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.

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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

Top guest favourite

Private room in Hyde Park

4.99 out of 5 average rating, 118 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 favourite

Private room in Wilmette

4.94 out of 5 average rating, 262 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 Lake View

4.83 out of 5 average rating, 383 reviews

Bright Room with a Garden View

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. Shares bathroom with 2 rooms Room service and Cubs Game and Concert Day Specials provided to our guest next door at Big Gay Sal's

Top guest favourite

Private room in East Pilsen

5 out of 5 average rating, 128 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 Andersonville

4.95 out of 5 average rating, 278 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

Loft in South Shore

4.83 out of 5 average rating, 29 reviews

Historical Basement by Jackson Park; Metra/Parking

Stay in our historical XIX Century home in Chicago's iconic African American district! Imagine living like locals in this up-and-coming neighborhood. Enjoy: • Proximity to Hyde Park, Lake Shore Drive, Starbucks, market, laundromat, fast food • Steps to Jackson Park Hospital • 22-min Metra train ride to downtown • 15-min drive downtown • Close to Obama Presidential Center, Museum of Science & Industry, UChicago, Jackson Park Highlands & Golf Course • Free designated parking

Guest favourite

Private room in East Rogers Park

4.81 out of 5 average rating, 360 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

Private room in Lake View

4.91 out of 5 average rating, 365 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 favourite

Private room in Norwood Park

4.77 out of 5 average rating, 325 reviews

Chicago River Room near USMLE

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.

Guest favourite

Hotel room in Wicker Park

4.91 out of 5 average rating, 79 reviews

King Room in Boutique Wicker Park B&B

Modern guest room located on the main floor just a block away from great dining, vintage and boutique shopping, art galleries, cool cafes and vibrant nightlife. The Ellen 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.

Private room in Bronzeville

4.86 out of 5 average rating, 35 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.