    5 of 5 stars (1) Excellent
    Lakeview
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Porch
    • Wi-Fi
    • Patio
    • Satellite TV
    • DVD Player
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Chicago Guest House is the absolute BEST choice for business & leisure travelers who want to experience the sense of having arrived 'home' while they are in Chicago! A Vintage Beauty With All the Modern Comforts & Amenities. Beautifully furnished and fully equipped--guaranteed a unique and... View all property information
    Location Information
    Chicago, Illinois 60613
    5 of 5 stars Reviewed 29 April 2015
    I traveled to Chicago for a Baptism, meeting family from LA and Boston. We stayed in the Lakeview suite. Teri allowed us to enter the apt. early on the day of our arrival. The...
    See all reviews
    Get the List
    1 / 12
    5 of 5 stars (7) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Washer
    • Waterfront
    • DVD Player
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Elegant 1 bedroom apartment on N Lake Shore Drive,10 min away from Michigan Avenue, Northwestern Memorial Hospital, 25 min by bus to Millenium Park and the Art Institute. Fully furnished, 900 sq ft,beautiful oak floors, high ceilings, custom architectural details.Perfect residential accommodations... View all property information
    Location Information
    Chicago, Illinois 60613
    5 of 5 stars Reviewed 16 April 2012
    We were in Chicago to visit our daughter and this was our first stay at this 1 bedroom apartment. It was absolutely wonderful - cozy, well-appointed and suited our needs...
    5 of 5 stars Reviewed 9 December 2011
    My friend and I were blown away by this apartment, beautifully accomodation and accessible to the city with 3 regular buses passing by. The owner was very helpful and...
    See all reviews
    1 / 6
    Near South Side
    2 Bedrooms, 2 Bathrooms, Sleeps 3 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    A nice place to stay in the heart of Chicago. Beautiful home in a very convenient location. Lots of transportation, food, and entertainment, right at your fingertips. The home is also located within walking distance of McCormick Place, so if you're coming in town for a convention, this is place for... View all property information
    Location Information
    Chicago, Illinois 60616
    1 / 39
    4.5 of 5 stars (18) Very good
    Northwest Side
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Grill
    • Washer
    • DVD Player
    • Shared Garden
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • 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. We are city bee keepers as we learned they are very important for our... View all property information
    Location Information
    Chicago, Illinois 60618
    4 of 5 stars Reviewed 14 July 2016
    We loved staying here for our quick anniversary getaway! It was a short walk to the bus and train. We definitely would stay here again!
    4 of 5 stars Reviewed 13 July 2016
    Our stay at this rental was mostly pleasant. It's situated in the northern suburbs of Chicago. There were plenty of restaurants and stores in the neighborhood. Parking can be...
    See all reviews
    1 / 50
    5 of 5 stars (1) Excellent
    Lincoln Park
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Parking
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Fully furnished luxury apartment in the heart of Lincoln Park next to Oz Park. Walkscore 97/100. Brand new recently fully renovated 1 bedroom apartment, bathroom with jacuzzi tub, fireplace, hardwood floors, in unit laundry, private entrance and kitchen with new appliances. 700 square... View all property information
    Location Information
    Chicago, Illinois 60614
    5 of 5 stars Reviewed 8 July 2016
    I previously lived in Chicago for 5 years and chose this place based on the neighborhood. Not only is the Armitage and Halsted area the nicest part of Lincoln Park (with an 18...
    See all reviews
    1 / 16
    5 of 5 stars (1) Excellent
    Lincoln Park
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Patio
    • DVD Player
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Vacation in your own charming historic Lakeview / Lincoln Park 2-bdr & 2.5-bth Coach House with deck. Enjoy modern furnishings and amenities comfortably accommodating up to six guests. When you’re ready to explore the area, grab a bite to eat, drink, shop or play -- just a few steps out your door... View all property information
    Location Information
    Chicago, Illinois 60614
    1 / 11
    4.5 of 5 stars (2) Very good
    Northwest Side
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Patio
    • Porch
    • Balcony
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Hello and thank you viewing my condo's listing. My name is Bogdan and I am the property owner of this duplex. I'm a business professional and proud Chicagoan. If you are looking for comfortable, clean and modern accommodations, you've come to the right place. <BR><BR>My duplex is located in the... View all property information
    Location Information
    Chicago, Illinois 60647
    4 of 5 stars Reviewed 4 weeks ago
    This house in the Humboldt Park section of Chicago was a bargain. It's very spacious -- many bedrooms on 2 levels, sleeping about 10 people. LOADS of room. Never having visited...
