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 in East Pilsen

5 out of 5 average rating, 94 reviews

Urban Oasis Pilsen - guest room in townhouse

A walk-up in one of Chicago's coolest neighborhood - Pilsen! Your private bedroom has a queen-size bed & an en-suite bathroom with a tub/shower combo. There is a small desk, ample storage space, and a TV with streaming services. While your many triple-paned windows let in light, air, and sunshine, you will also hear the I-90/94 near us. Please note that your room is on the third floor of the building (40 steps). On the second floor, you'll find (y)our kitchen, living rooms, TV den, and balcony.

Guest favourite

Private room in Wilmette

4.95 out of 5 average rating, 242 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).

Superhost

Place to stay in South Shore

4.81 out of 5 average rating, 27 reviews

Historic Basement W/Parking near Metra & Hyde Park

Stay like a local! Experience a historic XIXth Century's basement at this iconic African American district, within a 15-min drive downtown, 5-min drive to Hyde Park, the Obama Center, Museum of Science and Industry, and Jackson Park golf course. Steps to Stony Island Metra Station for a 22-min rail-train ride to downtown via University of Chicago, McCormick Place, Grant Park, Millennium Park. A stone's throw away from Lake Shore Drive, Starbucks, groceries, laundromat, food. Free onsite parking.

Guest favourite

Private room in Hyde Park

4.95 out of 5 average rating, 111 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

Guest favourite

Private room in Irving Park

4.91 out of 5 average rating, 104 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 in Andersonville

4.95 out of 5 average rating, 234 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

Guest favourite

Private room in Evanston

4.97 out of 5 average rating, 555 reviews

Classy and Cozy home in Evanston

Come to our classy, tastefully decorated home. You will be close to downtown Evanston, Northwestern University, Chicago, and environs. Your private room provides great comfort for two. We are Covid-19 compliant and fully vaccinated. PLEASE NOTICE: The bathroom is not for sharing, it’s attached to the bedroom and it has a jacuzzi. A nice breakfast is provided every morning with fresh fruit, homemade bread, coffee/tea and eggs/potatoes or pancakes. We also can provide an extra bed ($25)

Private room in Evanston

4.63 out of 5 average rating, 89 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 in East Rogers Park

4.81 out of 5 average rating, 329 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

Guest favourite

Private room in Lake View

4.9 out of 5 average rating, 336 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."

Private room in Norwood Park

4.76 out of 5 average rating, 307 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

4.89 out of 5 average rating, 57 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.