Bed and breakfast vacation rentals in South Side

Find and book unique bed and breakfast rentals on Airbnb

Top-rated bed and breakfast rentals in South Side

Guests agree: these bed and breakfast rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

Private room in Chicago

4.99 out of 5 average rating, 112 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 favorite

A comfortable seating area is highlighted by a wooden rocking chair draped with a red throw. A small side table holds books, while light-colored walls and a vibrant rug contribute to a cozy ambiance. Stairs lead to the upper level, adding architectural interest.

Private room in Wilmette

4.95 out of 5 average rating, 255 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 Chicago

4.83 out of 5 average rating, 378 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

Loft in Chicago

4.81 out of 5 average rating, 27 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: • Steps to Jackson Park Hospital • 22-min Metra train ride to downtown • 15-min drive downtown • 11-min drive to Obama Presidential Center, Museum of Science & Industry, UChicago, Hyde Park, Jackson Park Highlands & Golf Course • In close proximity to Lake Shore Drive, Starbucks, market, laundromat, fast food • Free breakfast • Easy parking

A well-lit bathroom features a classic pedestal sink with a large mirror above. The walls are adorned with light-colored wainscoting and a floral print artwork. A towel is neatly hung, and a window with soft curtains allows natural light to brighten the space.

Private room in Winfield

4.95 out of 5 average rating, 62 reviews

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 guest favorite

A spacious balcony features a black metal table surrounded by two red chairs and a small seating area. A grill is positioned against the wall, and patterned outdoor rugs cover the floor. Overhead, string lights enhance the inviting atmosphere.

Private room in Chicago

5 out of 5 average rating, 120 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 favorite

A living area features a black leather sofa adorned with orange accent pillows. A wooden coffee table displays decorative items and candles. Large windows allow natural light to fill the space, surrounded by lush green plants and a striking wall art piece of a face.

Private room in Chicago

4.95 out of 5 average rating, 262 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

Top guest favorite

Private room in Evanston

4.97 out of 5 average rating, 579 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)

A living area is visible through an open doorway, featuring a comfortable sofa and two accent chairs. Natural light enters through large windows, illuminating a decorative area rug on hardwood floors. A small dining table with modern chairs is positioned in the foreground.

Private room in Chicago

4.83 out of 5 average rating, 6 reviews

Four bedroom apartment

Located in the middle of Chicago's Iconic Boystown in the Lakeview neighborhood, this four bedroom (2 queen beds, 2 full) two bathroom can sleep eight people in the four rooms and two people on a pull out sofa. There is a full kitchen, small washer and dryer, wifi, and a couple of small eating areas. This room is on the third floor and does not have an elevator. Continental breakfast is included at the neighboring property. Please note some rooms can be loud due to street noise.

Superhost

A city skyline is illuminated at dusk, showcasing tall buildings and a prominent river on the left side. The streets are lined with light, creating a vibrant atmosphere as the city transitions into night.

Private room in Chicago

4.81 out of 5 average rating, 353 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

Guest favorite

A decorative ceramic piece in shades of blue with a brown handle rests on a dark surface. It is positioned near a bowl filled with colorful, glittery ornaments and a vase featuring a patterned design. The arrangement adds an artistic touch to the space.

Private room in Chicago

4.91 out of 5 average rating, 351 reviews

SuperHost with Private bedroom/bath/entry Lakeview

Fun, vibrant residential neighborhood surrounded by bars, theaters, coffee shops, restaurants and boutiques. Private access for one 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."

A modern kitchen is featured with stainless steel appliances, including a gas stove and oven. Ample cabinetry offers storage space, complemented by a light granite countertop. A large window allows natural light to brighten the area, while stylish pendant lighting hangs overhead.

Private room in Chicago

4.9 out of 5 average rating, 21 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.