Guesthouse accommodation & holiday rentals in Chicago
Find and book unique guesthouse accommodation & rentals on Airbnb
Top-rated Guesthouses in Chicago
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago guesthouses
Family-Friendly guesthouses
Guesthouse in Miller Beach
4.17 out of 5 average rating, 29 reviewsCoach House, Dunes Nat’l Park, 10min hike to Beach
Guesthouse in Wheaton
4.95 out of 5 average rating, 397 reviewsCozy private coach house in Wheaton
Guesthouse in Oak Park
4.88 out of 5 average rating, 461 reviewsCoachhouse in central OP 4 blk to L
Guesthouse in Chicago
4.95 out of 5 average rating, 372 reviewsCozy Coach House
Guesthouse in Chicago
4.88 out of 5 average rating, 252 reviewsThe Rectory
Guesthouses with a patio
Guesthouse in Chicago
4.93 out of 5 average rating, 15 reviewsPrivate Coach House / Easy Commute
Guesthouse in Villa Park
4.83 out of 5 average rating, 47 reviewsTranquil Pondview + New Kitchen + King Bed + WFH
Guesthouse in Merrillville
4.93 out of 5 average rating, 30 reviewsTownhouse with Jacuzzi/Sauna/fireplace
Guesthouse in Chicago
5.0 out of 5 average rating, 36 reviews2 br, 2 bt, detached, UChicago Coachman's House
Guesthouse in Chicago
5.0 out of 5 average rating, 28 reviewsMultiManor: A Renovated Bucktown Coach House
Guesthouse in Wheaton
Guesthouse Adjacent to Wheaton College
Guesthouse in Chicago
4.94 out of 5 average rating, 18 reviewsLogan Square Coach House
Guesthouse in Chicago
4.98 out of 5 average rating, 43 reviewsBotanical BnB. House in Avondale/Logan Square.
Guest house rentals with a washing machine and dryer
Guesthouse in Villa Park
4.9 out of 5 average rating, 81 reviewsEclectic Coach House Apartment
Guesthouse in Chicago
4.94 out of 5 average rating, 89 reviewsQuiet, Cozy 1-Bedroom Carriage House in Chicago
Guesthouse in Oak Park
4.99 out of 5 average rating, 76 reviewsStylish Coachhouse in lovely Oak Park!
Guesthouse in Lake Forest
4.95 out of 5 average rating, 98 reviewsThe Green Door - safe and calm with walkability
Guesthouse in Evanston
4.91 out of 5 average rating, 77 reviewsCozy Guesthouse near NU - next to Lee Street Beach
Guesthouse in Arlington Heights
4.92 out of 5 average rating, 25 reviewsCozy Chicago Suburban Apartment
Guesthouse in Chicago
4.94 out of 5 average rating, 33 reviewsCharming private coach house
Guesthouse in Chicago
4.88 out of 5 average rating, 73 reviewsHidden Cottage in Logan Square
Quick stats about guesthouse rentals in Chicago
Total rentals
70 properties
Wi-Fi availability
70 properties include access to Wi-Fi
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
6.6K reviews
Destinations to explore
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