Hotels with Swimming Pool in Chicago, Illinois

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Our top choices for Chicago hotels with a pool

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2996)
"Great place to stay"
United States
Elisha
The price is P5,052
P5,931 total
includes taxes & fees
Jan 22 - Jan 23, 2026
Aloft Chicago Mag 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, (2211)
"It was a beautiful stay "
United States
Donald
The price is P5,010
P5,881 total
includes taxes & fees
Jan 4 - Jan 5, 2026
DoubleTree by Hilton Chicago - Magnificent Mile

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very Good, (1545)
"Great staff and great location. "
United States
Joe
The price is P5,463
P6,414 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Wade

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3535)
"Really nice hotel"
United States
Saulius
The price is P6,815
P8,000 total
includes taxes & fees
Jan 26 - Jan 27, 2026
voco Chicago Downtown - Riverwalk by IHG

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1060)
"Clean room, clean hotel, wonderful restaurant/bar. AMAZING location! "
United States
Rebecca
The price is P5,757
P8,483 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hyatt Centric Chicago 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, (2769)
"Excellent place to stay "
United States
Teniesha
The price is P4,343
P6,822 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1800)
"Great hotel, close to shopping and restaurants, excellent customer service, highly recommend."
United States
Gina
The price is P7,846
P10,738 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Radisson Blu Aqua Hotel Chicago

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (2443)
"What a great stay!!"
United States
Alejandra
The price is P7,178
P10,150 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hilton Chicago

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (4288)
"Amazing staff and perfect location "
United States
Brandi
The price is P4,576
P5,372 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1632)
"It was an amazing hotel in the best location!"
United States
Natalia A
The price is P5,743
P6,741 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Courtyard by Marriott 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.

Top Chicago Hotel Reviews

Frequently asked questions

What's it like visiting Chicago?
If lounging by a pool is your idea of a great vacation, you may want to consider lively Chicago, which offers 114 places to stay with pools. While you're here, you can explore attractions like Michigan Avenue and Wrigley Field, and then kick back and relax poolside at one of the accommodations 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. Homewood Suites by Hilton Chicago Downtown South Loop: Hotel, 2-minute walk from State Street. Offers a snack bar/deli, a pool, and buffet. 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 center. 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 will I be able 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 like Michigan Avenue, Wrigley Field, and Naval Base Great Lakes while you're in Chicago. Surround yourself with nature at Millennium Park and Lake Michigan. Visitors have positive things to say about the popular theater 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 a place to stay that offers an outdoor pool if you're planning to visit Chicago in the warmest months of July, August, or June when the average temperature is 70°F. Lodging offering an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temperature is 31°F.
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. Take advantage of metro transit 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.