Bed and breakfast holiday rentals in Chicago
Find and book unique bed and breakfasts on Airbnb
Top-rated bed and breakfasts 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 Chicago bed and breakfasts
Family-Friendly Bed and Breakfasts
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 July
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 June
Room in Evanston
4.67 out of 5 average rating, 66 reviewsHuge (2Beds) 1 Bedroom
18 – 25 June
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
Wi-Fi availability
70 properties include access to Wi-Fi
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
$31 AUD before taxes and fees
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
- Bed and breakfasts United States
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