Hotels with Pool & Resorts in South Side from AU$165

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Check prices for these dates

Tonight
8 Nov - 9 Nov
Tomorrow
9 Nov - 10 Nov
Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov

Our top choices for South Side hotels with a pool

A swimming pool with lounge chairs and tables, surrounded by large windows.

1. Chicago Marriott Midway

Chicago Marriott Midway
3.5 star property
Bedford Park
8.4 out of 10, Very good, (1,004 reviews)
  • cleanliness
    Splash into luxury at Chicago Marriott Midway's indoor pool, open from 5 AM to 11 PM for all-day aquatic enjoyment.
The price is AU$245
includes taxes & fees
22 Nov - 23 Nov
Chicago Marriott Midway
Pool

2. Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,530 reviews)
  • cleanliness
    Soak in relaxation at this historic Chicago hotel's indoor pool with spa amenities nearby.
The price is AU$230
includes taxes & fees
27 Nov - 28 Nov
Hilton Chicago
A modern indoor swimming pool with clear glass walls, a poolside seating area with chairs, and large windows offering views of the outside.

3. Hampton Inn Chicago McCormick Place

Hampton Inn Chicago McCormick Place
3.0 star property
South Loop
9.0 out of 10, Wonderful, (1,042 reviews)
  • cleanliness
    Dive into a refreshing Chicago escape at this hotel with an indoor pool, steps from Wintrust Arena and McCormick Place.
The price is AU$175
includes taxes & fees
23 Nov - 24 Nov
Hampton Inn Chicago McCormick Place
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

4. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,196 reviews)
  • cleanliness
    Dive into city centre luxury with a rejuvenating pool experience close to Chicago landmarks.
The price is AU$166
includes taxes & fees
9 Dec - 10 Dec
Hilton Garden Inn Chicago Downtown South Loop
An indoor swimming pool with a skylight, tiled floor, and poolside seating.

5. Hampton Inn & Suites Chicago Downtown

Hampton Inn & Suites Chicago Downtown
3.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,593 reviews)
  • cleanliness
    Splash into city centre luxury at this Hampton Inn with stylish indoor pool and river proximity.
The price is AU$173
includes taxes & fees
8 Dec - 9 Dec
Hampton Inn & Suites Chicago Downtown
An indoor swimming pool with lounge chairs and tables, a tiled floor, and a ceiling with a unique light fixture.

6. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (3,018 reviews)
  • cleanliness
    Chicago hotel offers refreshing stays with indoor pool, fitness centre, and walkable Michigan Avenue access.
The price is AU$248
includes taxes & fees
24 Nov - 25 Nov
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
An indoor swimming pool with lounge chairs and exercise equipment.

7. Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,117 reviews)
  • cleanliness
    Splash into serenity at this Michigan Avenue retreat with a sparkling indoor pool, spa pool haven, and 24-hour fitness centre.
The price is AU$233
includes taxes & fees
23 Nov - 24 Nov
Hyatt Centric Chicago Magnificent Mile
A swimming pool with lounge chairs and a wall with a patterned design.

8. Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,700 reviews)
  • cleanliness
    Dive into modern bliss at this city centre hotel, where the indoor pool sparkles alongside skyline views.
The price is AU$204
includes taxes & fees
23 Nov - 24 Nov
Hyatt Place Chicago/Downtown - The Loop
A modern indoor swimming pool with clear glass walls, a seating area with chairs and red vases, and large windows offering a view of the city.

9. Home2 Suites by Hilton Chicago McCormick Place

Home2 Suites by Hilton Chicago McCormick Place
3.0 star property
South Loop
9.2 out of 10, Wonderful, (956 reviews)
The price is AU$195
includes taxes & fees
3 Dec - 4 Dec
Home2 Suites by Hilton Chicago McCormick Place
A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

10. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,582 reviews)
  • cleanliness
    Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.
The price is AU$168
includes taxes & fees
7 Dec - 8 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
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.
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Choose what matters most at hotels with a pool in South Side

Breakfast included
4 stars

Top South Side Hotel Reviews

A swimming pool area with a glass-bottomed pool, a high ceiling with hanging lights, and a staircase with people sitting on it.
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago

10/10 Excellent

staff were very friendly and helpful
Australia
Simon
Reviewed September 3, 2026
InterContinental Chicago Magnificent Mile by IHG

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