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.

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Private room in Edgewater
5 out of 5 average rating, 15 reviews

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

Top guest favourite
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

Top guest favourite
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 favourite
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 favourite
Private room in South Loop
5 out of 5 average rating, 138 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 favourite
Private room in Edgewater
4.95 out of 5 average rating, 286 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
4.44 out of 5 average rating, 9 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, 364 reviews

Cozy Garden Room in the middle of 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 favourite
Private room in Chicago
4.82 out of 5 average rating, 382 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 favourite
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."

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
4.85 out of 5 average rating, 39 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.

Top guest favourite
Private room in Evanston
4.95 out of 5 average rating, 522 reviews

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.

Popular amenities for Chicago bed and breakfasts

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Avg. price$95 CAD$113 CAD$109 CAD$127 CAD$151 CAD$169 CAD$166 CAD$183 CAD$159 CAD$147 CAD$130 CAD$120 CAD
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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 $56 CAD 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

  • Wifi availability

    60 of Chicago vacation rentals include wifi 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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