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

  • 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 a Pool

Tonight
Oct 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

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 bar area with a black marble countertop, wicker bar stools, and a variety of bottles and glasses on shelves.
Lobby lounge

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$5,548
NT$6,518 total
includes taxes & fees
Nov 15 - Nov 16
Chicago Marriott Midway
A swimming pool with a glass wall, a seating area with sofas, and an exit sign.
A multi-level indoor area with a central water feature, surrounded by seating areas and greenery.
A spacious lobby with a central staircase, multiple floors, a reception desk, and seating areas.
A multi-story hotel with a prominent 'Embassy Suites' sign, a Starbucks Coffee shop, and a well-lit street at night.

2. Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
  • Slip into a vacation state of mind at Chicago's urban retreat with a sparkling indoor pool.
NT$4,311
NT$5,876 total
includes taxes & fees
Nov 1 - Nov 2
Embassy Suites by Hilton Chicago Downtown River North
A swimming pool with lounge chairs and a sunbed, large windows, and a view of buildings outside.
A modern reception area with a wooden reception desk, a seating area with sofas and a coffee table, and a large wall-mounted artwork.
A modern hotel with a glass facade, a covered entrance, and an American flag.
A modern bar area with wooden furniture, a beverage display, and a Starbucks logo.

3. 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.
NT$4,681
NT$5,499 total
includes taxes & fees
Nov 2 - Nov 3
Hyatt Place Chicago Midway Airport
An indoor swimming pool with a skylight, tiled floor, and poolside seating.
A modern hotel with a corner location, large windows, and a green awning.
A modern interior with a geometric light wall, a staircase, and hanging crystal chandeliers.
A modern lobby with a reception desk, seating area, staircase, and decorative lighting.

4. Hampton Inn & Suites Chicago Downtown

Hampton Inn & Suites Chicago Downtown
Downtown Chicago
  • Splash into downtown luxury at this Hampton Inn with stylish indoor pool and river proximity.
NT$5,050
NT$6,017 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn & Suites Chicago Downtown
A modern indoor swimming pool with clear blue water, lounge chairs, and a tiled wall with a blue mosaic pattern.
A modern reception area with a marble reception desk, a sofa, armchairs, and a coffee table.
A historic building with large windows and a marquee sign for a hotel.
A luxurious hotel lobby with marble columns, a polished floor, and ornate chandeliers.

5. JW Marriott Chicago

JW Marriott Chicago
Downtown Chicago
  • Sleek indoor pool sanctuary opens onto Chicago adventures in this luxury retreat.
NT$8,257
NT$10,976 total
includes taxes & fees
Oct 30 - Oct 31
JW Marriott Chicago
A swimming pool area with a glass-bottomed pool, a high ceiling with hanging lights, and a staircase with people sitting on it.
A person sitting by a window with a cityscape view.
The Intercontinental hotel facade with a large American flag and a floral display.
A bar area with a high bar counter, multiple stools, and a seating area with booths and tables.

6. InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
  • World-class indoor pool in downtown offers lap swimming and family fun at this luxury hotel.
NT$6,892
NT$9,331 total
includes taxes & fees
Oct 31 - Nov 1
InterContinental Chicago Magnificent Mile by IHG
A modern indoor pool area with lounge chairs, a wooden table, and large windows.
A modern hotel room with a large bed, a desk, a chair, a TV, and a sliding door leading to a shower area.
A hotel reception area with a counter displaying pastries and coffee, a coffee machine, and a golden clock.
A modern hotel lobby with a reception desk, seating area, and artwork on the walls.

7. Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC
Near West Side
  • Sleek indoor pool oasis at Chicago medical district hotel offers year-round swimming bliss.
NT$6,186
NT$7,355 total
includes taxes & fees
Oct 25 - Oct 26
Hampton Inn & Suites Chicago Medical District UIC
An indoor swimming pool with a skylight, lounge chairs, and potted plants.
A spacious lobby with a high ceiling, large windows, and a central seating area with sofas and a coffee table.
An outdoor seating area with tables and chairs, surrounded by city buildings and a view of the urban skyline.
A bar area with a long counter, metal bar stools, hanging pendant lights, and a variety of bottles on shelves.

8. Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel
Downtown Chicago
  • Splash into pure relaxation at this downtown hotel's indoor pool with loungers and fitness center access.
NT$9,915
NT$12,947 total
includes taxes & fees
Nov 1 - Nov 2
Renaissance Chicago Downtown Hotel
A modern hotel with a rooftop pool, surrounded by high-rise buildings and a clear view of the city skyline.
An outdoor seating area with modern furniture and potted plants.
A nighttime cityscape with high-rise buildings, a curved architectural feature, and a well-lit urban area.
A modern skyscraper with a unique wavy facade, surrounded by other high-rise buildings.

9. Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
Downtown Chicago
  • Luxurious indoor and seasonal outdoor pools form a relaxing oasis near Millennium Park and Michigan Avenue.
NT$7,726
NT$10,194 total
includes taxes & fees
Nov 15 - Nov 16
Radisson Blu Aqua Hotel Chicago
An indoor swimming pool with clear water, surrounded by lounge chairs and a glass wall.
A modern lobby with a stone wall, a flat-screen TV, and a fireplace.
A spacious lobby with a modern reception desk, comfortable seating area, and large windows offering city views.
A modern kitchen with a marble countertop, a dish rack, and a buffet setup with various food items.

10. Homewood Suites by Hilton Chicago-Downtown

Homewood Suites by Hilton Chicago-Downtown
Downtown Chicago
NT$6,353
NT$7,553 total
includes taxes & fees
Oct 25 - Oct 26
Homewood Suites by Hilton Chicago-Downtown
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
"I had several towels the had stains on them. Staff wasn’t always pleasant."
Lucretia 5-night trip
Posted 4 hours ago
Holiday Inn Chicago – Midway Airport S by IHG
Chicago Marriott Midway

Chicago Marriott Midway

10/10 Excellent
"Except there’s a person in the room we’re checked in (guy stated that he was let it By someone so he can take a shower). We were given another room, everything was perfect"
Catherine Zaballero 4-night trip
Posted 23 hours ago
Chicago Marriott Midway

Explore a world of travel with Expedia