A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.

Hotels with Swimming Pools 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 availability on South Side Hotels with Swimming Pools

Tonight
24 Aug - 25 Aug
Tomorrow
25 Aug - 26 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Our top choices for South Side hotels with a pool

1. Chicago Marriott Midway

Chicago Marriott Midway
Bedford Park
  • Splash into luxury at Chicago Marriott Midway's indoor pool, open from 5 AM to 11 PM for all-day aquatic enjoyment.
S$267
includes taxes & fees
31 Aug - 1 Sept
Chicago Marriott Midway

2. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
  • Dive into city centre luxury with a rejuvenating pool experience close to Chicago landmarks.
S$227
includes taxes & fees
7 Sept - 8 Sept
Hilton Garden Inn Chicago Downtown South Loop

3. Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
S$219
includes taxes & fees
1 Sept - 2 Sept
Hilton Chicago/Magnificent Mile Suites

4. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Downtown Chicago
  • Chicago hotel offers refreshing stays with indoor pool, fitness centre, and walkable Michigan Avenue access.
S$255
includes taxes & fees
1 Sept - 2 Sept
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

5. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
Downtown Chicago
  • Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.
S$230
includes taxes & fees
31 Aug - 1 Sept
DoubleTree by Hilton Chicago - Magnificent Mile

6. Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
Downtown Chicago
  • Splash into the city at this city centre hotel with a sleek indoor pool, stylish loungers, and a vibrant atmosphere to match.
S$232
includes taxes & fees
7 Sept - 8 Sept
Aloft by Marriott Chicago Mag Mile

7. Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG
Downtown Chicago
  • A refreshing seasonal escape awaits at this Chicago hotel's sun-drenched pool area.
S$240
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn & Suites Chicago - Downtown by IHG

8. Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop
Downtown Chicago
  • Dive into modern bliss at this city centre hotel, where the indoor pool sparkles alongside skyline views.
S$255
includes taxes & fees
7 Sept - 8 Sept
Hyatt Place Chicago/Downtown - The Loop

9. Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
Downtown Chicago
S$217
includes taxes & fees
7 Sept - 8 Sept
Courtyard by Marriott Chicago Magnificent Mile

10. Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
  • Splash into serenity at this Michigan Avenue retreat with a sparkling indoor pool, hot tub haven, and 24-hour fitness centre.
S$293
includes taxes & fees
31 Aug - 1 Sept
Hyatt Centric Chicago Magnificent Mile
View all properties

Choose what matters most at hotels with a pool in South Side

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top South Side Hotel Reviews

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

8/10 Good
"."
Brigid 5-night trip
Posted 3 hours ago
Holiday Inn Chicago – Midway Airport S by IHG
Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

10/10 Excellent
"We loved the hotel's warm, friendly atmosphere, the staff was great, our room was clean and quiet, the breakfast was good, and it was a good location to visit the Obama Presidential Center."
Rosalee J. 2-night trip
Posted 1 day ago
Hyatt Place Chicago-South/University Medical Center
Best Western Inn & Suites - Midway Airport

Best Western Inn & Suites - Midway Airport

10/10 Excellent
"It was one of the cleanest and most attractive hotel rooms I've ever stayed in. The price was reasonable at $199 (1 night), and it was close to Chicago Midway Airport (about 12 minutes with traffic). The staff was very friendly and helpful, and the included breakfast was the best and most elegant I've seen at any hotel that offers breakfast (even better than the à la carte breakfast). The building was undergoing maintenance with some renovations in progress, but it was still clean, well-lit, and had excellent rooms. The staff was well-dressed and conducted themselves properly. The only "bad" thing I have to say about this hotel is that the iron didn't work. Air conditioning works properly, had a big TV in room."
Jeannette 1-night trip
Posted 2 days ago
Best Western Inn & Suites - Midway Airport

Explore a world of travel with Expedia