
Bed and breakfast vacation rentals in Chicago
Find and book unique bed and breakfast rentals on Airbnb
Quick stats about bed and breakfast rentals in Chicago

Total vacation rentals
Explore 70 vacation rentals in Chicago

Nightly prices starting at
Chicago vacation rentals start at $50 per night before taxes and fees

Verified guest reviews
Over 5,540 verified reviews to help you choose

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
70 of Chicago vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chicago rentals

4.7 Average rating
Chicago stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Chicago's top spots, include Millennium Park, Wrigley Field, and Lincoln Park
Top-rated bed and breakfast rentals in Chicago
Guests agree: these bed and breakfast rentals are highly rated for location, cleanliness, and more.

Historic campus U of C Prof. mansion, top location
NO closer location to the Univ. of Chicago. This large on-campus master suite features beautiful hardwood oak floors, big windows overlooking the front of the house, luxurious sauna bath, glass enclosed shower, heated bathroom floors, dressing area, vintage ladies dressing table and cheval mirror, work desk, and Cal King bed. Minutes from dorms and main campus. Large shared kitchen and deck. See all 5 rooms avail. in our bed and breakfast: here:https://airbnb.com/users/143937691/listings
ValueLocationView

Bright Room with a Garden View
Located in the middle of the vibrant Boystown community, we are located close to many bars and restaurants, a 10 minute walk to Wrigley Field, and close to make public transit spots to get anywhere. This Bed and Breakfast offers a continental breakfast each morning, smart tvs in each room and free wifi. Parking permits for the surrounding area. Free bag drop off. Shares bathroom with 2 rooms Room service and Cubs Game and Concert Day Specials provided to our guest next door at Big Gay Sal's
ValueLocationBeach

(BR#1) Welcoming, warm & comfortable, 3 guests
Welcoming, warm & comfortable home, BR#1 for up to 3 guests. (LISTING #1 OF 3; see other listings for additional space.) A lovely and spacious bedroom in our home. Located close to Hwy 94. 10 miles from Chicago, close to beach & Wilmette, Evanston, Glenview, Skokie. You're welcome to use all the facilities - kitchen, bathrooms, TV, hi-speed Wifi, laundry & parking. Make your breakfast with supplied basics such as cereal, eggs, juice, tea & coffee. Meaningful conversation (if you want it).
ValueFamilyWifi

Lincoln Park Guest House
Bed and Breakfast license issued by the City of Chicago # 2398451. Hosts live onsite. The private guest suite features a two-story cathedral ceiling with skylights, king bed is upholstered in leather with a memory foam mattress and premium Vera Wang linens. Private bath with personal amenities. mini-refrigerator stocked with bottled water and and a Keurig machine with coffee. Daily housekeeping provided. Property not ADA accessible. Thirteen steps lead from street level to front door.
LocationSleep qualityBathroom

Great Edgewater/Andersonville private suite
1904 Greystone 2-Flat gut rehabbed into Single Family Home: Loft style w/ exposed brick & duct work. Private guest suite (w/ separate entrance) that sleeps 2-4 persons, There is a King bed in the private bedroom & queen tempurpedic topped sofa sleeper in the private living area, wet bar w/ mini fridge, Keurig coffee maker, sink and microwave, 2 flat screens TVs, private bath, piano, and use of the backyard garden. Also, the main house Kitchen/Living Rm are available to use upon request
LocationFamilyIndoor spaces

Urban Oasis Pilsen - guest room in townhouse
Experience the charm of Pilsen, one of Chicago's trendiest neighborhoods. Your private bedroom features a queen-size bed and an en-suite bathroom with a tub/shower. The room includes a small desk, ample storage space, and a TV with streaming services. Triple-paned windows provide plenty of natural light while minimizing noise from the nearby I-90/94 freeway. The room is located on the third floor (40 steps)! The second floor offers access to the kitchen, living room, and balcony.
ValueLocationSolo travel

Blue Room in Dorothy's BNB
Located right in the middle of Boystown in the Lakeview this room has a queen bed with two shared bathrooms. Central ac and heat. Wifi, continental breakfast, included. The space has a shared kitchen, washer and dryer, living room, dining area. This space is shared with three other bedrooms and is located right off Halsted street, so if you are sensitive to noise, this may not be the right room for you. There is no parking on site, street parking only, permits available.
ValueLocationHospitality

