A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.

South Side Hotel Guide - Adventure Sport Hotels in South Side, Chicago

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Check availability on South Side Adventure Sport Hotels

Tonight
30 Aug - 31 Aug
Tomorrow
31 Aug - 1 Sept
Next weekend
4 Sept - 6 Sept
In two weeks
11 Sept - 13 Sept

Our top choices for South Side adventure hotels

A hallway with wooden flooring, a dining area with a table and chairs, and a blue sofa.
A room with a wooden herringbone ceiling, a wall clock, and shelves with various decorative items and books.
A neatly made bed with a headboard, two bedside tables with lamps, and a wall-mounted artwork above the bed.
A dining area with a wooden table and chairs, a rock sculpture centerpiece, and a large green wall art piece.

1. Villa Dubois Guest House

Villa Dubois Guest House
Bronzeville
United States
Steven
€130
includes taxes & fees
10 Sept - 11 Sept
Villa Dubois Guest House
A modern living room with a sectional sofa, a TV on a stand, a small dining area, and a door leading to another room.
A modern two-story house with a beige and white facade, a black metal fence, and a small front yard with grass and a potted plant.
A small dining area with a wooden table and matching benches, a candle, and a mug with a rainbow design.
A small dining area with a wooden table and benches, featuring blue plates and a candle holder.

2. Stylish 2BR Near Hyde Park, UChicago & Lake

Stylish 2BR Near Hyde Park, UChicago & Lake
Woodlawn
United States
Brittney J.
€360
includes taxes & fees
31 Aug - 1 Sept
Stylish 2BR Near Hyde Park, UChicago & Lake

3. ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago

ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
Kenwood
United States
Anonymous traveller
€608
includes taxes & fees
14 Sept - 15 Sept
ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
A living room with a blue sectional sofa, a glass coffee table, and yellow curtains.
A bedroom with a bed, a dresser, a mirror, and a wall with 'Blessed' decorations.
A vanity with a mirror, lights, and a vase of flowers.
A flat-screen TV mounted on a wall with a fireplace below it.

4. Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax

Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
Calumet Park
United States
Alisa G.
€238
includes taxes & fees
8 Sept - 9 Sept
Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax

5. Designer Home | Steps to the Obama Center & Beach

Designer Home | Steps to the Obama Center & Beach
Woodlawn
Designer Home | Steps to the Obama Center & Beach
A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.
A modern hotel room with a large window offering a view of the sea and a cityscape. There is a seating area with a sofa and a small table.
A modern bar area with high stools, a bar counter, and shelves of liquor bottles.
A rooftop terrace with a view of a beach and a Ferris wheel, featuring lounge chairs and a colorful mural.

6. The Wade

The Wade
Downtown Chicago
Canada
Ayomikun Jedidiah
€153
includes taxes & fees
31 Aug - 1 Sept
The Wade
A woman descending a set of outdoor stairs in an urban area with tall buildings in the background.
A dining table with a salad, cheese, and wine, surrounded by chairs and a large plant.
A modern bar area with a long counter, multiple bar stools, and a large flat-screen TV.
A spacious lobby with a high ceiling, modern seating, and a central bar area.

7. voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
Downtown Chicago
United States
kaitlyn
€234
includes taxes & fees
7 Sept - 8 Sept
voco Chicago Downtown - Riverwalk by IHG
A modern bar area with a marble countertop, leather bar stools, a chandelier, and a wall-mounted TV.
A modern hotel with a glass facade, multiple floors, and a prominent entrance with a purple-lit canopy.
A hotel room with a large bed, a desk with a lamp, a TV, and a bathroom visible through an open door.
A hotel lobby with a curved floor design, a glass entrance, and a large mural on the wall.

8. Ivy Boutique Hotel

Ivy Boutique Hotel
Downtown Chicago
United States
Melinda
€144
includes taxes & fees
31 Aug - 1 Sept
Ivy Boutique Hotel
An outdoor dining area with tables and umbrellas, overlooking a river with a bridge and high-rise buildings in the background.
A modern hotel room with a large window, a blue sofa, and a lamp.
A spacious lobby with a central bar area, seating, and a large window offering a city view.
A modern bar area with a long counter, multiple bar stools, and a large flat-screen TV.

9. Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG
Downtown Chicago
United States
Victor
€234
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn Chicago Dwtn - The Mart by IHG
A bar area with a counter, menu boards, and a unique seating arrangement with numbered stools.
A reception area with a counter, seating, and lockers.
A two-story building with a sign for 'Chicago Hotel Collection' and 'Coffee Food Drinks' on the facade.
A modern room with bunk beds, a sofa, a round coffee table, and a view of the city through large windows.

10. The Chicago Hotel Collection River North

The Chicago Hotel Collection River North
Downtown Chicago
United States
Eduardo
€112
includes taxes & fees
31 Aug - 1 Sept
The Chicago Hotel Collection River North
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Top South Side Hotel Reviews

Jaslin Hotel

Jaslin Hotel

8/10 Good
"Parking a couple blocks from the property is a little bit difficult for me but was doable in all. No parking in the property so bear that in mind."
Rita 1-night trip
Posted 2 hours ago
Jaslin Hotel
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

10/10 Excellent
"Na"
Marianne 1-night trip
Posted 2 hours ago
Holiday Inn Chicago – Midway Airport S by IHG
Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

10/10 Excellent
"In Hyde Park. Very close to lots of restaurants and a short Uber drive to the Obama Center and Museum of Science and Industry"
India 1-night trip
Posted 5 hours ago
Hyatt Place Chicago-South/University Medical Center
Chicago Marriott Midway

Chicago Marriott Midway

8/10 Good
"The room and lobby were clean. The bathtub was a bit dated but the water pressure and heat were superb!!!! We stayed here since we had a super early flight and took the shuttle to the airport. No complaints."
Shabreka 1-night trip
Posted 1 day ago
Chicago Marriott Midway
Carlton Inn Midway

Carlton Inn Midway

10/10 Excellent
"Good to stay and staff were good"
Rahul Pandit 1-night trip
Posted 5 days ago
Carlton Inn Midway

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