Search Hotels with Pool in Chicago

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Check availability on Chicago Hotels with Pool

Tonight
26 Dec - 27 Dec
Tomorrow
27 Dec - 28 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Chicago hotels with a pool

Indoor pool, open 7:00 AM to 10:00 PM, pool loungers
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2971)
"Great place to stay"
United States
Elisha
The price is Rp1.439.726
Rp1.690.094 total
includes taxes & fees
22 Jan - 23 Jan 2026
Aloft Chicago Mag 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

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3512)
"Really nice hotel"
United States
Saulius
The price is Rp1.693.352
Rp1.987.824 total
includes taxes & fees
28 Dec - 29 Dec
voco Chicago Downtown - Riverwalk by IHG
Outdoor pool, pool cabanas (surcharge), pool umbrellas
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2205)
"Great location, easy parking. "
United States
Maria
The price is Rp1.427.672
Rp1.675.946 total
includes taxes & fees
5 Jan - 6 Jan 2026
DoubleTree by Hilton Chicago - Magnificent Mile
Indoor pool
The Wade

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1536)
"Great staff and great location. "
United States
Joe
The price is Rp1.556.913
Rp1.827.660 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Wade
Indoor pool
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1052)
"Clean room, clean hotel, wonderful restaurant/bar. AMAZING location! "
United States
Rebecca
The price is Rp1.640.618
Rp2.417.271 total
includes taxes & fees
1 Jan - 2 Jan 2026
Hyatt Centric Chicago Magnificent Mile
Fitness facility
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (1579)
"Rooms were very nice and staff was great"
United States
Nancy
The price is Rp2.159.589
Rp3.037.373 total
includes taxes & fees
20 Jan - 21 Jan 2026
Sheraton Grand Chicago Riverwalk
Indoor pool
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (2757)
"Excellent place to stay "
United States
Teniesha
The price is Rp1.414.280
Rp2.151.573 total
includes taxes & fees
6 Jan - 7 Jan 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Indoor pool
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2062)
"Really nice rooms at a good rate "
United States
Madelyn
The price is Rp1.693.352
Rp1.987.824 total
includes taxes & fees
28 Dec - 29 Dec
Holiday Inn Chicago Dwtn - The Mart by IHG
Indoor pool
Hilton Chicago

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2415)
"What a great stay!!"
United States
Alejandra
The price is Rp2.045.415
Rp2.892.458 total
includes taxes & fees
1 Jan - 2 Jan 2026
Hilton Chicago
Indoor pool, seasonal outdoor pool, free pool cabanas, pool loungers
Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1791)
"Great hotel, close to shopping and restaurants, excellent customer service, highly recommend."
United States
Gina
The price is Rp2.235.928
Rp3.060.087 total
includes taxes & fees
28 Dec - 29 Dec
Radisson Blu Aqua Hotel 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.
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Top Chicago Hotel Reviews

Pendry Chicago

Pendry Chicago

10/10 Excellent
"The room was fantastic, the rest of the hotel (lobby, gym, bar) is spotless. We arranged an engagement photoshoot in the bar via Laura S (events coordinator) and she was unbelievably helpful in ensuring everything was done correctly and in line with hotel procedure. Will be staying again when we revisit Chicago! "
Connor 3-night trip
Posted 12 hours ago
Pendry 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 114 places to stay with pools. While you're visiting, you can explore attractions such as Michigan Avenue and Wrigley 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?
Homewood Suites by Hilton Chicago Downtown South Loop: Hotel, 2-minute walk from State Street. Features a snack bar/deli, a pool and buffet. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 4-minute walk from Michigan Avenue. Offers full, an indoor pool and flat-screen televisions. 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. Hyatt Centric Chicago Magnificent Mile: Hotel, 2-minute walk from Michigan Avenue. Features complimentary wireless Internet access, an indoor pool and a 24-hour fitness centre. Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG: Hotel, 4-minute walk from Donald E. Stephens Convention Center. 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 114 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 Michigan Avenue, Wrigley Field and Naval Base Great Lakes 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.