Large private room w/ shared bathroom in Boystown!
Located in the middle of the vibrant Boystown community, we are located close to many bars and restaurants, a 10 minute walk to Wrigley Field, and close to make public transit spots to get anywhere. This Bed and Breakfast offers a continental breakfast each morning, smart tvs in each room and free wifi. Parking permits for the surrounding area. Free bag drop off Room service and Cubs Game and Concert Day Specials provided to our guest next door at Big Gay Sal's
FamilyValueQuiet

Sun-Filled King Room in Boutique Wicker Park B&B
Bright and modern guest room located on the second floor with a lovely view of our quiet, tree-lined street. Just a block away from great dining, vintage and boutique shopping, art galleries, cool cafes and vibrant nightlife. The Concord King guest room is one of 9 rooms within the Wicker Park Inn, a newly renovated, boutique Bed and Breakfast offering high quality yet affordable accommodations in a hip & trendy neighborhood.
LocationCheck-inComfort

SuperHost with Private bedroom/bath/entry Lakeview
Fun, vibrant residential neighborhood surrounded by bars, theaters, coffee shops, restaurants and boutiques. Private access to a one bed/bath with additional access to the bright spacious family room. Located minutes from bus, DIVVY bikes, and "el" (2 blocks), Wrigley Field (6 blocks) and 1.5 miles to Lake Michigan. Walk Approximately 20 minutes by train to the downtown area or central city "Loop."
ValueFamilyBreakfast

#7 Historic Chicago Home - Bunk Bedroom(Twin&Full)
The Greenleaf House, built in 1915, is our 3600ft² home with 6 bedrooms, 2.5 baths, & an open floor plan - perfect for gatherings of any kind. We're in the heart of the Rogers Park, walking distance from many restaurants & shops, one block from Loyola Beach Park, and 5-15 mins walk to 2 different train / metro lines. The home is run by friendly local folks who are happy to help during your stay.
FamilyLocationAccuracy

Villa Dubois Guest House Room 1
Villa Dubois Guest House is great for couples, solo adventurers, and business travelers. Experience the comfortable and casual vibe, just minutes away from local restaurants, downtown, public transit (both bus and train), Divvy Bike Stations, and McCormick Convention Center. Room 1 is a private room with shared bathroom for up to 2 guests. It is one of our largest and brightest room.
LocationValueParking
Popular amenities for Chicago bed and breakfast rentals
Family-friendly bed and breakfast rentals

Private bedroom with shared bath
LocationValueGetting around

Historic campus house owned by U of C Prof
ValueLocationIndoor spaces

Private ensuite bedroom and bathroom
LocationValueCleanliness

Luxurious King Room in Boutique Wicker Park B&B
LocationHospitalityCheckout

Spacious King Room in Boutique Wicker Park B&B
LocationDecorGetting around

Romantic King Room in Boutique Wicker Park B&B
LocationValueWalkability

Romantic Queen Room in Boutique Wicker Park B&B
LocationQuietBreakfast

Wrigleyville Suites Room 1
LocationValueNearby
Bed and breakfast rentals with breakfast

Lovely UofC Prof mansion great on campus location
LocationValueKitchen

Cute room in downtown Boystown
ValueLocationLaundry

Queen Bed with Private Bath in Boystown
FamilyLocationWalkability

British Themed Room in the Middle of Boystown
ValueLocationAir conditioning

Cozy Garden Room in the middle of Boystown!
LocationFamilyBreakfast

Private room with private entrance in Boystown
LocationValueLaundry

Top location, sunny UofC Prof on campus home
FamilyValueKitchen

Queen Room w/ Balcony in Boutique Wicker Park B&B
FamilyLocationView
Other bed and breakfast vacation rentals

Villa Dubois Guest House Room 3
ValueLocationCheck-in

House 5863 Bed and Breakfast Room 3
LocationQuietAmenities

Dubois Guest House Room 101
LocationValueCheckout

Historic campus U of C Prof. mansion, top location
FamilyValueBreakfast

Bright Room with a Garden View
LocationValueAccess

Large private room w/ shared bathroom in Boystown!
FamilyValueLayout

Great Edgewater/Andersonville private suite
ValueLocationAccuracy

(BR#1) Welcoming, warm & comfortable, 3 guests
ValueFamilyCheck-in
When is the best time to visit Chicago?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $120 | $101 | $141 | $142 | $185 | $217 | $119 | $131 | $114 | $108 | $107 | $98 |
| Avg. temp | 26°F | 30°F | 40°F | 51°F | 62°F | 72°F | 76°F | 75°F | 68°F | 55°F | 42°F | 31°F |
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