
Bed and breakfast holiday rentals in Chicago
Find and book unique bed & breakfast rentals on Airbnb
Top-rated bed and breakfast rentals in Chicago
Guests agree: these bed and breakfast rentals 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 bed & breakfast rentals in Chicago
Family-friendly bed & breakfast rentals

Private room in Hyde Park
4.99 out of 5 average rating, 108 reviewsLovely UofC Prof mansion great on campus location

Private room in Evanston
4.97 out of 5 average rating, 566 reviewsClassy and Cozy home in Evanston

Private room in East Rogers Park
4.8 out of 5 average rating, 172 reviews#7 Historic Chicago Home - Bunk Bedroom(Twin&Full)

Private room in East Rogers Park
4.82 out of 5 average rating, 168 reviews#4 Historic Chicago Home - Private Single Bedroom

Private room in Andersonville
4.95 out of 5 average rating, 250 reviewsGreat Edgewater/Andersonville private suite

Private room in Evanston
4.95 out of 5 average rating, 484 reviewsClassy and Cozy 2nd. Room
Bed and breakfast rentals with breakfast

Hotel room in Wicker Park
5 out of 5 average rating, 6 reviewsRomantic Queen Room in Boutique Wicker Park B&B

Private room in Hyde Park
5 out of 5 average rating, 81 reviewsHistoric campus U of C Prof. mansion, top location

Private room in Hyde Park
4.93 out of 5 average rating, 61 reviewsHistoric campus house owned by U of C Prof

Hotel room in Wicker Park
5 out of 5 average rating, 5 reviewsSun-Filled King Room in Boutique Wicker Park B&B

Hotel room in Wicker Park
4.85 out of 5 average rating, 48 reviewsQueen Room w/ Balcony in Boutique Wicker Park B&B

Private room in Norwood Park
4.78 out of 5 average rating, 266 reviewsCloudgate Room, minutes to O'Hare in Safest Area

Hotel room in Wicker Park
4.82 out of 5 average rating, 28 reviewsRomantic King Room in Boutique Wicker Park B&B

Hotel room in Wicker Park
4.75 out of 5 average rating, 4 reviewsLuxurious King Room in Boutique Wicker Park B&B
Quick stats about bed and breakfast rentals in Chicago
Total rentals
60 properties
Nightly prices starting at
$40 SGD before taxes and fees
Total number of reviews
2.2K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wifi availability
60 properties include access to wifi
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- Lake Michigan Beach Holiday rentals
- South Side Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Saugatuck Holiday rentals
- Bed and breakfasts United States
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