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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Guest favourite

Private room

4.99 out of 5 average rating, 107 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

4.94 out of 5 average rating, 248 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).

Guest favourite

Private room

4.88 out of 5 average rating, 108 reviews

Serene place with the garden. Free parking.

I live in Albany Park, Chicago. It's quiet, family oriented, with lots of parks and treelined streets. The Chicago River Trail is within walking distance too. My home is a charming 2 flat building, built in 1909. It has lots of original, unique details. My home is a tranquil and peaceful place. My decor mainly consists of hand-made furniture, artwork, wind chimes, etc. I don't use any chemical cleaning supplies, I use only home-made products and essential oils and UV lamp for sanitizing.

Guest favourite

Private room

5 out of 5 average rating, 104 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.

Guest favourite

Private room

4.95 out of 5 average rating, 248 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

4.57 out of 5 average rating, 98 reviews

Gorgeous 1 Bed (King) with Private Bathroom

You’ll love the stylish decor of this charming place to stay. Private in suite full Bathroom. 1 Kingsize bed and 1 XL Futon. Working / computer table with walking closet. Just 1.5-2 miles from Downtown Evanston and Northwestern University, you are a straight shot from countless dining, shopping, & entertainment options. Close to Downtown Chicago. Bus station is on walking distance which will connects you all around Chicago. Beaches are about 3.5 miles. Free Breakfast and Wi-Fi.

Superhost

Private room

4.81 out of 5 average rating, 343 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, Yoga, Gym, Movie Theater, Multiple Bars & Diverse Cuisine within 5-15 min walking

Private room

4.8 out of 5 average rating, 172 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.

Guest favourite

Private room

4.9 out of 5 average rating, 345 reviews

SuperHost with Private bedroom/bath/entry Lakeview

Fun, vibrant residential neighborhood surrounded by bars, theaters, coffee shops, restaurants and boutiques. Private access, use of entire level including 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."

Superhost

Private room

4.88 out of 5 average rating, 16 reviews

Villa Dubois Guest House Room 1

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 1 is a private room with shared bathroom for up to 2 guests. It is one of our largest and brightest room.

Superhost

Private room

4.77 out of 5 average rating, 311 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.

Superhost

Private room

4.5 out of 5 average rating, 6 reviews

Green Room in Dorothys BNB

Located in the middle of Chicago's iconic Boystown in Lakeview, this room has a full bed and two shared bathrooms in a third floor walkup of Dorothy's, . Wifi, continental breakfast, central ac and heat. There are 3 other rooms on the floor. Shared kitchen, living room, washer and dryer. No parking on site, street parking only.