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.

The Chicago House

  • Free Parking
Apr 9 Apr 10
1 room, 2 adults, 0 children
Our online travel partners don't provide prices for this accommodation, but we can search other options in ProvincetownSee available hotels in Provincetown
6 Winslow St, Provincetown, MA 02657-1437
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
09/04/2017 10/04/2017
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    Write a Review
    Turn Your Opinions into Points!
    Turn your opinions into JPMiles
    Turn your opinions into PAYBACK Points
    *You can enroll in only one programme at a time to earn rewards for reviews.
    JPMiles / Payback Arrow
    JPMiles / PAYBACK
    Traveller rating
    Traveller type
    Time of year
    All reviews b b home away from home a great stay chris wifi dogs guests town
    Reviewed 31 August 2016

    From the moment I arrived, I felt like Chicago House was home. Craig was amazing--warm, friendly and doing everything in his power to make me feel comfortable. Yummy continental breakfast, old-world charm, a comfy bed, air-conditioning as needed, and wifi. Who could ask for anything...More

    Reviewed 23 August 2016

    We had a great stay at the Chicago House. Our room was not fancy but very comfortable. There were made place inside the house and outside to read. Craig was very helpful and friendly and made our stay very enjoyable.

    Reviewed 18 July 2016

    Mediocre old BnB now that there are new owners that aren't on site . After staying there a few years in a row, will never go back. The live in employee is only there to do a job and couldn't care less about customer's concerns

    Reviewed 8 May 2016 via mobile

    The proprietor, Chris is a real gem. He bent over backwards to be accommodating and is a really sweet fellow. The house itself is what I would refer to as 'old school Provincetown'. This is like a home from home, especially if you are an...More

    Reviewed 16 July 2015

    The Chicago House is in the perfect location--practically in the center of town but on a side street so you're away from the heavy traffic of Bradford and Commercial Streets. The rooms are clean, quiet, and comfortable. The front and back porches are great for...More

    • Top amenities
    • Free Parking
    • Hotel Amenities
    • Free Parking
    • Room amenities
    • Air Conditioning
    {"widget":{"name":"ibex_photo_carousel","template":"ibex_photo_carousel__widget","dust":{"nav_controls":"ibex_photo_carousel__nav_controls"},"divClasses":"prw_rup prw_ibex_photo_carousel","moduleList":["handlers"],"js":{"handlers":"(ta.prwidgets.getjs(this,'handlers'))"}},"scriptFlags":null,"containerClass":null}
    View from Room (3)
    Room/Suite (3)
    Hotel & Grounds (3)
    Dining (1)
    Nearby Restaurants
    502 reviews
    .18 km away
    Tin Pan Alley
    293 reviews
    .14 km away
    Provincetown Portuguese Bakery
    434 reviews
    .22 km away
    Ross' Grill
    352 reviews
    .18 km away
    Nearby Attractions
    Commercial Street
    1,547 reviews
    .14 km away
    Pilgrim Monument & Provincetown Museum
    992 reviews
    .11 km away
    Provincetown Town Hall
    151 reviews
    .10 km away
    Cortile Gallery
    11 reviews
    .13 km away
    Questions & Answers
    Get quick answers from The Chicago House staff and past guests.
    Note: your question will be posted publicly on the Questions & Answers page.
    Posting guidelines
    Room Tips
    "Chris, the owner, is very approachable, just ask."
    davidmoorman, over a year agoRead review
    "Many rooms have shared baths. If you are particular, ask for one with a private bath. Room 5 was wonderful!"
    jfm02719, over a year agoRead review
    "Room 5 - Large Kind with Private Bathroom"
    PJackkand, over a year agoRead review
    "Room 5 - King Bed as more leg room. Room 5- has the best bathroom (size)"
    PJackkand, over a year agoRead review
    "Stayed in upstairs room in back, but think all are just as good, cute and comfy..."
    jcumiami, over a year agoRead review
    Similar nearby hotels
    Masthead Resort