
Bed and breakfast holiday rentals in Chicago
Find and book unique bed & 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 3
Room 3 Features: King bed In-suite bath Flat-screen television w/ free cable Wireless internet Ceiling Fan Alarm clock Bathrobes All Rooms include Central Heat/ Air Conditioning This room is special because it features a large steam room and shower combination - your own private spa. The room is located at the center of the property adjacent to our common area kitchen. * 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.) 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).

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

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."

#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 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.

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.
Popular amenities for bed & breakfast rentals in Chicago
Family-friendly bed & breakfast rentals

Villa Dubois Guest House Room 3

Private bedroom with shared bath

Great Edgewater/Andersonville private suite

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

Top location, sunny UofC Prof on campus home
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

Large private room w/ shared bathroom in Boystown!

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

Peaceful King Room in Boutique Wicker Park B&B
Other bed and breakfast holiday rentals

Historic campus U of C Prof. mansion, top location

Private bedroom with shared bath

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

Great Edgewater/Andersonville private suite

Urban Oasis Pilsen - guest room in townhouse

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

Lovely UofC Prof mansion great on campus location

(BR#1) Welcoming, warm & comfortable, 3 guests
When is the best time to visit Chicago?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $87 SGD | $104 SGD | $100 SGD | $117 SGD | $139 SGD | $156 SGD | $153 SGD | $168 SGD | $147 SGD | $135 SGD | $120 SGD | $111 SGD |
| 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 holiday rentals
Explore 70 holiday rentals in Chicago

Nightly prices starting at
Chicago holiday rentals start at $39 SGD per night before taxes and fees

Verified guest reviews
Over 5,550 verified reviews to help you choose

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
70 of Chicago holiday 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
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