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Bed and breakfast holiday 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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A spacious room features a king bed adorned with a decorative duvet and colorful accent pillows. Natural light enters through a window, illuminating the wood floors. A ceiling fan is installed, and a small rug is placed at the foot of the bed, contributing to the room's comfort.
Private room in Edgewater
5 out of 5 average rating, 9 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, 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
Guest suite in Lake Zurich
4.9 out of 5 average rating, 52 reviews

Private Guest Suite • Sleeps 4 • Separate Entrance

⭐ Private walkout entrance ⭐ 1000 sq ft private guest suite ⭐ Fenced backyard + patio + fire pit ⭐ Pet friendly ⭐ Free driveway parking Welcome to beautiful Lake Zurich! This 1000 sqft walkout awaits you. The fenced yard makes it a pleasure to welcome your furry family members too. Whether you are here for an adventure or business, a couple, family, or a group of friends -please enjoy your stay! ✨ Our space is best suited for guests looking for a comfortable, quiet, and relaxing stay!

Guest favourite
Private room in Wilmette
4.95 out of 5 average rating, 284 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.) A lovely and spacious bedroom in our home. 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. Meaningful conversation (if you want it).

Top Guest favourite
Private room in Edgewater
4.96 out of 5 average rating, 292 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

Superhost
Private room in Lake View
4.64 out of 5 average rating, 14 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
4.79 out of 5 average rating, 368 reviews

British Themed 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

Superhost
Private room in Edgewater
4.82 out of 5 average rating, 405 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, 378 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
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, 180 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.

A spacious bedroom features a queen bed with a dark quilt and two decorative pillows. Natural light streams in through two windows, revealing a neutral color palette and patterned wallpaper. A minimalist shelf and a wooden chair complete the room's inviting design.
Private room in Wrigleyville
4.67 out of 5 average rating, 39 reviews

Wrigleyville Suites Room 1

Wrigleyville Suites are 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 Cubs Stadium. Room 1 is a private room with a queen bed and shared bathroom for up to 2 guests. It is one of our largest and brightest room.

Guest favourite
Private room in Norwood Park
4.77 out of 5 average rating, 341 reviews

Chicago River Room, near 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.

Popular amenities for Chicago bed and breakfasts

When is the best time to visit Chicago?

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Avg. price$99 AUD$118 AUD$113 AUD$132 AUD$157 AUD$176 AUD$173 AUD$190 AUD$166 AUD$157 AUD$155 AUD$142 AUD
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Quick stats about bed and breakfast rentals in Chicago

  • Total holiday rentals

    Explore 70 holiday rentals in Chicago

  • Nightly prices starting at

    Chicago holiday rentals start at $44 AUD per night before taxes and fees

  • Verified guest reviews

    Over 5,550 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Chicago holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chicago rentals

  • 4.7 Average rating

    Chicago stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    Chicago's top spots, include Millennium Park, Wrigley Field, and Lincoln Park

Destinations to explore

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