Chicago Hotels with a Pool

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Recommended by KAYAK

Best Chicago hotels with a pool

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Most recommended Chicago hotels with a pool

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Aloft Chicago Mag Mile - Chicago - Lounge
Aloft Chicago Mag Mile
Near North Side
8.2Very Good(1647)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
£220+
Check availability
Homewood Suites by Hilton Chicago - Downtown - Chicago - Lounge
Homewood Suites by Hilton Chicago - Downtown
Near North Side
8.3Very Good(2863)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
£227+
Check availability
Hampton Inn & Suites Chicago-Downtown - Chicago - Lobby
Hampton Inn & Suites Chicago-Downtown
Near North Side
8.6Very Good(2563)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
£233+
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(2805)
Free Wi-Fi
Pool
Air conditioning
£238+
Check availability
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North
Near North Side
8.5Very Good(967)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
£260+
Check availability
Hyatt Centric Chicago Magnificent Mile - Chicago - Bedroom
Hyatt Centric Chicago Magnificent Mile
Near North Side
8.5Very Good(2224)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
£334+
Check availability
Loews Chicago Hotel - Chicago - Bedroom
Loews Chicago Hotel
Near North Side
9.0Wonderful(2120)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
£349+
Check availability
Hyatt Regency Mccormick Place - Chicago - Patio
Hyatt Regency Mccormick Place
Near South Side
8.5Very Good(2866)
Free Wi-Fi
Pool
Air conditioning
£352+
Check availability
JW Marriott Chicago - Chicago - Lounge
JW Marriott Chicago
Downtown
8.6Very Good(473)
Pool
Air conditioning
£375+
Check availability
Renaissance Chicago Downtown Hotel - Chicago - Building
Renaissance Chicago Downtown Hotel
Downtown
8.7Very Good(682)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
£382+
Check availability
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
Near North Side
9.1Wonderful(2121)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
£418+
Check availability
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
Near North Side
9.0Wonderful(1450)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
£439+
Check availability
The Langham Chicago - Chicago - Lounge
The Langham Chicago
Near North Side
9.4Wonderful(932)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
£627+
Check availability
Waldorf Astoria Chicago - Chicago - Balcony
Waldorf Astoria Chicago
Near North Side
9.0Wonderful(339)
Pool
Pet-friendly
Air conditioning
£680+
Check availability
The Peninsula Chicago - Chicago - Lobby
The Peninsula Chicago
Near North Side
9.4Wonderful(572)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
£689+
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 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 £158, while a 4-star hotel with a pool the lowest price was £182. The cheapest room found overall was for £158.

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 £100 per night. For the same dates, 3-star hotel with a pool rooms have been found for as low as £97 per night and 4-star hotel with a pool rooms from £156 per night.
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Good to know

Low season

High season

Lowest hotel price

June
July
£79
Cheapest month to stay with an average 64% drop in price.
Most expensive month to stay with an average 67% rise in price.
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 June and October.
  • The cheapest hotel with a pool room in Chicago found on KAYAK in the last 2 weeks was £399. The most expensive cost £399.

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

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