
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.

House 5863 Bed and Breakfast Room 2
Room 2 Features: Queen bed Private bath [Bath is located across the hall from the guest room] Flat-screen television w/ free cable Wireless internet Ceiling Fan Alarm clock Bathrobes All Rooms include Central Heat/ Air Conditioning This room offers quiet comfort and value. We have discounted the price only because the bath, although private, is located across the hall from the guest room. The room is located at the center of the house and is very quiet. * All guests must be fully vaccinated for Covid-19 and at least 2 weeks after 2nd shot. * City of Chicago Bed and Breakfast License Number #2207267

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

(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.) 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. Really friendly small Yorkie-poo dog in the home. Meaningful conversation (if you want it).

Country Retreat, 2 Block walk to Metra Train
Country farmhouse, 2 block walk to Metra train--45 minutes to Chicago and all city has to offer! Park and trails across the street; bike, run, hike, fly fish, kayak, and horse back riding nearby. Relax and watch sunset from our cozy wrap around porch! We are just a few miles from Wheaton College, walk to train and you can get there in 2 train stops or a quick drive. Other points of interest in the area are Cantigny Park just 1 mile away and Central DuPage hospital is a 2 block walk into town.

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, TV den, and balcony.

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

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

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."

#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.

Chicago River Room near Resurrection Med Ctr
R+ My other listings can be found through my profile page. 7 minutes to O'Hare Airport See below for details. Highway entrance 1 block away, so you can easily drive anywhere. Walking distance to pharmacy, shopping mall (including grocery store), health club, train station, restaurants and a library. 0.6 miles to Harlem Blue Line. Prices are subject to change.

Dubois Guest House Room 102
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 102 is a private room with shared bathroom for up to 2 guests.
Popular amenities for Chicago bed and breakfast rentals
Family-friendly bed and breakfast rentals

Great Edgewater/Andersonville private suite

Urban Oasis Pilsen - guest room in townhouse

Cloudgate Room, minutes to O'Hare in Safest Area

Chicago River Room near Resurrection Med Ctr

Lovely UofC Prof mansion great on campus location

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

Peaceful King Room in Boutique Wicker Park B&B

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

Romantic Queen Room in Boutique Wicker Park B&B

Historic campus U of C Prof. mansion, top location

Historic campus house owned by U of C Prof

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

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

Cloudgate Room, minutes to O'Hare in Safest Area

Romantic King Room in Boutique Wicker Park B&B

Luxurious King Room in Boutique Wicker Park B&B
Other bed and breakfast vacation rentals

Historic campus U of C Prof. mansion, top location

Great Edgewater/Andersonville private suite

Urban Oasis Pilsen - guest room in townhouse

Cloudgate Room, minutes to O'Hare in Safest Area

Chicago River Room near Resurrection Med Ctr

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 | R1,165 ZAR | R1,388 ZAR | R1,336 ZAR | R1,559 ZAR | R1,850 ZAR | R2,073 ZAR | R2,038 ZAR | R2,244 ZAR | R1,953 ZAR | R1,799 ZAR | R1,593 ZAR | R1,473 ZAR |
| 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 60 vacation rentals in Chicago

Nightly prices starting at
Chicago vacation rentals start at R685 ZAR per night before taxes and fees

Verified guest reviews
Over 5,230 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
60 of Chicago vacation rentals include wi-fi access

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

4.6 Average rating
Chicago stays receive an average rating of 4.6 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
- Downtown Chicago Vacation rentals
- Indianapolis Vacation rentals
- Southern Indiana Vacation rentals
- Detroit Vacation rentals
- St. Louis Vacation rentals
- Columbus Vacation rentals
- Louisville Vacation rentals
- Cincinnati Vacation rentals
- Wisconsin River Vacation rentals
- Milwaukee Vacation rentals
- Windsor Vacation rentals
- Rentals with a sauna Chicago
- Rentals with a home theater Chicago
- Rentals with outdoor seating Chicago
- Loft rentals Chicago
- Lakehouse rentals Chicago
- Family-friendly rentals Chicago
- Rentals with an EV charger Chicago
- Rentals with an accessible height bed Chicago
- Rentals with breakfast Chicago
- Rentals with a fire pit Chicago
- Private suite rentals Chicago
- Rentals with a balcony Chicago
- Rentals with a fireplace Chicago
- Smoking-friendly rentals Chicago
- Fitness-friendly rentals Chicago
- Luxury rentals Chicago
- Beachfront rentals Chicago
- Rentals with a patio Chicago
- Rentals with lake access Chicago
- Boutique hotels Chicago
- Condo rentals Chicago
- Rentals with a hot tub Chicago
- Rentals with pools Chicago
- Serviced apartment rentals Chicago
- Pet-friendly rentals Chicago
- Waterfront rentals Chicago
- Guesthouse rentals Chicago
- House rentals Chicago
- Townhouse rentals Chicago
- Apartment rentals Chicago
- Rentals with beach access Chicago
- Rentals with a washer and dryer Chicago
- Mansion rentals Chicago
- Bed and breakfasts Cook County
- Bed and breakfasts Illinois
- Bed and breakfasts United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Lincoln Park Zoo
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- The Beverly Country Club
- Willis Tower
- Illinois Beach State Park
- Washington Park Zoo
- The 606
- Raging Waves Waterpark
- Things to do Chicago
- Food and drink Chicago
- Sightseeing Chicago
- Sports activities Chicago
- Nature and outdoors Chicago
- Tours Chicago
- Entertainment Chicago
- Art and culture Chicago
- Things to do Cook County
- Sports activities Cook County
- Tours Cook County
- Food and drink Cook County
- Entertainment Cook County
- Sightseeing Cook County
- Art and culture Cook County
- Nature and outdoors Cook County
- Things to do Illinois
- Food and drink Illinois
- Nature and outdoors Illinois
- Art and culture Illinois
- Tours Illinois
- Sports activities Illinois
- Sightseeing Illinois
- Things to do United States
- Sightseeing United States
- Tours United States
- Wellness United States
- Entertainment United States
- Art and culture United States
- Food and drink United States
- Sports activities United States
- Nature and outdoors United States






