Adventure Sport Hotels & Resorts in South Side from AU$221
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on South Side Adventure Sport Hotels
Our top choices for South Side adventure hotels
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHGBedford Park
9.0 out of 10, Wonderful, (1,326 reviews)
"Excellent place to stay at perfect location and breakfast was also amazing "
Priyank
The price is AU$269
includes taxes & fees
15 June - 16 June
8.6 out of 10, Excellent, (90 reviews)
"The stay was great, everyday the place is cleaned. And the location of the guest is close to the Mariano's grocery store."
Stefano
The price is AU$221
includes taxes & fees
28 May - 29 May
Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
Comfortable 3BR Getaway w/ Bonus Attic Lounge to RelaxCalumet Park
10.0 out of 10, Exceptional, (6 reviews)
"Lakeia was very accommodating throughout our stay."
Timothy K.
The price is AU$353
includes taxes & fees
9 June - 10 June
ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown ChicagoKenwood
10.0 out of 10, Exceptional, (2 reviews)
"Exactly as described, would recommend"
Anonymous traveller
The price is AU$694
includes taxes & fees
28 May - 29 May
8.2 out of 10, Very good, (2,729 reviews)
"Amazing place"
Rodolfo
The price is AU$287
includes taxes & fees
2 June - 3 June
8.8 out of 10, Excellent, (1,277 reviews)
"Happy with our stay!"
Jennifer
The price is AU$316
includes taxes & fees
17 June - 18 June
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Sonesta ES Suites Chicago Downtown Magnificent Mile - MedicalDowntown Chicago
8.6 out of 10, Excellent, (2,469 reviews)
"Perfect location, very comfortable rooms, friendly staff."
Annabelle
The price is AU$380
includes taxes & fees
14 June - 15 June
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top South Side Hotel Reviews
Carlton Inn Midway
4/10 Poor
Explore a world of travel with Expedia
- Hotels near Auditorium Building and Theatre
- Avalon Park Hotels
- Brighton Park Hotels
- Hotels near Buckingham Fountain
- Central Station Hotels
- Hotels near Chicago 59th Street Station
- Apartments in Chicago 63rd Street Station
- B&B in Chicago Halsted Station
- All Inclusive Hotels in Chicago
- Business Hotels in Chicago
- Casino Hotels in Chicago
- Cheap Hotels in Chicago
- Luxury Hotels in Chicago
- Spa Hotels in Chicago
- Chicago Hotels
- Boutique Hotels in Chicago Lawn
- Family Hotels in Chicago Lawn
- Historic Hotels in Chicago Lawn
- Hotels with Pool in Chicago Lawn
- Romantic Hotels in Chicago Lawn
- Hotels near Chicago McCormick Place Station
- Inns in Chicago McCormick Place Station
- Hotels near Chicago Museum Campus-11th Street Station
- Business Hotels in Chicago Museum Campus
- Cheap Hotels in Chicago Museum Campus
- Historic Hotels in Chicago Museum Campus
- Hotels near Chicago South Shore Station
- Chinatown Hotels
- Hotels near Damen Station
- Downtown Chicago Hotels
- Boutique Hotels in Englewood
- Englewood Hotels
- Cheap Hotels in Essex
- Family Hotels in Essex
- Hotels near Field Museum of Natural History
- Fuller Park Hotels
- Four Seasons Hotels in Gold Coast
- Grace Abbott Homes Hotels
- Hotels near Grant Park
- Greater Grand Crossing Hotels
- Hotels near Halsted Station
- Boutique Hotels in Hyde Park
- Cheap Hotels in Hyde Park
- Green Hotels in Hyde Park
- Luxury Hotels in Hyde Park
- Spa Hotels in Hyde Park
- Hyde Park Hotels
- Hotels near Hyde Park Hair Salon
- Hotels near Illinois Institute of Technology
- Hotels near Jackson Park
- Hotels near Lakefront Trail
- Cheap Hotels in Little Italy
- Little Italy Hotels
- Hotels near Lollapalooza
- Lower West Side Hotels
- Hotels near McCormick Place
- Lgbt Welcoming Hotels in Near South Side
- Near South Side Hotels
- Luxury Hotels in Oakland
- Cheap Hotels in Pilsen
- Printers Row Hotels
- Hotels near Roosevelt University
- Hotels near SR Crown Hall
- Hotels near Soldier Field
- Boutique Hotels in South Chicago
- Historic Hotels in South Chicago
- Spa Hotels in South Chicago
- South Loop Hotels
- South Shore Hotels
- Hotels near University of Chicago
- Boutique Hotels in Washington Park
- Washington Park Hotels
- West Englewood Hotels
- Buckingham Fountain
- Visit Brighton Park
- Visit Canaryville
- Visit Grace Abbott Homes
- Visit Grand Boulevard
- Visit Jackson Park Highlands
- Chicago Museum of Science and Industry
- Visit South Loop
- Chicago Holidays
- Grace Abbott Homes Holidays
- Grant Park
- Greater Salem Baptist Church
- Hyde Park Hair Salon
- Robie House
- South Loop Holidays
- University of Illinois Chicago