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

Hotels with Swimming Pool in South Side, Chicago

  • 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 Pool

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

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.
Lobby lounge
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.
P11,245
P13,211 total
includes taxes & fees
Oct 26 - Oct 27
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-level atrium with a central spiral staircase, multiple seating areas, and a pool.

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.
P9,272
P12,637 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 lobby with a sofa set, a coffee table, and a large abstract wall art piece.
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 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.
P9,560
P11,231 total
includes taxes & fees
Nov 1 - Nov 2
Hyatt Place Chicago Midway Airport
A swimming pool area with a glass-bottomed pool, a high ceiling with hanging lights, and a staircase with people sitting on it.
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.
A person sitting by a window with a cityscape view.

4. 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.
P13,318
P18,033 total
includes taxes & fees
Oct 31 - Nov 1
InterContinental Chicago Magnificent Mile by IHG
An indoor swimming pool with a skylight, tiled floor, and poolside seating.
A modern restaurant with a long counter, bar stools, and high ceilings with exposed beams.
A modern hotel with a corner location, large windows, and a green awning.
A modern lobby with a reception desk, seating area, staircase, and decorative lighting.

5. 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.
P8,818
P10,508 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 grand hotel lobby with a high ceiling, a large chandelier, and a staircase leading to an upper floor.
A historic building with large windows and a marquee sign for a hotel.

6. JW Marriott Chicago

JW Marriott Chicago
Downtown Chicago
  • Sleek indoor pool sanctuary opens onto Chicago adventures in this luxury retreat.
P15,957
P21,212 total
includes taxes & fees
Oct 30 - Oct 31
JW Marriott Chicago
A modern hotel with a rooftop pool, surrounded by high-rise buildings and a clear view of the city skyline.
A modern interior with a staircase, glass railings, and a visible restaurant area.
A modern skyscraper with a unique wavy facade, surrounded by other high-rise buildings.
A nighttime cityscape with high-rise buildings, a curved architectural feature, and a well-lit urban area.

7. 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.
P14,871
P19,622 total
includes taxes & fees
Oct 31 - Nov 1
Radisson Blu Aqua Hotel Chicago
An indoor swimming pool with a skylight, lounge chairs, and potted plants.
A bar area with a long counter, metal bar stools, hanging pendant lights, and a variety of bottles on shelves.
An outdoor seating area with tables and chairs, surrounded by city buildings and a view of the urban skyline.
A bar area with a foosball table, seating, and a rustic brick wall.

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.
P17,484
P23,030 total
includes taxes & fees
Oct 31 - Nov 1
Renaissance Chicago Downtown Hotel
A modern indoor pool area with clear glass walls, lounge chairs, and a view of city buildings.
A modern interior with wooden flooring, black furniture, and large windows offering city views.
A rooftop lounge with green cushioned seating, a small round table, and a view of city buildings.
A modern restaurant interior with a green wall, hanging lights, and a long dining area.

9. Hotel 505 River North

Hotel 505 River North
Downtown Chicago
  • Stylish indoor pool retreat in downtown Chicago makes luxury laps a breeze after sightseeing.
P11,873
P16,127 total
includes taxes & fees
Nov 8 - Nov 9
Hotel 505 River North
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 modern hotel lobby with a reception desk, seating area, and artwork on the walls.
A hotel reception area with a counter displaying pastries and coffee, a coffee machine, and a golden clock.

10. 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.
P11,066
P13,156 total
includes taxes & fees
Oct 25 - Oct 26
Hampton Inn & Suites Chicago Medical District UIC
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

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

Explore a world of travel with Expedia