    5 of 5 stars Reviewed 5 May 2016
    Such a fantastic space!! Originally we were to have 10 people in our group for the weekend, but after unexpected cancelations we were down to six or less. The space could easily...
    See all reviews
    1 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Grill
    • DVD Player
    • Shared Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to our modern, comfortable apt. We are conveniently located blocks from Pink Line train. We live in a fantastic neighborhood full of art, great food and many convenient grocery stores. 5 minutes from Rush Hospital on Pink line train. Our neighborhood has a family friendly vibe full of art... View all property information
    Location Information
    Chicago, Illinois 60608
    1 / 21
    4.5 of 5 stars (2) Very good
    Lakeview
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Patio
    • Grill
    • Air Conditioning
    • Washer
    • DVD Player
    • Satellite TV
    • Wi-Fi
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Chicago Guest House is the absolute BEST choice for business & leisure travelers who want to experience the sense of having arrived 'home' while they are in Chicago! Intimate & cozy and filled with character! Beautifully furnished and fully equipped--guaranteed a unique and unforgettable... View all property information
    Location Information
    Chicago, Illinois 60657
    5 of 5 stars Reviewed 11 September 2015
    Teri's Guest House at Newport is a wonderful home away from home for any type of traveler. Family getaway, girls/boys weekend, or a date weekend, this location and apartment meets...
    4 of 5 stars Reviewed 29 August 2015
    Great location!! Great neighbourhood!!! The red line is within walking distance. Just be prepared for massive crowds after a baseball game. Walking distance to the grocery...
    See all reviews
    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Satellite TV
    • Grill
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Chicago, Illinois 60640
    1 / 10
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • DVD Player
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    - The Space::: Spacious Convertible Studio that will comfortably accommodate 4 but can sleep 5 adults with a Queen Size private bed and a full size convertible sofa sleeper & a premium queen sized air mattress. Here, I'd like for you to make yourself at home. You're welcome to raid my... View all property information
    Location Information
    Chicago, Illinois 60601
    1 / 11
    Lakeview
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our updated Lakeview/Lincoln Park apartment features: 4 bedrooms and 2 baths Sleeping for 10 Premier location near shopping, dining and parks Gourmet-inspired kitchen with full appliance package Recently furnished with modern appointments Classic meets contemporary interior WiFi and cable Linens... View all property information
    Location Information
    Chicago, Illinois 60657
    1 / 25
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Whether you are coming to stay at Raffaello Chicago for business, a romantic getaway, or traveling with your family and friends, we have the perfect accommodation ready and waiting for you.<BR><BR>Every Raffaello guest room reflects an upscale European style with soothing accents, subtle earth... View all property information
    Location Information
    Chicago, Illinois 60611
    1 / 21
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    One bedroom apt located in south loop Bronzeville area. Close to McCormick convention center. About 15 mins to Sox stadium.Easy access to public transportation cta bus and train. 15 mins drive to downtown. And Chinatown neighborhood.Walking distance to grocery store jewel. Walgreens .next to la... View all property information
    Location Information
    Chicago, Illinois 60653
    5 of 5 stars Reviewed 15 September 2015
    We got lost coming into the city due to road work and Emmanuel was quick to jump in his car and come to the rescue. He helped us with our bags, gave us recommendations for bars...
    5 of 5 stars Reviewed 16 August 2015
    The host, Emmanuel, was exceptionally friendly and helpful. He was very kind and helped us to the apartment with our bags. We had arrived an hour prior to what we had said as we...
