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.

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A spacious room features a king bed adorned with a decorative duvet and colorful accent pillows. Natural light enters through a window, illuminating the wood floors. A ceiling fan is installed, and a small rug is placed at the foot of the bed, contributing to the room's comfort.
Private room in Edgewater
5 out of 5 average rating, 8 reviews

House 5863 Bed and Breakfast Room 4

Room 4 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 Room 4 is our brightest room and has the added benefit of having direct access to our common deck area. The room also features a pull-out sofa and can accommodate an additional guest (Subject to additional charge). * 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

Guest favorite
Private room in Wilmette
4.95 out of 5 average rating, 277 reviews

(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).

Top guest favorite
Private room in Hyde Park
4.95 out of 5 average rating, 135 reviews

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

Top guest favorite
Private room in South Loop
5 out of 5 average rating, 139 reviews

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.

Top guest favorite
Private room in Edgewater
4.95 out of 5 average rating, 287 reviews

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

Private room in Lake View
4.5 out of 5 average rating, 10 reviews

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.

Private room in Lake View
4.76 out of 5 average rating, 321 reviews

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
A modern guest room is presented with a king-size bed dressed in crisp white linens. Unique wall art features a bird motif, complemented by stylish brass sconces. A geometric pendant light hangs above, enhancing the room's contemporary appeal. Framed photos add a personal touch.
Hotel room in Wicker Park
5 out of 5 average rating, 6 reviews

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.

Top guest favorite
Private room in Chicago
4.83 out of 5 average rating, 389 reviews

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

Top guest favorite
A bright family room features large windows allowing natural light to filter in. Two armchairs are positioned near a coffee table stacked with books. An exercise bike is against a wall, and a television is mounted above a fireplace, enhancing the room's functionality.
Private room in Lake View
4.91 out of 5 average rating, 375 reviews

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."

Guest favorite
A spacious living area is observed with a comfortable blue sofa adorned with patterned cushions. A green armchair is positioned nearby. A decorative coffee table with a tray sits on a patterned rug. Light streams in from windows, and the blue wall adds a calming backdrop.
Private room in East Rogers Park
4.81 out of 5 average rating, 176 reviews

#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.

Superhost
Private room in Norwood Park
4.77 out of 5 average rating, 337 reviews

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.

Popular amenities for Chicago bed and breakfast rentals

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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 € 34 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

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