Hotels with Swimming Pools in 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 Chicago Hotels with Swimming Pools

This weekend
29 May - 31 May
Next weekend
5 Jun - 7 Jun

Our top choices for Chicago hotels with a pool

Indoor pool

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (4,350 reviews)
The price is S$264
includes taxes & fees
28 Jun - 29 Jun
Hilton Chicago/Magnificent Mile Suites
Indoor pool, open 7:00 AM to 10:00 PM, pool loungers

Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,261 reviews)
  • cleanliness
    Splash into the city at this city centre hotel with a sleek indoor pool, stylish loungers, and a vibrant atmosphere to match.
The price is S$253
includes taxes & fees
29 Jun - 30 Jun
Aloft by Marriott Chicago Mag Mile
Outdoor pool, pool cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,492 reviews)
  • cleanliness
    Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.
The price is S$321
includes taxes & fees
29 Jun - 30 Jun
DoubleTree by Hilton Chicago - Magnificent Mile
Indoor pool, open 5:00 AM to 11:00 PM, pool loungers

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3,785 reviews)
  • cleanliness
    Dive into the Chicago city centre hotel's refreshing indoor pool and sauna for ultimate relaxation.
The price is S$332
includes taxes & fees
28 Jun - 29 Jun
voco Chicago Downtown - Riverwalk by IHG
Pool

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,016 reviews)
  • cleanliness
    Dive into city centre luxury with a rejuvenating pool experience close to Chicago landmarks.
The price is S$302
includes taxes & fees
29 Jun - 30 Jun
Hilton Garden Inn Chicago Downtown South Loop
Indoor pool, seasonal outdoor pool, free pool cabanas, pool loungers

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,948 reviews)
  • cleanliness
    Luxurious indoor and seasonal outdoor pools form a relaxing oasis near Millennium Park and Michigan Avenue.
The price is S$425
includes taxes & fees
14 Jun - 15 Jun
Radisson Blu Aqua Hotel Chicago
Indoor pool

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,615 reviews)
  • cleanliness
    Stylish indoor pool retreat in city centre Chicago makes luxury laps a breeze after sightseeing.
The price is S$343
includes taxes & fees
28 Jun - 29 Jun
The Royal Sonesta Chicago River North
Seasonal outdoor pool, open 8:00 AM to 10:00 PM, pool loungers

Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,009 reviews)
  • cleanliness
    A refreshing seasonal escape awaits at this Chicago hotel's sun-drenched pool area.
The price is S$281
includes taxes & fees
14 Jun - 15 Jun
Holiday Inn & Suites Chicago - Downtown by IHG
Seasonal outdoor pool, pool loungers

Viceroy Chicago

Viceroy Chicago
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,234 reviews)
  • cleanliness
    Splash into the city centre scene at this luxury Chicago hotel with a rooftop pool and complimentary bicycles.
The price is S$490
includes taxes & fees
28 Jun - 29 Jun
Viceroy Chicago
Indoor pool

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,101 reviews)
  • cleanliness
    Splash into serenity at this Michigan Avenue retreat with a sparkling indoor pool, hot tub haven, and 24-hour fitness centre.
The price is S$354
includes taxes & fees
30 Jun - 1 Jul
Hyatt Centric Chicago Magnificent Mile
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Choose what matters most at hotels with a pool in Chicago

Breakfast included
Hot tub

Hotels with pools and free breakfast in Chicago

Exterior
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (4350)
The price is S$264
includes taxes & fees
28 Jun - 29 Jun
Hilton Chicago/Magnificent Mile Suites
View all properties

Hotels with pools and hot tubs in Chicago

Exterior
Hilton Chicago

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2835)
The price is S$400
includes taxes & fees
30 Jun - 1 Jul
Hilton Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Chicago Hotel Reviews

Hilton Chicago

Hilton Chicago

10/10 Excellent
"We liked every thing at this hotel. Thank you!"
Haleh 4-night trip
Posted 1 hour ago
Hilton Chicago

Frequently asked questions

What's it like visiting Chicago?
If lounging by a pool is your idea of a great holiday, you might want to think about lively Chicago, which offers 139 places to stay with pools. While you're visiting, you can explore attractions such as Michigan Avenue and Soldier Field, and then kick back and relax poolside at one of the accommodation options in Chicago that guests like for their pools.
What are some hotels with pools in Chicago?
Embassy Suites by Hilton Chicago Downtown River North: Hotel, 4-minute walk from Michigan Avenue. Features full, an indoor pool and flat-screen televisions. Embassy Suites by Hilton Chicago O'Hare Rosemont: Hotel, 3-minute walk from Donald E. Stephens Convention Center. Offers buffet, an indoor pool and a 24-hour fitness centre. Hilton Garden Inn Chicago Downtown South Loop: Hotel, 1-minute walk from State Street. Provides a snack bar/deli, a pool and complimentary wireless Internet access. Holiday Inn & Suites Chicago - Downtown by IHG: Hotel, 10-minute walk from Willis Tower. Features a snack bar/deli, a seasonal outdoor pool and complimentary wireless Internet access. Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG: Hotel steps from Rosemont Theatre. Offers 3 restaurants, an indoor pool and complimentary wireless Internet access.
How many hotels with pools should I expect to find in Chicago?
Expedia's 139 hotels in Chicago give you a great choice for your poolside getaway.
What is there to see and do in Chicago?
Explore places such as Wrigley Field, Michigan Avenue and Soldier Field while you're in Chicago. Surround yourself with nature at Millennium Park and Grant Park. Visitors have positive things to say about the popular theatre scene and stunning architecture in Chicago.
When is the best time to book a hotel with a pool in Chicago?
You may want to think about accommodation with an outdoor swimming pool if you're planning to visit Chicago in the warmest months of July, August or June, when the average temperature is 21°C. Accommodation offering an indoor pool may be what you want if you are visiting during the coldest months of January, February or December, when the average temperature is -1°C.
What's the best way to travel around Chicago?
Knowing the transportation options in Chicago can help you enjoy the area beyond your hotel pool. You can access metro transport at Monroe Station (Red Line), Monroe Station (Blue Line) and Adams-Wabash Station. If you'd like to venture out around the area, you may want to rent a car for your trip.

Explore a world of travel with Expedia