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Hotels with Swimming Pool in South Side, Chicago

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Check availability on South Side Hotels with Swimming Pool

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

Our top choices for South Side hotels with a pool

A swimming pool with lounge chairs and tables, surrounded by large windows.
A bar area with a black marble countertop, wicker bar stools, and a variety of bottles and glasses on shelves.
A modern bar area with high stools, a bar counter, and a seating area with round tables and chairs.

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.
P11,047
P12,978 total
includes taxes & fees
Aug 31 - Sep 1
Chicago Marriott Midway
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.
A modern hotel entrance with glass doors, a visible reception desk, and signage for Hilton Garden Inn and Homewood Suites.
A modern hotel lobby with a reception desk, seating area, and a large window providing a view of the outdoors.
A hot tub with a metal ladder, surrounded by white tiled walls and floor, with a large window providing a view of the cityscape.

2. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
  • Dive into downtown luxury with a rejuvenating pool experience close to Chicago landmarks.
P9,392
P11,026 total
includes taxes & fees
Sep 7 - Sep 8
Hilton Garden Inn Chicago Downtown South Loop
A swimming pool with lounge chairs and sun loungers, a tiled floor, and a large window with curtains.
A hotel room with a sofa, armchair, a flat-screen TV, a bed, and a view of the city and ocean.
A hotel room with a bed, a desk, a television, a sofa, and a large window with a city view.
A cityscape at dusk with high-rise buildings, including a Hilton hotel.

3. Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
P9,914
P11,787 total
includes taxes & fees
Aug 30 - Aug 31
Hilton Chicago/Magnificent Mile Suites
An indoor swimming pool with lounge chairs and a no diving sign.
A modern hotel lobby with multiple dining areas, a central food station, and a high-ceiling atrium with balconies.
A hotel room with two beds, a large window with a city view, a wooden wardrobe, and a bedside table with a lamp.
A hotel reception area with a black reception desk, a concierge service sign, and a tiled floor.

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 center, and walkable Michigan Avenue access.
P8,865
P12,351 total
includes taxes & fees
Aug 31 - Sep 1
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.
A hotel reception area with a modern design, featuring a wooden panel wall and a marble reception desk.
A cozy room with a patterned carpet, a wooden table, and a green sofa with a white throw blanket.
A modern hotel lobby with a central seating area, a staircase, and a wall with a vertical garden.

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.
P9,390
P11,163 total
includes taxes & fees
Aug 30 - Aug 31
DoubleTree by Hilton Chicago - Magnificent Mile
A modern indoor swimming pool with blue seating and a view of the city through large windows.
A modern high-rise hotel with multiple floors, large windows, and a well-lit entrance area.
A modern hotel room with a bed, a sofa, a coffee table with flowers, a TV, and a large window with a city view.

6. Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
Downtown Chicago
  • Splash into the city at this downtown hotel with a sleek indoor pool, stylish loungers, and a vibrant atmosphere to match.
P9,504
P11,299 total
includes taxes & fees
Sep 7 - Sep 8
Aloft by Marriott Chicago Mag Mile
A rooftop pool with lounge chairs and potted plants, surrounded by modern buildings.
A modern reception area with two desks, a large window, and a city view.
A spacious lobby with two elevators, a reception area, and a seating area with blue and white ottomans.
A modern building with large glass windows and a covered walkway.

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.
P9,195
P11,673 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn & Suites Chicago - Downtown by IHG
A swimming pool with lounge chairs and a wall with a patterned design.
A gym with cardio machines, weight benches, and a large window offering a city view.
A hotel room with a large bed, a desk with a chair, a sofa, and a TV.
A modern hotel with a glass facade, multiple floors, and a visible entrance.

8. Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop
Downtown Chicago
  • Dive into modern bliss at this downtown hotel, where the indoor pool sparkles alongside skyline views.
P10,430
P12,400 total
includes taxes & fees
Sep 7 - Sep 8
Hyatt Place Chicago/Downtown - The Loop
A large indoor swimming pool with clear blue water, surrounded by windows offering views of a cityscape.
A hotel room with a large window offering a city view, a bed, a desk, and a chair.
A bar area with a granite countertop, bar stools, and a variety of bottles and glasses.
A coffee shop interior with a display case of pastries, a coffee machine, and a menu board.

9. Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
Downtown Chicago
P8,859
P10,532 total
includes taxes & fees
Sep 7 - Sep 8
Courtyard by Marriott Chicago Magnificent Mile
An indoor swimming pool with lounge chairs and exercise equipment.
A modern workspace with two Apple iMacs, a desk with a keyboard, and a bookshelf filled with books and decorative items.
A bar area with a modern design, featuring a long counter and multiple seating options.
A multi-story building with a Starbucks Coffee on the ground floor, emergency exit signs, and a Hyatt Center sign.

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 center.
P10,430
P14,234 total
includes taxes & fees
Aug 31 - Sep 1
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

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