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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Guest favorite

Private room in Chicago

5 out of 5 average rating, 99 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 freeway I-90/94 near us. 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 room, TV den, and balcony.

Guest favorite

Private room in Wilmette

4.94 out of 5 average rating, 246 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 Evanston

4.69 out of 5 average rating, 74 reviews

Huge (2Beds) 1 Bedroom

Enjoy the glamour of this stylish, upscale place. 2 Beds (Queen+Full) in this bedroom. You’ll love the stylish decor of this charming place to stay. Working / computer table with walking closet. Free Breakfast and Wi-Fi. 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 walking distance which connects you all around Chicago. Beaches are about 3.5 miles

Guest favorite

Private room in Chicago

4.96 out of 5 average rating, 118 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 favorite

Private room in Chicago

4.88 out of 5 average rating, 108 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 favorite

Private room in Chicago

4.95 out of 5 average rating, 242 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

Private room in Chicago

4.85 out of 5 average rating, 324 reviews

Private room with private entrance 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

Superhost

Private room in Evanston

4.84 out of 5 average rating, 126 reviews

Art-filled charm, near NU, transport, shopping

Lovely Tudor art-filled home near Old Orchard, NU, Evanston Hosp., public trans., Pres. Homes & 3 Crowns senior living. Free parking. Private guest bath & shelf in fridge. Suits 1 - 3 guests in main room, or up to 5 in one party if you book both bedrooms. This listing is for ONE ROOM ONLY - to book 2 rooms, go to our other listing, "2 ROOMS FOR UP TO 5, CLOSE TO NU & OLD ORCHARD MALL. Must like dogs. Archie is a friendly lab mix and gets the best reviews of anyone.

Superhost

Private room in Chicago

4.81 out of 5 average rating, 337 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

Private room in Chicago

4.8 out of 5 average rating, 172 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.

Guest favorite

Private room in Chicago

4.9 out of 5 average rating, 344 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."

Superhost

Private room in Chicago

4.77 out of 5 average rating, 311 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.