
Bed and breakfast vacation rentals in Chicago
Find and book unique bed and 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.

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

(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).

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

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.

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.

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

Queen Bed with Private Bath 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

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.

Loft Style Private Apt 2 (1 Room- 420 Friendly)
Please do not book unless you read the entire listing, including all house rules & amenities. No refunds will be given if you book without first reading the house rules Near Loyola University. 420 friendly environment. No Cleaning Fee, Full Kitchen, Living Room, 1 Shared Bathroom, Internet, Heat, Air Conditioning Redline, CTA, Beach, Groceries, Gyms, Multiple Bars & Diverse Cuisine within 5-15 min walking

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."

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.

Classy and Cozy 2nd. Room
2nd. Room available quiet suburban Evanston close to dowontown. Comfortable for two. Bathroom, full bed, closet, chests. street parking always available. Original art, books, Old World decor, wifi, personalized attention, delicious hearty breakfast. We are Covid-19 compliant and fully vaccinated.
Popular amenities for Chicago bed and breakfast rentals
Family-friendly bed and breakfast rentals

Private room with private entrance in Boystown

Historic campus U of C Prof. mansion, top location

Great Edgewater/Andersonville private suite

Large private room w/ shared bathroom in Boystown!

Urban Oasis Pilsen - guest room in townhouse

Lovely UofC Prof mansion great on campus location

(BR#1) Welcoming, warm & comfortable, 3 guests

SuperHost with Private bedroom/bath/entry Lakeview
Bed and breakfast rentals with breakfast

Private room with private entrance in Boystown

Cute room in downtown Boystown

Queen Bed with Private Bathroom in Boystown

Historic campus house owned by U of C Prof

Bright Room with a Garden View

Queen Room w/ Balcony in Boutique Wicker Park B&B

Lovely UofC Prof mansion great on campus location

Cozy Garden Room in the middle of Boystown!
Other bed and breakfast vacation rentals

Cute room in downtown Boystown

Historic campus U of C Prof. mansion, top location

Great Edgewater/Andersonville private suite

Large private room w/ shared bathroom in Boystown!

Urban Oasis Pilsen - guest room in townhouse

Lovely UofC Prof mansion great on campus location

(BR#1) Welcoming, warm & comfortable, 3 guests

SuperHost with Private bedroom/bath/entry Lakeview
When is the best time to visit Chicago?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$25,086 GYD | G$21,114 GYD | G$29,476 GYD | G$19,024 GYD | G$22,577 GYD | G$25,295 GYD | G$24,877 GYD | G$27,386 GYD | G$23,832 GYD | G$22,577 GYD | G$22,368 GYD | G$20,487 GYD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
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 G$10,453 GYD per night before taxes and fees

Verified guest reviews
Over 5,250 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
Destinations to explore
- Platteville Vacation rentals
- Indianapolis Vacation rentals
- Downtown Chicago Vacation rentals
- Louisville Vacation rentals
- Detroit Vacation rentals
- Southern Indiana Vacation rentals
- Columbus Vacation rentals
- St. Louis Vacation rentals
- Cincinnati Vacation rentals
- Wisconsin River Vacation rentals
- Milwaukee Vacation rentals
- Windsor Vacation rentals
- Rentals with beach access Chicago
- Boutique hotels Chicago
- Beachfront rentals Chicago
- Apartment rentals Chicago
- Rentals with an accessible height bed Chicago
- Loft rentals Chicago
- Rentals with breakfast Chicago
- Rentals with a fire pit Chicago
- Luxury rentals Chicago
- Waterfront rentals Chicago
- Rentals with an EV charger Chicago
- Rentals with a home theater Chicago
- Rentals with outdoor seating Chicago
- Smoking-friendly rentals Chicago
- House rentals Chicago
- Rentals with a washer and dryer Chicago
- Townhouse rentals Chicago
- Rentals with a patio Chicago
- Rentals with a balcony Chicago
- Fitness-friendly rentals Chicago
- Lakehouse rentals Chicago
- Rentals with a fireplace Chicago
- Mansion rentals Chicago
- Serviced apartment rentals Chicago
- Family-friendly rentals Chicago
- Condo rentals Chicago
- Rentals with a hot tub Chicago
- Rentals with pools Chicago
- Guesthouse rentals Chicago
- Rentals with a sauna Chicago
- Rentals with lake access Chicago
- Private suite rentals Chicago
- Hotel rooms Chicago
- Pet-friendly rentals Chicago
- Bed and breakfasts Cook County
- Bed and breakfasts Illinois
- Bed and breakfasts United States
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Union Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Washington Park Zoo
- Oak Street Beach
- Museum of Science and Industry
- Illinois Beach State Park
- Willis Tower
- Indiana Dunes State Park
- Things to do Chicago
- Nature and outdoors Chicago
- Sightseeing Chicago
- Food and drink Chicago
- Art and culture Chicago
- Sports activities Chicago
- Tours Chicago
- Things to do Cook County
- Food and drink Cook County
- Sports activities Cook County
- Tours Cook County
- Sightseeing Cook County
- Art and culture Cook County
- Nature and outdoors Cook County
- Things to do Illinois
- Art and culture Illinois
- Food and drink Illinois
- Sports activities Illinois
- Nature and outdoors Illinois
- Sightseeing Illinois
- Tours Illinois
- Things to do United States
- Tours United States
- Sightseeing United States
- Art and culture United States
- Wellness United States
- Food and drink United States
- Nature and outdoors United States
- Entertainment United States
- Sports activities United States







