
Bed and breakfast vacation 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.

Lovely UofC Prof mansion great on campus location
No closer accommodation to U of C anywhere. Large light filled bedrooms, private bathrooms, huge balcony in 4 story light filled home on sought after University of Chicago campus. Two blocks from the University, four blocks from Lab school. Short walk to train to downtown, beach, bike path, Science and Industry Museum and lakefront. A rare, privately owned home in the heart of campus. See all five rooms available in our lovely bed and breakfast here:https://airbnb.com/users/143937691/listings

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

Top location, sunny UofC Prof on campus home
NO closer accommodation to the U of c campus, large wrap around deck with garden and small semi private deck. convenient access to lakefront, Obama house, Science and Industry museum, public transport. Excellent do it yourself morning breakfast in large kitchen, sparkling clean home. Newly renovated room, marble bathroom floors. More like a traditional bed and breakfast than airbnb. See all five rooms available in our lovely 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).

Cute room in downtown 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

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

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."

Wrigleyville Suites Room 1
Wrigleyville Suites are 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 Cubs Stadium. Room 1 is a private room with a queen bed and shared bathroom for up to 2 guests. It is one of our largest and brightest room.

Private bedroom with shared bath
Located in the heart of Boystown, this private room has a full sized bed, shares two bathrooms with three other rooms, shared kitchen, shared living room and dining room. Wifi throughout the property. Main thing to be aware of, is due to its centrality, it can be loud, especially at night on weekends. Weekly cleaning of all shared spaces included.

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.

Cloudgate Room, minutes to O'Hare in Safest Area
My other listing can be found through my profile. This room is just next to the washroom. My place is only 1 mile/1.6km to USMLE Center; 10 minutes driving to O'Hare, 0.6 miles to CTA Blue Line station. Early check in is available for an additional fee. Prices are subject to change.
Popular amenities for Chicago bed and breakfasts
Family-friendly bed and breakfasts

Cute room in downtown Boystown

Bright Room with a Garden View

Large private room w/ shared bathroom in Boystown!

Lovely UofC Prof mansion great on campus location

Cozy Garden Room in the middle of Boystown!

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

SuperHost with Private bedroom/bath/entry Lakeview

Top location, sunny UofC Prof on campus home
Bed and breakfast rentals with breakfast

Romantic Queen Room in Boutique Wicker Park B&B

Private room with private entrance in Boystown

Queen Bed with Private Bathroom in Boystown

Sun-Filled King Room in Boutique Wicker Park B&B

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

Romantic King Room in Boutique Wicker Park B&B

Luxurious King Room in Boutique Wicker Park B&B

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

Private room with private entrance in Boystown

Cute room in downtown Boystown

Bright Room with a Garden View

Large private room w/ shared bathroom in Boystown!

Lovely UofC Prof mansion great on campus location

Cozy Garden Room in the middle of Boystown!

(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 | $166 CAD | $140 CAD | $195 CAD | $126 CAD | $149 CAD | $167 CAD | $165 CAD | $181 CAD | $158 CAD | $149 CAD | $148 CAD | $136 CAD |
| 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 $69 CAD 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

Wifi availability
70 of Chicago vacation rentals include wifi 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
- Columbus Vacation rentals
- Louisville Vacation rentals
- Detroit Vacation rentals
- Southern Indiana Vacation rentals
- St. Louis Vacation rentals
- Cincinnati Vacation rentals
- Milwaukee Vacation rentals
- Wisconsin River Vacation rentals
- Windsor Vacation rentals
- Rentals with a patio Chicago
- Rentals with an accessible height bed Chicago
- Loft rentals Chicago
- Townhouse rentals Chicago
- Family-friendly rentals Chicago
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Rentals with a sauna Chicago
- Rentals with a fireplace Chicago
- Rentals with an EV charger Chicago
- Rentals with pools Chicago
- Apartment rentals Chicago
- Hotel rooms Chicago
- Pet-friendly rentals Chicago
- Rentals with a home theater Chicago
- Rentals with outdoor seating Chicago
- Boutique hotels Chicago
- Rentals with a balcony Chicago
- Rentals with beach access Chicago
- Luxury rentals Chicago
- Mansion rentals Chicago
- Lake house rentals Chicago
- Rentals with lake access Chicago
- Smoking-friendly rentals Chicago
- Condo rentals Chicago
- Rentals with a hot tub Chicago
- Waterfront rentals Chicago
- Guesthouse rentals Chicago
- Private suite rentals Chicago
- Fitness-friendly rentals Chicago
- Beachfront rentals Chicago
- House rentals Chicago
- Rentals with a washer and dryer Chicago
- Serviced apartment 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
- Soldier Field
- 875 North Michigan Avenue
- The Field Museum
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Union Park
- University of Chicago
- Lincoln Park Zoo
- Chicago River Walk
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory
- Washington Park Zoo
- Loyola University Chicago
- Indiana Dunes State Park
- Oak Street Beach
- Illinois Beach State Park
- Things to do Chicago
- Sightseeing Chicago
- Sports activities Chicago
- Art and culture Chicago
- Food and drink Chicago
- Tours Chicago
- Nature and outdoors Chicago
- Things to do Cook County
- Sports activities Cook County
- Tours Cook County
- Nature and outdoors Cook County
- Art and culture Cook County
- Sightseeing Cook County
- Food and drink Cook County
- Things to do Illinois
- Sightseeing Illinois
- Art and culture Illinois
- Tours Illinois
- Food and drink Illinois
- Nature and outdoors Illinois
- Sports activities Illinois
- Things to do United States
- Food and drink United States
- Entertainment United States
- Wellness United States
- Sightseeing United States
- Sports activities United States
- Nature and outdoors United States
- Tours United States
- Art and culture United States







