
Bed and breakfast holiday rentals in Cook County
Find and book unique bed & breakfast rentals on Airbnb
Top-rated bed and breakfast rentals in Cook County
Guests agree: these bed and breakfast rentals are highly rated for location, cleanliness and more.

(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).

Country Retreat, 2 Block walk to Metra Train
Country farmhouse, 2 block walk to Metra train--45 minutes to Chicago and all city has to offer! Park and trails across the street; bike, run, hike, fly fish, kayak, and horse back riding nearby. Relax and watch sunset from our cozy wrap around porch! We are just a few miles from Wheaton College, walk to train and you can get there in 2 train stops or a quick drive. Other points of interest in the area are Cantigny Park just 1 mile away and Central DuPage hospital is a 2 block walk into town.

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

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.

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

Large private room w/ shared bathroom in 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

The Good Farm: Barn BnB on 44 acres near Lake Mich
Escape to BarnBnB, a charming barn apartment on 44 acres just 15 minutes from Lake Michigan beaches and Indiana Dunes National Park. 🐓🌳 Perfect for families or groups (up to 6 guests), this peaceful retreat blends modern comforts with farm life—free-range chickens, firepit evenings, and trails included. Relax in nature or explore nearby Valparaiso, Chesterton, and Michigan City for the perfect mix of adventure and tranquility.

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

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."

#4 Historic Chicago Home - Private Single Bedroom
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.

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.

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.
Popular amenities for bed & breakfast rentals in Cook County
Family-friendly bed & breakfast rentals

House 5863 Bed and Breakfast Room 3

House 5863 Bed and Breakfast Room 4

5 bedroom sleeps 12 in boystown

Villa Dubois Guest House Room 3

Private bedroom with shared bath

Blue Room in Dorothy's BNB

Four bedroom apartment

House 5863 Bed and Breakfast Room 2
Bed and breakfast rentals with breakfast

Romantic Queen Room in Boutique Wicker Park B&B

Historic campus U of C Prof. mansion, top location

Historic campus house owned by U of C Prof

Sun-Filled King Room in Boutique Wicker Park B&B

Queen Room w/ Balcony in Boutique Wicker Park B&B

Chicago River Room near USMLE

Romantic King Room in Boutique Wicker Park B&B

Lovely UofC Prof mansion great on campus location
Other bed and breakfast holiday rentals

Great Edgewater/Andersonville private suite

Urban Oasis Pilsen - guest room in townhouse

Chicago River Room near USMLE

Cloudgate Room, minutes to O'Hare in Safest Area

Lovely UofC Prof mansion great on campus location

Classy and Cozy home in Evanston

(BR#1) Welcoming, warm & comfortable, 3 guests

SuperHost with Private bedroom/bath/entry Lakeview
Destinations to explore
- Rentals with a washing machine and dryer Cook County
- Townhouse rentals Cook County
- Boutique hotel rentals Cook County
- Villa rentals Cook County
- Ski-in/ski-out rentals Cook County
- Rentals with a balcony Cook County
- Flat rentals Cook County
- Luxury rentals Cook County
- Rentals with an EV charger Cook County
- Waterfront rentals Cook County
- House rentals Cook County
- Rentals with a patio Cook County
- Rentals with an accessible-height toilet Cook County
- Smoking-friendly rentals Cook County
- Beachfront rentals Cook County
- Rentals with outdoor seating Cook County
- Rentals with lake access Cook County
- Pet-friendly rentals Cook County
- Private suite rentals Cook County
- Rentals with a hot tub Cook County
- Fitness-friendly rentals Cook County
- Guest house rentals Cook County
- Rentals with a fireplace Cook County
- Rentals with a firepit Cook County
- Loft rentals Cook County
- Family-friendly rentals Cook County
- Rentals with a cinema Cook County
- Rentals with beach access Cook County
- Rentals with breakfast Cook County
- Apartment rentals Cook County
- Rentals with a kayak Cook County
- Rentals with pools Cook County
- Rentals with an accessible-height bed Cook County
- Rentals with a sauna Cook County
- Bed and breakfasts Illinois
- Bed and breakfasts United States
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- 875 North Michigan Avenue
- Humboldt Park
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Lincoln Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Washington Park Zoo
- Willis Tower
- The Beverly Country Club
- Raging Waves Waterpark
- The 606
- Things to do Cook County
- Art and culture Cook County
- Tours Cook County
- Entertainment Cook County
- Food and drink Cook County
- Sports activities Cook County
- Sightseeing Cook County
- Nature and outdoors Cook County
- Things to do Illinois
- Food and drink Illinois
- Nature and outdoors Illinois
- Tours Illinois
- Art and culture Illinois
- Sightseeing Illinois
- Sports activities Illinois
- Things to do United States
- Sightseeing United States
- Entertainment United States
- Wellness United States
- Tours United States
- Food and drink United States
- Art and culture United States
- Sports activities United States
- Nature and outdoors United States