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 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, 463 reviewsCoachhouse in central OP 4 blk to L
Guesthouse in Chicago
4.95 out of 5 average rating, 373 reviewsCozy Coach House
Guesthouse in Chicago
4.88 out of 5 average rating, 253 reviewsThe Rectory
Guesthouses with a patio
Guesthouse in Chicago
4.94 out of 5 average rating, 16 reviewsPrivate Coach House / Easy Commute
Guesthouse in Villa Park
4.83 out of 5 average rating, 48 reviewsTranquil Pondview + New Kitchen + King Bed + WFH
Guesthouse in Chicago
5.0 out of 5 average rating, 36 reviews2 br, 2 bt, UChicago Coachman's Guesthouse
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 Gary
5.0 out of 5 average rating, 5 reviewsFarm Themed Guesthouse! (NEW)
Guesthouse in Chicago
4.98 out of 5 average rating, 44 reviewsBotanical BnB. House in Avondale/Logan Square.
Guesthouse in Chicago
4.95 out of 5 average rating, 19 reviewsLogan Square Coach House
Guest house rentals with a washing machine and dryer
Guesthouse in Chicago
4.94 out of 5 average rating, 90 reviewsQuiet, Cozy 1-Bedroom Carriage House in Chicago
Guesthouse in Oak Park
4.99 out of 5 average rating, 77 reviewsStylish Coachhouse in lovely Oak Park!
Guesthouse in Evanston
4.91 out of 5 average rating, 78 reviewsCozy Guesthouse near NU - next to Lee Street Beach
Guesthouse in Chicago
4.88 out of 5 average rating, 75 reviewsHidden Cottage in Logan Square
Guesthouse in Arlington Heights
4.92 out of 5 average rating, 26 reviewsCozy Chicago Suburban Apartment
Guesthouse in Chicago
4.94 out of 5 average rating, 33 reviewsCharming private coach house
Guesthouse in Chicago
4.98 out of 5 average rating, 80 reviewsPrivate Historic Coach House Wicker Park
Guesthouse in Evanston
4.93 out of 5 average rating, 100 reviewsHistoric Coach House in Evanston Near Beach & Town
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
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Accommodation & holiday rentals
- Lake Michigan Beach Accommodation & holiday rentals
- Saugatuck Accommodation & holiday rentals
- Evanston Accommodation & holiday rentals
- Holland Accommodation & holiday rentals
- South Haven Holiday rentals
- Naperville Accommodation & holiday rentals
- South Side Accommodation & holiday rentals
- South Bend Accommodation & holiday rentals
- New Buffalo Holiday rentals
- House rentals United States
- Guesthouse rentals United States
- Condo rentals Chicago
- Rentals with a hot tub Chicago
- Townhouse rentals Chicago
- Bed and breakfasts Chicago
- Rentals with a washing machine and dryer Chicago
- Kid-friendly rentals Chicago
- Lakehouse rentals Chicago
- Loft rentals Chicago
- Rentals with lake access Chicago
- Rentals with an accessible height toilet Chicago
- Rentals with a home theatre Chicago
- Rentals with outdoor seating Chicago
- House rentals Chicago
- Rentals with pools Chicago
- Rentals with beach access Chicago
- Private suite rentals Chicago
- Apartment rentals Chicago
- Rentals with an EV charger Chicago
- Smoking-friendly rentals Chicago
- Mansion rentals Chicago
- Beachfront rentals Chicago
- Family-friendly rentals Chicago
- Boutique hotel rentals Chicago
- Rentals with a fireplace Chicago
- Rentals with an accessible height bed Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Monthly Rentals Chicago
- Rentals with a patio Chicago
- Rentals with breakfast Chicago
- Rentals with a fire pit Chicago
- Rentals with a sauna Chicago
- Waterfront rentals Chicago
- Fitness-friendly rentals Chicago
- Rentals with a balcony Chicago
- House rentals Downtown Chicago
- House rentals Milwaukee
- House rentals Lake Geneva
- Guesthouse rentals Illinois
- House rentals Illinois
- Guesthouse rentals Cook County
- House rentals Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom