
Bed and breakfast holiday rentals in South Side
Find and book unique bed and breakfasts on Airbnb
Top-rated bed and breakfasts in South Side
Guests agree: These bed and breakfast rentals are highly rated for location, cleanliness and more.

House 5863 Bed and Breakfast Room 3
Room 3 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 room is special because it features a large steam room and shower combination - your own private spa. The room is located at the center of the property adjacent to our common area kitchen. * 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

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

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

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

(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).

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

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, and balcony.

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.

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

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."

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.

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 South Side bed and breakfasts
Family-Friendly Bed and Breakfasts

Private room with private entrance in Boystown

Bright Room with a Garden View

Great Edgewater/Andersonville private suite

Large private room w/ shared bathroom in Boystown!

Urban Oasis Pilsen - guest room in townhouse

Lovely UofC Prof mansion great on campus location

Cozy Garden Room in the middle of Boystown!

(BR#1) Welcoming, warm & comfortable, 3 guests
Bed and breakfast rentals with breakfast

Cute room in downtown Boystown

Private room with private entrance in Boystown

Historic campus U of C Prof. mansion, top location

Queen Bed with Private Bathroom in Boystown

Historic campus house owned by U of C Prof

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

Luxurious King Room in Boutique Wicker Park B&B

Cozy Garden Room in the middle of Boystown!
Other bed and breakfast holiday rentals

Private room with private entrance in Boystown

Bright Room with a Garden View

Great Edgewater/Andersonville private suite

Large private room w/ shared bathroom in Boystown!

Urban Oasis Pilsen - guest room in townhouse

Lovely UofC Prof mansion great on campus location

Cozy Garden Room in the middle of Boystown!

(BR#1) Welcoming, warm & comfortable, 3 guests
Destinations to explore
- Chicagoย Holiday rentals
- Plattevilleย Holiday rentals
- Indianapolisย Holiday rentals
- Downtown Chicagoย Holiday rentals
- Louisvilleย Holiday rentals
- Detroitย Holiday rentals
- Southern Indianaย Holiday rentals
- Columbusย Holiday rentals
- St. Louisย Holiday rentals
- Cincinnatiย Holiday rentals
- Wisconsin Riverย Holiday rentals
- Milwaukeeย Holiday rentals
- Rentals with beach accessย South Side
- Apartment rentalsย South Side
- Rentals with lake accessย South Side
- Rentals with a fire pitย South Side
- Family-friendly rentalsย South Side
- Rentals with poolsย South Side
- Rentals with breakfastย South Side
- Smoking-friendly rentalsย South Side
- House rentalsย South Side
- Rentals with a patioย South Side
- Townhouse rentalsย South Side
- Rentals with an EV chargerย South Side
- Rentals with a fireplaceย South Side
- Waterfront rentalsย South Side
- Rentals with a washing machine and dryerย South Side
- Private suite rentalsย South Side
- Fitness-friendly rentalsย South Side
- Rentals with a hot tubย South Side
- Rentals with outdoor seatingย South Side
- Pet-friendly rentalsย South Side
- Condo rentalsย South Side
- Bed and breakfastsย Chicago
- Bed and breakfastsย Cook County
- Bed and breakfastsย Illinois
- Bed and breakfastsย United States
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Union Park
- Lincoln Park Zoo
- University of Chicago
- Brookfield Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- Museum of Science and Industry
- Illinois Beach State Park
- Willis Tower




