Guesthouse vacation rentals in Chicago
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouses in Chicago
Guests agree: these guesthouses 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 guesthouses
Family-friendly guesthouses
Guesthouse in Wheaton
4.95 out of 5 average rating, 388 reviewsCozy private coach house in Wheaton
Apr. 1 – 8
Guesthouse in Oak Park
4.88 out of 5 average rating, 457 reviewsCoachhouse in central OP 4 blk to L
Feb. 6 – 13
Guesthouse in Chicago
4.95 out of 5 average rating, 367 reviewsCozy Coach House
Aug. 19 – 26
Guesthouse in Chicago
4.88 out of 5 average rating, 251 reviewsThe Rectory
Jul. 10 – 17
Guesthouses with a patio
Guesthouse in Merrillville
4.93 out of 5 average rating, 28 reviewsTownhouse with Jacuzzi/Sauna/fireplace
Dec. 30 – Jan. 6
Guesthouse in Villa Park
4.83 out of 5 average rating, 42 reviewsTranquil Pondview + New Kitchen + King Bed + WFH
Oct. 19 – 26
Guesthouse in Chicago
5.0 out of 5 average rating, 36 reviews2 br, 2 bt, detached, UChicago Coachman's House
Dec. 29 – Jan. 5
Guesthouse in Chicago
5.0 out of 5 average rating, 27 reviewsMultiManor: A Renovated Bucktown Coach House
Sep. 13 – 20
Guesthouse in Wheaton
Guesthouse Adjacent to Wheaton College
Jan. 3 – 10
Guesthouse in Chicago
4.75 out of 5 average rating, 36 reviewsHistoric Washington-Hyde Park Greystone
Sep. 4 – 11
Guesthouse in Chicago
4.94 out of 5 average rating, 17 reviewsLogan Square Coach House
Sep. 9 – 16
Guesthouse in Chicago
4.98 out of 5 average rating, 41 reviewsBotanical BnB. House in Avondale/Logan Square.
Oct. 20 – 27
Guesthouse rentals with a washer and dryer
Guesthouse in Villa Park
4.92 out of 5 average rating, 74 reviewsEclectic Coach House Apartment
Sep. 16 – 23
Guesthouse in Chicago
4.94 out of 5 average rating, 84 reviewsQuiet, Cozy 1-Bedroom Carriage House in Chicago
Sep. 28 – Oct. 5
Guesthouse in Evanston
4.91 out of 5 average rating, 76 reviewsCozy Guesthouse near NU - next to Lee Street Beach
Mar. 22 – 29
Guesthouse in Oak Park
4.99 out of 5 average rating, 73 reviewsStylish Coachhouse in lovely Oak Park!
Apr. 18 – 25
Guesthouse in Chicago
4.97 out of 5 average rating, 79 reviewsPrivate Historic Coach House Wicker Park
Aug. 21 – 28
Guesthouse in Chicago
4.94 out of 5 average rating, 32 reviewsCharming private coach house
Nov. 10 – 17
Guesthouse in Chicago
4.9 out of 5 average rating, 50 reviewsCharming Logan Square Coach House
Aug. 12 – 19
Guesthouse in Evanston
4.94 out of 5 average rating, 97 reviewsHistoric Coach House in Evanston Near Beach & Town
Sep. 20 – 27
Quick stats about guesthouse rentals in Chicago
Total rentals
70 properties
Wifi availability
70 properties include access to wifi
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
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