South Side Hotel Guide - Hotels with Pool in South Side, Chicago

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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 €151
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 €142
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 €108
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 €102
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 €107
includes taxes & fees
8 Dec - 9 Dec
Hampton Inn & Suites Chicago Downtown
An indoor swimming pool with lounge chairs and exercise equipment.

6. 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, hot tub haven, and 24-hour fitness centre.
The price is €144
includes taxes & fees
23 Nov - 24 Nov
Hyatt Centric Chicago Magnificent Mile
An indoor swimming pool with lounge chairs and tables, a tiled floor, and a ceiling with a unique light fixture.

7. 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 €152
includes taxes & fees
24 Nov - 25 Nov
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
A spacious indoor pool area with a clear view of the city through large windows, surrounded by wicker furniture and a clean, modern design.

8. Best Western River North Hotel

Best Western River North Hotel
2.5 star property
Downtown Chicago
7.8 out of 10, Good, (1,191 reviews)
  • cleanliness
    Splash into year-round pool fun at this Michigan Avenue hotel with a modern fitness centre.
The price is €85
includes taxes & fees
7 Dec - 8 Dec
Best Western River North Hotel
A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

9. 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 €103
includes taxes & fees
7 Dec - 8 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
An indoor swimming pool with lounge chairs and a sofa, large windows with a view of the city, and a high ceiling with skylights.

10. The Wade

The Wade
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,193 reviews)
  • cleanliness
    Float away at this stunning luxury hotel with an indoor pool overlooking Lake Michigan and the city's iconic skyline.
The price is €127
includes taxes & fees
23 Nov - 24 Nov
The Wade
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 person in a yellow swimsuit sitting on the edge of an indoor swimming pool with ornate white columns and patterned tiles.
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago

10/10 Excellent

Second time staying here and never fails to impress
Ireland
John
Reviewed August 16, 2025
InterContinental Chicago Magnificent Mile by IHG

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