Photo by by Midway Intl Airport

Hotels with Swimming Pool in South Side, Chicago

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check availability on South Side Hotels with Swimming Pool

This weekend
Next weekend

Top South Side Hotels with Swimming Pool

Chicago Marriott Midway
3.5 star property
  • Indoor pool
8.4 out of 10, Very Good, (903)
Swimming sessions stretch from early morning until late evening in the indoor pool, a cherished feature of this Art Deco hotel. After laps, guests appreciate the adjacent 24-hour fitness center, complimentary airport transportation, and on-site American cuisine at Copper Fox.
The price is P8,481
P9,963 total
includes taxes & fees
Nov 13 - Nov 14
Chicago Marriott Midway
voco Chicago Downtown - Riverwalk by IHG
3.5 star property
  • Indoor pool
  • Pool loungers
  • Near the beach
8.8 out of 10, Excellent, (3321)
Swimmers delight in the spacious indoor pool with glass roof, accessing refreshing waters from early morning until late evening. After laps, guests unwind on comfortable loungers or detoxify in the sauna before dining at the riverside restaurant.
The price is P5,236
P6,147 total
includes taxes & fees
Nov 24 - Nov 25
voco Chicago Downtown - Riverwalk by IHG
Palmer House a Hilton Hotel
4.0 star property
  • Indoor pool
  • Near the beach
  • Full-service spa
8.4 out of 10, Very Good, (2068)
Sophisticated swimmers relish the year-round indoor pool at this historic treasure near Millennium Park. After invigorating laps, guests can indulge in spa treatments, workout at the 24-hour health club, or explore nearby Chicago landmarks.
The price is P6,451
P9,044 total
includes taxes & fees
Nov 24 - Nov 25
Palmer House a Hilton Hotel
The Wade
4.5 star property
  • Indoor pool
  • Near the beach
8.4 out of 10, Very Good, (1415)
Sparkling waters beckon in the sleek indoor pool, a serene oasis amid Chicago's urban energy. Guests appreciate the 5:00 AM to 11:00 PM access, perfect for refreshing dips before exploring Navy Pier or after fitness classes at the 24-hour gym.
The price is P6,060
P7,114 total
includes taxes & fees
Dec 7 - Dec 8
The Wade
Hyatt Centric Chicago Magnificent Mile
4.0 star property
  • Indoor pool
  • Near the beach
  • Hot tub
9.0 out of 10, Wonderful, (1026)
Bubbling relaxation awaits in the pristine indoor pool and soothing hot tub, perfect complements to an invigorating workout in the state-of-the-art fitness center. Steps from Chicago's Riverwalk and Millennium Park, this hotel combines aquatic tranquility with urban adventure.
The price is P5,766
P8,495 total
includes taxes & fees
Dec 7 - Dec 8
Hyatt Centric Chicago Magnificent Mile
Aloft Chicago Mag Mile
3.0 star property
  • Indoor pool
  • Pool loungers
  • Near the beach
8.6 out of 10, Excellent, (2879)
Dive into relaxation at the inviting indoor pool, perfectly complementing days spent exploring nearby Millennium Park and Navy Pier. Sun loungers provide comfortable respite, while the fitness center with city views offers 24-hour workout options.
The price is P5,356
P6,287 total
includes taxes & fees
Nov 23 - Nov 24
Aloft Chicago Mag Mile
DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
  • Outdoor pool
  • Poolside bar
  • Pool loungers
  • Near the beach
8.8 out of 10, Excellent, (2128)
Poolside bliss awaits with shaded cabanas, comfortable loungers, and refreshing cocktails from the bar. After swimming, guests can explore Michigan Avenue's attractions, dine at HotHouse restaurant, or energize in the fitness center.
The price is P5,572
P6,541 total
includes taxes & fees
Nov 23 - Nov 24
DoubleTree by Hilton Chicago - Magnificent Mile
Radisson Blu Aqua Hotel Chicago
4.5 star property
  • Indoor pool
  • Pool loungers
  • Near the beach
8.6 out of 10, Excellent, (1744)
Splash into aquatic bliss at both indoor and seasonal outdoor pools complete with complimentary cabanas and sun loungers. This luxury hotel offers basketball courts, FireLake restaurant, and sits within walking distance of Chicago Riverwalk and Millennium Park.
The price is P8,189
P11,135 total
includes taxes & fees
Nov 23 - Nov 24
Radisson Blu Aqua Hotel Chicago
The Royal Sonesta Chicago River North
4.5 star property
  • Indoor pool
  • Near the beach
9.2 out of 10, Wonderful, (2224)
Sink into luxurious pool loungers at the inviting indoor sanctuary after exploring nearby Michigan Avenue. Featuring a 24-hour fitness center, on-site restaurant, and terrace, this hotel perfectly combines aquatic relaxation with urban adventure.
The price is P6,060
P8,997 total
includes taxes & fees
Dec 7 - Dec 8
The Royal Sonesta Chicago River North
Holiday Inn Chicago Dwtn - The Mart by IHG
3.0 star property
  • Indoor pool
  • Near the beach
8.8 out of 10, Excellent, (1978)
Dive into the warm indoor pool at this riverfront Chicago hotel, open from 5:00 AM to 11:00 PM daily. Recently renovated rooms showcase stunning skyline vistas, while kayaking adventures and riverside dining await just steps away.
The price is P5,677
P6,665 total
includes taxes & fees
Nov 24 - Nov 25
Holiday Inn Chicago Dwtn - The Mart by IHG
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.

Top South Side Hotel Reviews

Explore a world of travel with Expedia