Chicago Hotels with a Pool

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Booking Insights
Recommended by KAYAK

Best Chicago hotels with a pool

These are the best prices for Mar 16 - 23.
DoubleTree by Hilton Hotel Chicago - Magnificent Mile - Chicago - Lounge
DoubleTree by Hilton Hotel Chicago - Magnificent Mile
Near North Side
8.0Very good(3008)
Free Wi-Fi
Pool
Pet friendly
C$ 276+
Check availability
Hilton Chicago - Chicago - Living room
Hilton Chicago
Downtown
7.9Good(2692)
Free Wi-Fi
Pool
Pet friendly
C$ 356+
Check availability
Embassy Suites by Hilton Chicago Downtown River North - Chicago - Lobby
Embassy Suites by Hilton Chicago Downtown River North
Near North Side
8.3Very good(2990)
Free Wi-Fi
Pool
C$ 276+
Check availability
SpringHill Suites by Marriott Chicago O'Hare - Chicago - Patio
SpringHill Suites by Marriott Chicago O'Hare
Norwood Park
8.2Very good(1586)
Airport shuttle
Free Wi-Fi
Pool
Pet friendly
C$ 193+
Check availability
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites
Near North Side
8.6Very good(2024)
Free Wi-Fi
Pool
Pet friendly
C$ 247+
Check availability
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Near North Side
7.9Good(3608)
Pool
Pet friendly
C$ 320+
Check availability
Hampton Inn & Suites Chicago-Downtown - Chicago - Lobby
Hampton Inn & Suites Chicago-Downtown
Near North Side
8.6Very good(2621)
Free Wi-Fi
Pool
Pet friendly
C$ 299+
Check availability
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
Near North Side
9.2Wonderful(2167)
Free Wi-Fi
Pool
Pet friendly
Spa
C$ 618+
Check availability
Best Western River North Hotel - Chicago - Balcony
Best Western River North Hotel
Near North Side
7.3Good(2995)
Free Wi-Fi
Pool
C$ 210+
Check availability
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel
O'Hare
8.1Very good(1366)
Airport shuttle
Pool
C$ 262+
Check availability
Radisson Blu Aqua Hotel, Chicago, IL - Chicago - Building
Radisson Blu Aqua Hotel, Chicago, IL
Downtown
7.9Good(2537)
Pool
Pet friendly
C$ 390+
Check availability
Homewood Suites by Hilton Chicago - Downtown - Chicago - Lounge
Homewood Suites by Hilton Chicago - Downtown
Near North Side
8.4Very good(2962)
Free Wi-Fi
Pool
Pet friendly
C$ 261+
Check availability
Sheraton Grand Chicago Riverwalk - Chicago - Living room
Sheraton Grand Chicago Riverwalk
Near North Side
8.3Very good(2214)
Free Wi-Fi
Pool
Pet friendly
C$ 430+
Check availability
The Wade - Chicago - Lobby
The Wade
Near North Side
8.0Very good(557)
Pool
Pet friendly
C$ 249+
Check availability
Loews Chicago Hotel - Chicago - Bedroom
Loews Chicago Hotel
Near North Side
9.0Wonderful(2130)
Free Wi-Fi
Pool
Pet friendly
Spa
C$ 514+
Check availability
Booking Insights

KAYAK’s insights for hotels with a pool in Chicago

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Chicago with confidence.

How much does a hotel room with a pool in Chicago cost?

The average price for a hotel with a pool in Chicago is C$ 330 but this can vary depending on the season, the star rating of the hotel and when you’ve booked. In the last 7 days, the cheapest price found on KAYAK was C$ 200.

Which month has the cheapest rates for hotels with a pool?

Hotels with a pool in Chicago are cheapest in September, with an average rate of C$ 110. On the other hand, they are at their most expensive in October, where the average price is C$ 1,305.

What is the cheapest day of the week to book a hotel with a pool in Chicago?

The lowest prices can usually be found on Thursday, where the average nightly price is C$ 110. The most expensive night is generally Monday, where the average price is C$ 407.

How much is a hotel with a pool in Chicago for tonight?

The best deal for a 3-star hotel with a pool room in Chicago found by KAYAK users in the last 3 days was C$ 181, while a 4-star hotel with a pool the lowest price was C$ 189. The cheapest room found overall was for C$ 138.

How much is a hotel with a pool in Chicago for this weekend?

The cheapest hotel with a pool room in Chicago for the upcoming weekend found on KAYAK in the last 3 days was for C$ 270 per night. For the same dates, 3-star hotel with a pool rooms have been found for as low as C$ 205 per night and 4-star hotel with a pool rooms from C$ 312 per night.

How early should you book a hotel with a pool in Chicago?

Book at least 24 days before your stay begins to get the best price for your Chicago hotel with a pool.

Find deals

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

Lowest hotel price

September
October
C$ 353
C$ 252
C$ 122
Cheapest month to stay with an average 74% drop in price.
Most expensive month to stay with an average 204% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.
The cheapest hotel with a pool room rate in the last 7 days

KAYAK's top tips for finding Chicago hotel with a pool deals

  • Prices for hotels with a pool in Chicago are cheaper in the low season, which is in September and February.
  • Pool room prices can vary depending on different factors. However, generally, rooms cost less on a Thursday. The most expensive night for a stay is Monday.
  • The cheapest hotel with a pool room in Chicago found on KAYAK in the last 2 weeks was C$ 183. The most expensive cost C$ 682.

FAQs about Chicago hotels with a pool

Where to stay in a hotel with a pool in Chicago?

Our map will help you find the perfect place to stay in Chicago by showing you the exact location of each hotel.

Everything you need to know for your stay in Chicago