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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Private room in Edgewater
4.71 out of 5 average rating, 28 reviews

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

Top guest favorite
Private room in Hyde Park
4.99 out of 5 average rating, 121 reviews

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

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).

Private room in Winfield
4.95 out of 5 average rating, 62 reviews

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.

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
4.84 out of 5 average rating, 374 reviews

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

Guest favorite
Private room in Chicago
4.82 out of 5 average rating, 385 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.

A spacious bedroom features a patterned blue accent wall and a wooden artwork above the bed. A comfortable bed is dressed in neutral linens, flanked by two bedside tables with reading lamps. A ceiling fan and natural light from a window enhance the inviting ambiance.
Private room in Bronzeville
4.83 out of 5 average rating, 40 reviews

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

When is the best time to visit Chicago?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR1,165 ZARR1,388 ZARR1,336 ZARR1,559 ZARR1,850 ZARR2,073 ZARR2,038 ZARR2,244 ZARR1,953 ZARR1,799 ZARR1,593 ZARR1,473 ZAR
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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 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

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