    See all reviews
    1 / 12
    5 of 5 stars (8) Excellent
    Northwest Side
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    This studio is situated in the garden of the property. Very quiet and peaceful setting. It has full bed and a jacuzzi. View all property information
    Location Information
    Chicago, Illinois 60618
    5 of 5 stars Reviewed 19 July 2016
    Great accommodations at the right price!!! Hanne was extremely helpful with how to get from the airport and to Wrigley, providing restaurant recommendations and answering any...
    5 of 5 stars Reviewed 23 August 2015
    this place is really nice. its really clean and comfortable, the room is just perfect. The owner is such a nice person. I will definitely be booking again on my next trip to...
    See all reviews
    1 / 10
    Lakeview
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    PLEASE NOTE: This is not a new property. We have recently left our previous management company, which had been managing this and our other 6 properties for 2+ years. Please see photos for past reviews! Our updated Lincoln Park apartment features: 4 bedrooms and 2 baths Sleeping for 8 Premier... View all property information
    Location Information
    Chicago, Illinois 60657
    1 / 23
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Hot Tub
    • Washer
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    White quartz countertops, two-tone cabinetry, Frigidaire stainless steel appliances, gas stoves and white glass mosaic tile backsplash Full size washer/dryer Custom designed wide plank flooring throughout Walk in closet Contemporary bath finishes Everything about the building has been considered;... View all property information
    Location Information
    Chicago, Illinois 60607
    1 / 38
    Lakeview
    11 Bedrooms, 6 Bathrooms, Sleeps 21 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Patio
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Grill
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Looking for Space? You've Come to the Right Place! Chicago Guest House is the absolute BEST choice for business & leisure travelers who want to experience the sense of having arrived 'home' while they are in Chicago! Beautifully furnished and fully equipped--guaranteed a unique and unforgettable... View all property information
    Location Information
    Chicago, Illinois 60613
    1 / 30
    5 of 5 stars (37) Excellent
    Northwest Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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
    Location Information
    Chicago, Illinois 60625
    5 of 5 stars Reviewed 11 July 2016
    I absolutely loved this place, from the emails I sent to Cheryl ( with her quick responses) to the condo itself. Everything was as advertised. The place was spotless, the little...
    5 of 5 stars Reviewed 19 August 2015
    The owner thought to provide everything you might need. Little things like a few snacks and a fan in the bedroom made the place welcoming from start to finish. Large den space...
    See all reviews
    1 / 8
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Newly built apartment close to Michigan Avenue,Millennium Park, Chicago Theatre,The Art Institute ,Shopping,Movie Theater,Bars and Restaurants. You’ll love my place because of Wonderful view of city living,nice quiet neighborhood, , the comfy bed, the kitchen and the coziness.. My place is good for... View all property information
    Location Information
    Chicago, Illinois 60601
    1 / 19
    Near North Side
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Shared Outdoor Pool...
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    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
    Location Information
    Chicago, Illinois 60611
    1 / 25
    Lakeview
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Patio
    • Housekeeping...
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    The Lakeview neighborhood is an incredible Chicago experience! We live 3 blocks from the Brown Line stop, just a 7 minute walk from Wrigley field, right next door to some amazing Southport Corridor shopping, and terrifically close to a lot of other amazing venues. This apartment is completely... View all property information
    Location Information
    Chicago, Illinois 60657
    1 / 13
    Lincoln Park
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Balcony
    • Air Conditioning
    • Terrace
    • Washer
    • Satellite TV
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Our place is a brand new renovation! You'll love the kitchen, the location, and the coziness. Perfect for couples, solo adventurers, and business travelers. The Victorian row house with the red door is located in the heart of Lincoln Park & walking distance to lots to enjoy (see photos). Our... View all property information
    Location Information
    Chicago, Illinois 60614
    1 / 9
    3 of 5 stars (1) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Large, roomy two bedroom loft like apartment tastefully appointed and furnished. Hardwood floors and ceramic tiles in kitchen and bathroom. Plenty of sitting room with large screen TV, fireplace and free WiFi. Two full bedrooms, one with a king sized and the other with a queen sized bed. You... View all property information
    Location Information
    Chicago, Illinois 60618
    3 of 5 stars Reviewed 2 weeks ago
    Comfortable, large and roomy apartment with good air com and wifi, in a residential area. The apartment is approx 30- 45 mins from the centre of Chicago with very good public...
