Bed and breakfast vacation rentals in South Side

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Top-rated bed and breakfast rentals in South Side

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A brick building with large windows is surrounded by lush greenery. The structure features multiple stories and a prominent entrance. The façade reflects a blend of contemporary and classic architectural elements, with trees providing natural shade and enhancing the inviting exterior.

Private room in Chicago

4.82 out of 5 average rating, 28 reviews

House 5863 Bed and Breakfast Room 1

Room 1 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 This is the owner's favorite room as it has a large bay window that overlooks the park across the street from the bed & breakfast. The room is adjacent to the common living area. * 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 favorite

A spacious living area is highlighted by large windows that invite natural light, revealing a chandelier above and a decorative mirror on the wall. Comfortable seating arrangements include white sofas and a glass coffee table. A bouquet of flowers adds a touch of elegance to the room.

Private room in Chicago

4.99 out of 5 average rating, 109 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).

The charming entrance features a set of stairs leading to a covered porch, flanked by potted plants. Two rocking chairs are positioned invitingly beside the front door, while pumpkins are decoratively placed on the steps, enhancing the welcoming atmosphere.

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 three-story residential building is presented, featuring a combination of textured stone and smooth brick facades. Large windows allow natural light to illuminate the interior spaces. A small staircase leads to a front door, framed by two large windows. A decorative plant is placed by the entrance.

Private room in Chicago

5 out of 5 average rating, 113 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

The kitchen features wooden cabinetry with glass display shelves showcasing colorful dishware. Recessed lighting highlights the workspace, while a kitchen island with a sink and bar stool offers additional seating. A dark stone floor adds texture, complementing the exposed brick and modern appliances.

Private room in Chicago

4.95 out of 5 average rating, 257 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

A modern walk-in shower features a seamless glass enclosure and neutral-toned tiled walls. Safety grab bars are installed for support, while a handheld showerhead and body wash dispensers are available for convenience. The shower floor is designed with textured tiles for stability.

Private room in Chicago

4.8 out of 5 average rating, 5 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.

A charming garden pathway leads to a two-story building framed by a large tree and greenery. Lush plants and shrubs line the path, enhancing the serene ambiance of the outdoor space. The inviting facade of the home features a covered porch adorned with railings.

Private room in Chicago

4.85 out of 5 average rating, 355 reviews

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

Guest favorite

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, 345 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 favorite

A wet bar area includes a combination of modern appliances such as a coffee maker, wine cooler, and mini fridge, all set against a textured backsplash. Ample counter space is provided for meal preparation, with neatly arranged dishes and utensils visible nearby.

Private room in Chicago

4.9 out of 5 average rating, 346 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."

A spacious living and dining area is highlighted by a round wooden table surrounded by four brown chairs. A modern chandelier hangs from the ceiling, and natural light filters through large windows. A cozy seating area includes a blue sofa facing a fireplace and wall-mounted television.

Private room in Chicago

4.9 out of 5 average rating, 20 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.

Guest favorite

A close-up view of a digital keypad lock is displayed, featuring illuminated blue numbers from 0 to 9. The sleek design is highlighted by a shiny silver finish, and a keyhole is visible below the keypad.

Private room in Chicago

4.77 out of 5 average rating, 318 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.