Search Hotels with Swimming Pool in South Side

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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 ₹13,429
₹15,777 total
includes taxes & fees
22 Nov - 23 Nov
Chicago Marriott Midway
A swimming pool with a glass wall, a seating area with sofas, and an exit sign.

2. Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (5,985 reviews)
  • cleanliness
    Slip into a holiday state of mind at Chicago's urban retreat with a sparkling indoor pool.
The price is ₹11,575
₹13,761 total
includes taxes & fees
7 Dec - 8 Dec
Embassy Suites by Hilton Chicago Downtown River North
A swimming pool with lounge chairs and a sunbed, large windows, and a view of buildings outside.

3. 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 ₹12,594
₹14,795 total
includes taxes & fees
4 Dec - 5 Dec
Hyatt Place Chicago Midway Airport
A modern indoor pool area with clear glass walls, lounge chairs, and a view of city buildings.

4. Hotel 505 River North

Hotel 505 River North
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (3,009 reviews)
  • cleanliness
    Stylish indoor pool retreat in city centre Chicago makes luxury laps a breeze after sightseeing.
The price is ₹12,010
₹17,284 total
includes taxes & fees
9 Dec - 10 Dec
Hotel 505 River North
A swimming pool area with a glass-bottomed pool, a high ceiling with hanging lights, and a staircase with people sitting on it.

5. InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (3,427 reviews)
  • cleanliness
    World-class indoor pool in city centre offers lap swimming and family fun at this luxury hotel.
The price is ₹17,562
₹24,166 total
includes taxes & fees
6 Dec - 7 Dec
InterContinental Chicago Magnificent Mile by IHG
An indoor swimming pool with clear windows, green chairs, and a tiled deck.

6. Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport
2.5 star property
Schiller Park
9.4 out of 10, Exceptional, (2,414 reviews)
  • cleanliness
    Splash into cool escape at Chicago O'Hare's serene indoor pool, perfect for year-round laps and leisure dips.
The price is ₹9,767
₹11,230 total
includes taxes & fees
29 Nov - 30 Nov
Hampton Inn Chicago-O'Hare International Airport
A modern indoor swimming pool with clear blue water, lounge chairs, and a tiled wall with a blue mosaic pattern.

7. JW Marriott Chicago

JW Marriott Chicago
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Sleek indoor pool sanctuary opens onto Chicago adventures in this luxury retreat.
The price is ₹17,468
₹24,117 total
includes taxes & fees
26 Nov - 27 Nov
JW Marriott Chicago
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.

8. 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, (957 reviews)
The price is ₹10,704
₹12,566 total
includes taxes & fees
3 Dec - 4 Dec
Home2 Suites by Hilton Chicago McCormick Place
A large indoor swimming pool with clear blue water, surrounded by windows offering views of a cityscape.

9. Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2,086 reviews)
The price is ₹10,344
₹12,299 total
includes taxes & fees
6 Dec - 7 Dec
Courtyard by Marriott Chicago Magnificent Mile
Pool

10. 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 ₹10,138
₹14,809 total
includes taxes & fees
27 Nov - 28 Nov
Hilton Chicago
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.
View all properties

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

Fantastic location. Excellent staff and service was sent
United Kingdom
David
Reviewed July 25, 2026
InterContinental Chicago Magnificent Mile by IHG

Explore a world of travel with Expedia