Hotels with Pool & Resorts in South Side from NZ$205

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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 NZ$303
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 NZ$284
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 NZ$217
includes taxes & fees
23 Nov - 24 Nov
Hampton Inn Chicago McCormick Place
An indoor swimming pool with a skylight, tiled floor, and poolside seating.

4. 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 NZ$215
includes taxes & fees
8 Dec - 9 Dec
Hampton Inn & Suites Chicago Downtown
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

5. 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 NZ$205
includes taxes & fees
9 Dec - 10 Dec
Hilton Garden Inn Chicago Downtown South Loop
A swimming pool with lounge chairs and a sunbed, large windows, and a view of buildings outside.

6. Hyatt Place Chicago Midway Airport

Hyatt Place Chicago Midway Airport
3.0 star property
Bedford Park
9.0 out of 10, Wonderful, (1,350 reviews)
  • cleanliness
    Sun-drenched afternoons await at this indoor pool retreat with refreshing amenities and comfort.
The price is NZ$284
includes taxes & fees
4 Dec - 5 Dec
Hyatt Place Chicago Midway Airport
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 NZ$306
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.

8. 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 NZ$289
includes taxes & fees
23 Nov - 24 Nov
Hyatt Centric Chicago Magnificent Mile
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 NZ$241
includes taxes & fees
3 Dec - 4 Dec
Home2 Suites by Hilton Chicago McCormick Place
A modern indoor swimming pool with clear blue water, large windows offering city views, and a poolside area with chairs and a sun lounger.

10. Hyatt House Chicago/West Loop-Fulton Market

Hyatt House Chicago/West Loop-Fulton Market
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,311 reviews)
  • cleanliness
    Splashy indoor pool luxury awaits with designer touches in Chicago's West Loop scene.
The price is NZ$320
includes taxes & fees
22 Nov - 23 Nov
Hyatt House Chicago/West Loop-Fulton Market
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

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

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