    See all reviews
    1 / 11
    Lakeview
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our updated Lakeview/Lincoln Park apartment features: 3 bedrooms and 2 baths Sleeping for 8 Premier location near shopping, dining and parks Gourmet-inspired kitchen with full appliance package Recently furnished with modern appointments Classic meets contemporary interior WiFi and cable Linens... View all property information
    Location Information
    Chicago, Illinois 60657
    1 / 21
    5 of 5 stars (1) Excellent
    Lakeview
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Patio
    • Outdoor Dining Area
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Shared Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    An irresistibly charming apartment! Good things do come in small packages! Walk in to the home and the first thing you notice is nothing, absolutely nothing, has been overlooked. You’ll be engulfed in warm inviting hues. The beauty & integrity of the historic Greystone recaptured; undeniably... View all property information
    Location Information
    Chicago, Illinois 60657
    5 of 5 stars Reviewed 15 June 2015
    We were very happy finding this vacation rental. The location was accommodating to our interest. The apartment was excellent. We were able to stay altogether and enjoy the...
    See all reviews
    1 / 11
    4 of 5 stars (4) Very good
    Lakeview
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Shared Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Chicago, Illinois 60657
    5 of 5 stars Reviewed 4 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...
    See all reviews
    1 / 21
    Near North Side
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Terrace
    • Internet Access
    • Washer
    • Balcony
    • DVD Player
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Beautiful open floorplan studio with wall to wall bamboo hardwood flooring, open kitchen with tile backsplash, stainless steel appliances, and granite countertops, huge walk-in closet, floor to ceiling windows exposing city views, updated large bathroom with stone surround, and w/d in unit. Great... View all property information
    Location Information
    Chicago, Illinois 60654
    1 / 41
    5 of 5 stars (23) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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. If you’re heading to Chicago and looking to be near downtown but... View all property information
    Location Information
    Chicago, Illinois 60642
    5 of 5 stars Reviewed 1 week ago
    Wow, it's going to be hard to limit this as start to finish I can't say enough good things. I had never booked this type of vacation rental before and was very nervous that...
    5 of 5 stars Reviewed 25 June 2016
    Our family of five loved our stay at the Magic Factory. The loft is beautifully decorated with great amenities and a comfortable living room for reading or watching movies. If you...
    See all reviews
    1 / 31
    5 of 5 stars (4) Excellent
    Lakeview
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Grill
    • DVD Player
    • Parking
    • Air Conditioning
    • Patio
    • Washer
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Chicago Guest House is the absolute BEST choice for business & leisure travelers who want to experience the sense of having arrived 'home' while they are in Chicago! A Vintage Beauty With All the Modern Comforts & Amenities. Beautifully furnished and fully equipped--guaranteed a unique and... View all property information
    Location Information
    Chicago, Illinois 60657
    5 of 5 stars Reviewed 20 March 2016
    Perfect Accommodations-Perfect Location. Don't miss out on this great lodging experience. Teri the owner is great to work with. She gives you all the resources you need for your...
    5 of 5 stars Reviewed 1 October 2015
    Location, location, location! This place has every creature comfort. The owner and the place is extremely charming. Teri created a relaxing, quiet, peaceful retreat with great...
    See all reviews
    1 / 26
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Washer
    • Balcony
    • Hot Tub
    • Grill
    • Sauna
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Unit not available for daily rental in July 4th Holiday !<BR><BR><BR>*Prices may vary depending on the season. Premium months are between April and September. <BR>*Prices negotiable based on length of stay. Please inquire and we will provide a direct quote for your stay.<BR><BR><BR>MSG ME WITH ANY... View all property information
    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.