Find Hotels with Pool in Chicago, IL

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Check availability on Chicago Hotels with Pool

Tonight
4 Aug - 5 Aug
Tomorrow
5 Aug - 6 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Top Chicago Hotels with Pool

The Wade
Enjoy a sea view from the large window, with a comfortable seating area and unique artwork on display.

The Wade

4.5 star property
8.2 out of 10, Very good, (1153)
"It was a very relaxing stay and amazing view!"
The price is £105
includes taxes & fees
1 Sept - 2 Sept
The Wade
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Relax by the pool surrounded by comfortable seating and city views.

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
8.4 out of 10, Very good, (3631)
"Great stay. "
The price is £127
includes taxes & fees
24 Aug - 25 Aug
Hilton Garden Inn Chicago Downtown/Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
Relax by the pool surrounded by lounge chairs and umbrellas, taking in the city skyline views.

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1955)
"Very pleasant stay!"
The price is £141
includes taxes & fees
1 Sept - 2 Sept
DoubleTree by Hilton Chicago - Magnificent Mile
Aloft Chicago Mag Mile
Relax by the pool surrounded by comfortable seating and lush greenery.

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2780)
"We love our stay here !"
The price is £108
includes taxes & fees
17 Aug - 18 Aug
Aloft Chicago Mag Mile
Palmer House a Hilton Hotel
Relax by the pool surrounded by comfortable lounge chairs and framed artwork.

Palmer House a Hilton Hotel

4.0 star property
8.4 out of 10, Very good, (1826)
"Nice place to stay"
The price is £172
includes taxes & fees
21 Aug - 22 Aug
Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown South Loop
Relax by the pool with expansive city views.

Hilton Garden Inn Chicago Downtown South Loop

3.0 star property
8.8 out of 10, Excellent, (1613)
"Perfect for a 2 night stay, reasonable rate at a great location."
The price is £121
includes taxes & fees
25 Aug - 26 Aug
Hilton Garden Inn Chicago Downtown South Loop
The Hoxton Chicago
Relax by the rooftop pool with a stunning city view, surrounded by comfortable lounge chairs and a small table.

The Hoxton Chicago

4.0 star property
9.0 out of 10, Wonderful, (1003)
"Excellent location and great vibe. "
The price is £185
includes taxes & fees
17 Aug - 18 Aug
The Hoxton Chicago
Best Western River North Hotel
Relax by the rectangular pool surrounded by lounge chairs and umbrellas.

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1029)
"Good budget hotel"
The price is £109
includes taxes & fees
24 Aug - 25 Aug
Best Western River North Hotel
Sheraton Grand Chicago Riverwalk
Enjoy a scenic view of the river from this balcony, which features a treadmill and stationary bike for a workout.

Sheraton Grand Chicago Riverwalk

4.0 star property
8.4 out of 10, Very good, (1413)
" Great stay, helpful staff, perfectly located. "
The price is £202
includes taxes & fees
24 Aug - 25 Aug
Sheraton Grand Chicago Riverwalk
Homewood Suites by Hilton Chicago Downtown South Loop
Relax by the pool with expansive city views.

Homewood Suites by Hilton Chicago Downtown South Loop

3.0 star property
8.8 out of 10, Excellent, (2000)
"Was a great location just a few blocks from the beach. "
The price is £123
includes taxes & fees
24 Aug - 25 Aug
Homewood Suites by Hilton Chicago Downtown South Loop
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

The Wade

The Wade

10/10 Excellent
"The staff is wonderful. Everyone is very attentive to customer needs. The room was just spacious enough. The beds were comfortable. I love a hotel that provides bottles of water in the room at no additional cost. I have only two minor complaints. First, there was only one bar of soap provided. We need two - one for the shower and one for the sink. There were no other soap or body wash options either. Second, (and this is a pet peeve of mine), when reservations are made in advance and you know how many are staying in the room, please be sure there are enough towels and wash cloths for each. Two of the three nights I had to call the front desk and ask for towels and soap. I appreciate the staff’s promptness. "
Tara 3-night trip
Posted 8 hours ago
The Wade

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 48 places to stay with pools. While you're visiting, you can explore attractions such as Michigan Avenue and Navy Pier, 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. Holiday Inn & Suites Chicago - Downtown by IHG: Hotel, 10-minute walk from Willis Tower. Offers a snack bar/deli, a seasonal outdoor pool and complimentary wireless Internet access. Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG: Hotel, 4-minute walk from Donald E. Stephens Convention Center. Provides 3 restaurants, an indoor pool and complimentary wireless Internet access. Hilton Garden Inn Chicago Downtown South Loop: Hotel, 1-minute walk from State Street. Features a snack bar/deli, a pool and complimentary wireless Internet access. Hyatt Centric Chicago Magnificent Mile: Hotel, 2-minute walk from Michigan Avenue. Offers complimentary wireless Internet access, an indoor pool and a 24-hour fitness centre.
How many hotels with pools should I expect to find in Chicago?
Expedia's 48 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, Navy Pier and Wrigley 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.