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

Find Hotels with a Pool in South Side, IL

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Check availability on South Side Hotels with a Pool

Tonight
Sep 21 - Sep 22
Tomorrow
Sep 22 - Sep 23
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for South Side hotels with a pool

A swimming pool with lounge chairs and tables, surrounded by large windows.
A modern bar area with high stools, a bar counter, and a seating area with round tables and chairs.
A hotel room with two beds, a desk, and a chair.

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.
NT$7,246
NT$8,513 total
includes taxes & fees
Sep 26 - Sep 27
Chicago Marriott Midway
An indoor swimming pool with lounge chairs and a sofa, large windows with a view of the city, and a high ceiling with skylights.
A modern hotel room with a large window offering a view of the sea and a cityscape. There is a seating area with a sofa and a small table.
A modern hotel lobby with a marble floor, seating areas, and a ceiling with a sky-like projection.
A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.

2. The Wade

The Wade
Downtown Chicago
  • Float away at this stunning luxury hotel with an indoor pool overlooking Lake Michigan and the city's iconic skyline.
NT$4,742
NT$5,638 total
includes taxes & fees
Sep 27 - Sep 28
The Wade
An indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.
A hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.
A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.
A large, historic building with a central courtyard surrounded by trees.

3. Hilton Chicago

Hilton Chicago
Downtown Chicago
  • Soak in relaxation at this historic Chicago hotel's indoor pool with spa amenities nearby.
NT$6,736
NT$8,942 total
includes taxes & fees
Oct 12 - Oct 13
Hilton Chicago
A hotel pool area with a clear view of the cityscape through large windows, a pool with a metal ladder, and several lounge chairs.
A hotel room with a grey sofa, a white armchair, a small round table, and two floor lamps.
A modern hotel with a glass facade, multiple floors, and a prominent sign.
A modern dining area with a central island, chairs, pendant lights, and a decorative wall with a motivational quote.

4. Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
Downtown Chicago
  • Splash into urban relaxation at this West Loop hotel's stylish indoor pool, where sun loungers invite post-sightseeing unwinding.
NT$6,551
NT$7,789 total
includes taxes & fees
Sep 27 - Sep 28
Hampton Inn Chicago West Loop Fulton Market Area
A swimming pool with a lifeguard station, chairs, and a clock on the wall.
A hotel lobby with a large dining table, several chairs, a small coffee table, and a fireplace.
A hotel room with two beds, a desk, a chair, and a lamp.

5. Fairfield Inn and Suites by Marriott Chicago Midway Airport

Fairfield Inn and Suites by Marriott Chicago Midway Airport
Bedford Park
  • Serene indoor pool sanctuary creates a refreshing escape after airport travel, with an all-season swimming haven for unwinding.
NT$3,841
NT$4,512 total
includes taxes & fees
Sep 28 - Sep 29
Fairfield Inn and Suites by Marriott Chicago Midway Airport
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 wooden paneling, a TV mounted above the bar, and a bartender preparing drinks.
A bar area with a modern design, featuring a long counter and multiple seating options.

6. 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.
NT$7,288
NT$9,610 total
includes taxes & fees
Oct 1 - Oct 2
Hyatt Centric Chicago Magnificent Mile
A modern indoor swimming pool with blue seating and a view of the city through large windows.
A modern hotel room with a bed, a sofa, a coffee table with flowers, a TV, and a large window with a city view.
A gym with treadmills, ellipticals, and weight machines.
A modern lobby with a grey sofa, checkered ottomans, and a coffee table. There are black chairs, a blue sofa, and a TV on a stand.

7. 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.
NT$6,587
NT$7,832 total
includes taxes & fees
Sep 27 - Sep 28
Aloft by Marriott Chicago Mag Mile
A large indoor swimming pool with clear blue water, surrounded by windows offering views of a cityscape.
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.
A hotel room with a large window offering a city view, a bed, a desk, and a chair.

8. Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
Downtown Chicago
NT$6,206
NT$7,378 total
includes taxes & fees
Sep 27 - Sep 28
Courtyard by Marriott Chicago Magnificent Mile
A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.
A modern hotel lobby with a central seating area, a staircase, and a wall with a vertical garden.
A cozy room with a patterned carpet, a wooden table, and a green sofa with a white throw blanket.
Transparent igloo-like structures with seating inside, set on a wooden deck with snow on the ground, surrounded by tall buildings.

9. 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.
NT$7,454
NT$8,862 total
includes taxes & fees
Sep 27 - Sep 28
DoubleTree by Hilton Chicago - Magnificent Mile
A spacious indoor pool area with a clear view of the city through large windows, surrounded by wicker furniture and a clean, modern design.
A rooftop terrace with lounge chairs and tables, offering a city skyline view.
A hotel room with a large bed, two armchairs, a wooden dresser, a desk with a chair, a flat-screen TV, and framed pictures on the wall.
A hotel lobby with a reception desk, seating area, and a view of the city.

10. Best Western River North Hotel

Best Western River North Hotel
Downtown Chicago
  • Splash into year-round pool fun at this Michigan Avenue hotel with a modern fitness center.
NT$5,383
NT$6,400 total
includes taxes & fees
Sep 27 - Sep 28
Best Western River North Hotel
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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

Chinatown Hotel Chicago

Chinatown Hotel Chicago

8/10 Good
"Was a nice place could use some TLC but overall nice and close to the L trains"
mark 4-night trip
Posted 3 hours ago
Chinatown Hotel Chicago
Best Western Inn & Suites - Midway Airport

Best Western Inn & Suites - Midway Airport

8/10 Good
"Room was clean, and we would definitely stay here again! Private and quiet. Also the Staff was very sweet. Parking is free as well. Breakfast is decent."
Celeste 4-night trip
Posted 4 hours ago
Best Western Inn & Suites - Midway Airport
Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

10/10 Excellent
"We had a late arrival"
Kelly 1-night trip
Posted 6 hours ago
Hyatt Place Chicago-South/University Medical Center
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

8/10 Good
"The lighting in the room was lacking in the bathroom and main area. There was only one light in the bathroom and the main area only had lights on one side of the room. Also the front desk staff was not available on check we had to ask other staff to locate them for assistance."
Wendel 1-night trip
Posted 1 day ago
Holiday Inn Chicago – Midway Airport S by IHG
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

8/10 Good
"The stairs were steep and are difficult for seniors. The air conditioning was really cool."
Dianne 1-night trip
Posted 2 days ago
Chicago Lake Shore Hotel

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