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

Adventure Sport Hotels & Resorts in South Side from NZ$110

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Check availability on South Side Adventure Sport Hotels

Tonight
16 Oct - 17 Oct
Tomorrow
17 Oct - 18 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

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 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.
A modern kitchen with white cabinets, stainless steel appliances, and patterned wallpaper.

1. Villa Dubois Guest House

Villa Dubois Guest House
Bronzeville
United States
Yohannes
NZ$268
includes taxes & fees
4 Nov - 5 Nov
Villa Dubois Guest House
Private kitchen
Living area
Interior
Living area

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

ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
Kenwood
United States
Anonymous traveller
NZ$911
includes taxes & fees
20 Oct - 21 Oct
ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."
A residential street with a sidewalk, houses, and greenery.
A bar area with a checkered floor, wooden chairs, a bar counter, and two televisions mounted on the wall.
A lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.

3. Carleton of Oak Park

Carleton of Oak Park
Oak Park
United States
Brad
NZ$240
includes taxes & fees
27 Oct - 28 Oct
Carleton of Oak Park
An indoor swimming pool with lounge chairs and a stone wall.
A modern living room with a large chandelier, leather sofas, and a round coffee table.
A gym with treadmills, elliptical machines, and a view of an outdoor swimming pool.
A hotel lobby with a reception desk, seating area, and a sign reading "SIP & SAVOR COCKTAILS & EATS".

4. Crowne Plaza Chicago SW - Burr Ridge by IHG

Crowne Plaza Chicago SW - Burr Ridge by IHG
Burr Ridge
United States
Jack
NZ$214
includes taxes & fees
15 Nov - 16 Nov
Crowne Plaza Chicago SW - Burr Ridge by IHG
Room
A spacious lobby with a marble floor, modern lighting fixtures, a seating area with sofas and chairs, and a visible kitchen area in the background.
A glass-enclosed patio with outdoor seating and a view of the surrounding buildings.
A hotel with a sign reading "Chicago Club Inn & Suites" at night.

5. Chicago Club Inn & Suites

Chicago Club Inn & Suites
Westmont
United States
Jonathan
NZ$110
includes taxes & fees
16 Nov - 17 Nov
Chicago Club Inn & Suites
A restaurant interior with a retro 1943 theme, featuring hanging pendant lights, a checkered floor, and a large illuminated 'CHICAGO' sign.
A hotel room with a large bed, two bedside tables with lamps, a wooden headboard, and a carpeted floor.
A hotel room with a kitchenette, a bathroom, a seating area, and a desk.
A hotel lobby with a patterned carpet, a blue sofa, a reception desk, and a sign for the restaurant.

6. Comfort Suites Chicago O'Hare Airport

Comfort Suites Chicago O'Hare Airport
Schiller Park
United States
JIE
NZ$197
includes taxes & fees
1 Nov - 2 Nov
Comfort Suites Chicago O'Hare Airport
A modern hotel with a large glass facade, a covered entrance, and a well-lit parking area.
A modern lounge area with a fireplace, seating, and a bar with red lighting.
A modern lounge area with seating, a fireplace, and large windows.
A modern reception area with a colorful, illuminated reception desk, a seating area with sofas and chairs, and a large screen on the wall.

7. Aloft by Marriott Bolingbrook

Aloft by Marriott Bolingbrook
Bolingbrook
United States
Nelson
NZ$228
includes taxes & fees
1 Nov - 2 Nov
Aloft by Marriott Bolingbrook
A banquet hall with round tables, chairs, and chandeliers.
A hotel room with a large bed, a desk, a chair, a lamp, and a view of trees through the window.
A hotel room with two beds, a desk, a chair, a TV, and a large window with a view of trees.
A gym with treadmills, elliptical machines, and weight stations.

8. Hyatt Lodge Oak Brook Chicago

Hyatt Lodge Oak Brook Chicago
Oak Brook
United States
wayne b
NZ$310
includes taxes & fees
1 Nov - 2 Nov
Hyatt Lodge Oak Brook Chicago
A breakfast setting with a plate of toast, a bowl of fruit, a cup of coffee, and a newspaper on a table by a window with a city view.
A modern interior with a bar area, seating, and large windows offering a city view.
A rooftop pool area with lounge chairs and umbrellas, a city skyline view, and a no diving sign.
A building facade with a dark entrance, two wall-mounted lights, and a sign reading "The Robey Chicago".

9. The Robey, Chicago, a Member of Design Hotels

The Robey, Chicago, a Member of Design Hotels
West Town
United States
Patricia
NZ$467
includes taxes & fees
1 Nov - 2 Nov
The Robey, Chicago, a Member of Design Hotels
A hotel room with two beds, a desk, a TV, and a window with curtains.
A hotel room with two beds, a nightstand, a lamp, and a wooden floor.
A sign for Econo Lodge with a grassy area and trees in the background.
A modern hotel with a prominent sign, multiple balconies, and a parking area.

10. Econo Lodge Willowbrook

Econo Lodge Willowbrook
Willowbrook
United States
Kyle
NZ$121
includes taxes & fees
15 Nov - 16 Nov
Econo Lodge Willowbrook
View all properties

Top South Side Hotel Reviews

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

10/10 Excellent
"Clean and comfortable rooms."
Laura 1-night trip
Posted 5 hours ago
Holiday Inn Chicago – Midway Airport S by IHG
Jaslin Hotel

Jaslin Hotel

10/10 Excellent
"The staff were helpful and friendly. The room was clean upon arrival. Furniture, lamps, etc. were in acceptable condition; I was very pleased. The bathroom and its amenities were great. The bed was firm, but comfortable. The A/C worked very well. The view of the Chicago skyline from the window on the fourth floor was beautiful. There are many great restaurants and shops within walking distance (2-3 block parameter) of the Jaslin. I had lunch at DaiFuku Ramen across the street. Highly recommend! Chinatown is amazing! I hope to visit again in the future. Overall: Very good experience 4.5/5 stars"
Lucas 2-night trip
Posted 9 hours ago
Jaslin Hotel
Chicago Marriott Midway

Chicago Marriott Midway

10/10 Excellent
"Love"
Ananada 3-night trip
Posted 2 days ago
Chicago Marriott Midway

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