Guesthouse vacation rentals in Chicago
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Chicago
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago guesthouse rentals
Family-friendly guest house rentals
Guesthouse
4.89 out of 5 average rating, 484 reviewsCoachhouse in central OP 4 blk to L
Guesthouse
4.87 out of 5 average rating, 279 reviewsThe Rectory
Guesthouse
4.95 out of 5 average rating, 407 reviewsCozy Coach House
Guesthouse
4.95 out of 5 average rating, 439 reviewsCozy private coach house in Wheaton
Guesthouse
4.94 out of 5 average rating, 168 reviewsCoach House Art Studio, By Downtown & Northwestern
Guest house rentals with a patio
Guesthouse
4.9 out of 5 average rating, 42 reviewsLogan Square Coach House
Guesthouse
4.96 out of 5 average rating, 27 reviewsSolar Victorian MCM Coach House
Guesthouse
4.98 out of 5 average rating, 66 reviewsBotanical BnB. House in Avondale/Logan Square.
Guesthouse
5 out of 5 average rating, 3 reviewsGuesthouse Adjacent to Wheaton College
Guesthouse
4.93 out of 5 average rating, 14 reviewsGreen #3
Guesthouse
4 out of 5 average rating, 6 reviewsCozy and Private Home
Guesthouse
4.86 out of 5 average rating, 70 reviewsTranquil Pondview + New Kitchen + King Bed + WFH
Guesthouse
5 out of 5 average rating, 61 reviews2 br, 2 bt, UChicago Coachman's Guesthouse
Guest house rentals with a washer and dryer
Guesthouse
5 out of 5 average rating, 25 reviewsMitra Guest House
Guesthouse
4.93 out of 5 average rating, 44 reviewsCozy Chicago Suburban Apartment
Guesthouse
4.88 out of 5 average rating, 58 reviewsHome Sweet Home
Guesthouse
4.92 out of 5 average rating, 96 reviewsCozy Guesthouse near NU - next to Lee Street Beach
Guesthouse
4.95 out of 5 average rating, 41 reviewsCharming private coach house
Guesthouse
4.98 out of 5 average rating, 88 reviewsPrivate Historic Coach House Wicker Park
Guesthouse
4.9 out of 5 average rating, 89 reviewsHidden Cottage in Logan Square
Guesthouse
4.85 out of 5 average rating, 13 reviewsWhimsical Cottage......Brand new construction
Quick stats about guesthouse rentals in Chicago
Total rentals
70 properties
Total number of reviews
7.3K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wifi availability
70 properties include access to wifi
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