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

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Check availability on South Side Hotels with Swimming Pools

Tonight
9 Oct - 10 Oct
Tomorrow
10 Oct - 11 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for South Side hotels with a pool

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

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$269
includes taxes & fees
8 Nov - 9 Nov
Chicago Marriott Midway
Pool
A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.
A hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.
A restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.

2. Hilton Chicago

Hilton Chicago
Downtown Chicago
  • Soak in relaxation at this historic Chicago hotel's indoor pool with spa amenities nearby.
S$290
includes taxes & fees
30 Oct - 31 Oct
Hilton Chicago
An indoor swimming pool with clear blue water, surrounded by walls with large windows offering views of trees and buildings.
A modern hotel room with a gray sofa, a small wooden side table, a desk with a chair, a large flat-screen TV, and a window with a blue valance.
A conference room with a long table, chairs, and artwork on the walls.
A hotel room with a large bed, two bedside lamps, a wall-mounted clock, and a window with a view.

3. Hampton Inn & Suites Bridgeview Chicago

Hampton Inn & Suites Bridgeview Chicago
Summit
  • Soak in tranquility at this modern Chicago hotel with an inviting indoor pool, loungers, and 24-hour fitness centre nearby.
S$173
includes taxes & fees
26 Oct - 27 Oct
Hampton Inn & Suites Bridgeview Chicago
An indoor swimming pool with clear lane markers, a tiled floor, and ceiling beams.
A spacious lobby with a central seating area, a reception desk, and a modern chandelier.
An outdoor dining area with brick walls, string lights, and tables set for guests.
A hotel lobby with seating areas, a patterned carpet, and a large mirror.

4. DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip
Alsip
  • Swimming laps of luxury in Chicago's only indoor hotel pool with cushy loungers.
S$175
includes taxes & fees
1 Nov - 2 Nov
DoubleTree by Hilton Chicago - Alsip
A swimming pool with a lifeguard station, chairs, and a clock on the wall.
Reception
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.
S$163
includes taxes & fees
8 Nov - 9 Nov
Fairfield Inn and Suites by Marriott Chicago Midway Airport
An indoor swimming pool with a skylight, tiled floor, and poolside seating.
A modern lobby with a reception desk, seating area, staircase, and decorative lighting.
A modern restaurant with a long counter, bar stools, and high ceilings with exposed beams.
A modern interior with a geometric light wall, a staircase, and hanging crystal chandeliers.

6. Hampton Inn & Suites Chicago Downtown

Hampton Inn & Suites Chicago Downtown
Downtown Chicago
  • Splash into city centre luxury at this Hampton Inn with stylish indoor pool and river proximity.
S$216
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn & Suites Chicago Downtown
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 person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.
A modern bar area with high stools, a bar counter, and shelves of liquor bottles.

7. 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.
S$216
includes taxes & fees
1 Nov - 2 Nov
The Wade
An indoor swimming pool with lounge chairs and exercise equipment.
A multi-story building with a Starbucks Coffee on the ground floor, emergency exit signs, and a Hyatt Center sign.
A bar area with wooden paneling, a TV mounted above the bar, and a bartender preparing drinks.
A modern workspace with two Apple iMacs, a desk with a keyboard, and a bookshelf filled with books and decorative items.

8. 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$295
includes taxes & fees
31 Oct - 1 Nov
Hyatt Centric Chicago Magnificent Mile
A swimming pool with lounge chairs and a sunbed, large windows, and a view of buildings outside.
A modern lobby with a sofa set, a coffee table, and a large abstract wall art piece.
A modern bar area with wooden furniture, a beverage display, and a Starbucks logo.
A modern reception area with a wooden reception desk, a seating area with sofas and a coffee table, and a large wall-mounted artwork.

9. Hyatt Place Chicago Midway Airport

Hyatt Place Chicago Midway Airport
Bedford Park
  • Sun-drenched afternoons await at this indoor pool retreat with refreshing amenities and comfort.
S$229
includes taxes & fees
1 Nov - 2 Nov
Hyatt Place Chicago Midway Airport
An indoor swimming pool with lounge chairs and tables, a tiled floor, and a ceiling with a unique light fixture.
A modern hotel lobby with a seating area, a reception desk, and artwork on the walls.
A high-rise hotel with a prominent curved glass facade, multiple floors, and a visible "EMBASSY" sign.
A hotel room with a bed, a TV, a window with curtains, and a view of tall buildings.

10. 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$272
includes taxes & fees
1 Nov - 2 Nov
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
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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
"The location is wonderful, and if you're looking for a no-frills place to stay and you plan to be out and about all day, this is a great option. The building has seen better days, but it's everything we needed it to be. Also, it was very quiet for sleeping at night, very little traffic noise, etc. Would definitely stay here again."
Jennifer 2-night trip
Posted 3 days ago
Chinatown Hotel Chicago
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

10/10 Excellent
"Definitely a motel vibe, no elevator. Nice staff and clean rooms."
William 1-night trip
Posted 4 days ago
Chicago Lake Shore Hotel

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