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
Room in Winfield
4.95 out of 5 average rating, 62 reviewsCountry Retreat, 2 Block walk to Metra Train
17–24 Feb
Room in Evanston
4.97 out of 5 average rating, 519 reviewsClassy and Cozy home in Evanston
3–10 Aug
Room in Chicago
4.95 out of 5 average rating, 213 reviewsGreat Edgewater/Andersonville private suite
30 Aug – 6 Sept
Room in Evanston
4.95 out of 5 average rating, 425 reviewsClassy and Cozy 2nd. Room
2–9 Apr
Room in Chicago
4.99 out of 5 average rating, 102 reviewsLovely UofC Prof mansion great on campus location
26 Sept – 3 Oct
Room in Chicago
4.95 out of 5 average rating, 147 reviewsWrigleyville Private Twin Bedroom w/ Private Bath
8–15 Jul
Bed and breakfast rentals with breakfast
Room in Palatine
4.92 out of 5 average rating, 184 reviewsQuiet Primary King Bed, Kitchen & Private Bathroom
14–21 Jun
Room in Evanston
4.67 out of 5 average rating, 66 reviewsHuge (2Beds) 1 Bedroom
18–25 Jun
Room in Mokena
4.94 out of 5 average rating, 71 reviewsPrivate home in Mokena - Room 2
11–18 Aug
Shared room in Wheeling
17 Miles to downtown
3–10 Dec
Room in Chicago
4.95 out of 5 average rating, 98 reviewsTop location, sunny UofC Prof on campus home
29 Oct – 5 Nov
Hotel room in Chicago
4.91 out of 5 average rating, 43 reviewsKing Room in Boutique Wicker Park B&B
11–18 Oct
Room in Chicago
5.0 out of 5 average rating, 63 reviewsHistoric campus U of C Prof. mansion, top location
18–25 Mar
Room in Chicago
4.92 out of 5 average rating, 50 reviewsHistoric campus house owned by U of C Prof
29 Aug – 5 Sept
Quick stats about bed and breakfast rentals in Chicago
Total rentals
80 properties
Wifi availability
70 properties include access to wifi
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Total number of reviews
4.8K reviews
Nightly prices starting at
£16 before taxes and fees
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Bed and breakfasts United States
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- Rentals with a hot tub Chicago
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