A river with a yellow boat, surrounded by tall buildings and a bridge.

Search Guest Houses in Chicago

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
31 Jul - 2 Aug
In two weeks
7 Aug - 9 Aug
In one month
21 Aug - 23 Aug
In two months
18 Sep - 20 Sep

Our top choices for Chicago guest houses

Exterior

Chicago Avenue Inn

Chicago Avenue Inn
2.0 star property
Humboldt Park
7.0 out of 10, Good, (105 reviews)
"Only quip was door wouldn’t unlock had to call for a code. Limited kitchen supplies so cooking was hard. Also area is pretty dangerous at night. Would not recommend to new travelers or people who don’t know the area"
United States
Zoe
The price is ฿2,479
฿4,949 total
includes taxes & fees
17 Aug - 18 Aug
Chicago Avenue Inn
Living area

Villa Dubois Guest House

Villa Dubois Guest House
2.0 star property
Bronzeville
7.8 out of 10, Good, (116 reviews)
"Fantastic stay, easy to find, relatively close to the L"
United States
Steven
The price is ฿4,567
฿5,362 total
includes taxes & fees
11 Aug - 12 Aug
Villa Dubois Guest House
Lobby lounge

The Plainfield Inn

The Plainfield Inn
3.0 star property
Plainfield
9.8 out of 10, Exceptional, (177 reviews)
"The room is very clean and quiet. Close to dining."
United States
Doug
The price is ฿3,380
฿3,751 total
includes taxes & fees
2 Aug - 3 Aug
The Plainfield Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chicago Hotel Reviews

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

8/10 Good
"The location was good for the Art Institute, Millenium Park, and shopping at Macy's, The subway access was excellent except that they were doing maintenance when I arrived. The hotel was frequented by business customers but we were there for pleasure. Room cleaning goes on until 5 pm, which is fine for business people gone all day and half the night. Not so for us, who wanted to take afternoon nap after walking in a hot humid city. If I had been told that, I would have requested early cleaning. We were gone from the room 5 or 6 hours at a clip and would still come back to a dirty room and no clean towels. My partner had to chase a maid down the hall and beg for clean towels, utilizing her Spanish skills. The speakeasy bar makes very strong drinks."
Virginia 4-night trip
Posted 1 hour ago
Palmer House a Hilton Hotel

Find out more about Chicago

Chicago Guest Houses information

Number of reviews
221
Accommodation
7 Guest Houses
Lowest Price
฿3,751
Highest Price
฿5,362