Chicago Hotels With a Pool

Search and compare hundreds of travel sites at once for hotels with a pool in Chicago, Illinois

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Booking Insights
Recommended by KAYAK

Best Chicago hotels with a pool

Go to map

Search by stars

2+ stars3+ stars4+ stars5 stars

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

$24 - $198$198 - $371$371 - $544$544 - $717$717+ per night

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

Most recommended Chicago hotels with a pool

Show all
The Langham Chicago - Chicago - Lounge
The Langham Chicago
Near North Side
9.5Wonderful(926)
Free Wi-Fi
Pool
Pet friendly
Spa
$723+
Check availability
The Peninsula Chicago - Chicago - Lobby
The Peninsula Chicago
Near North Side
9.4Wonderful(568)
Free Wi-Fi
Pool
Pet friendly
Spa
$881+
Check availability
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
Near North Side
9.1Wonderful(1428)
Free Wi-Fi
Pool
Pet friendly
$527+
Check availability
Loews Chicago Hotel - Chicago - Bedroom
Loews Chicago Hotel
Near North Side
9.1Wonderful(2099)
Free Wi-Fi
Pool
Pet friendly
Spa
$405+
Check availability
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
Near North Side
9.1Wonderful(2099)
Free Wi-Fi
Pool
Pet friendly
Spa
$588+
Check availability
Waldorf Astoria Chicago - Chicago - Balcony
Waldorf Astoria Chicago
Near North Side
8.9Very good(337)
Pool
Pet friendly
Spa
$891+
Check availability
JW Marriott Chicago - Chicago - Lounge
JW Marriott Chicago
Downtown
8.6Very good(468)
Pool
Spa
$523+
Check availability
Renaissance Chicago Downtown Hotel - Chicago - Building
Renaissance Chicago Downtown Hotel
Downtown
8.6Very good(676)
Free Wi-Fi
Pool
Pet friendly
Spa
$463+
Check availability
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North
Near North Side
8.5Very good(922)
Free Wi-Fi
Pool
Pet friendly
$324+
Check availability
Hampton Inn & Suites Chicago-Downtown - Chicago - Lobby
Hampton Inn & Suites Chicago-Downtown
Near North Side
8.5Very good(2530)
Free Wi-Fi
Pool
Pet friendly
$309+
Check availability
Hyatt Centric Chicago Magnificent Mile - Chicago - Restaurant
Hyatt Centric Chicago Magnificent Mile
Near North Side
8.5Very good(2218)
Free Wi-Fi
Pool
Pet friendly
$396+
Check availability
Hyatt Regency Mccormick Place - Chicago - Patio
Hyatt Regency Mccormick Place
Near South Side
8.5Very good(2839)
Free Wi-Fi
Pool
$433+
Check availability
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites
Near North Side
8.5Very good(1952)
Free Wi-Fi
Pool
Pet friendly
$308+
Check availability
Homewood Suites by Hilton Chicago - Downtown - Chicago - Lounge
Homewood Suites by Hilton Chicago - Downtown
Near North Side
8.3Very good(2821)
Free Wi-Fi
Pool
Pet friendly
$310+
Check availability
AC Hotels by Marriott Chicago Downtown - Chicago - Restaurant
AC Hotels by Marriott Chicago Downtown
Near North Side
8.3Very good(1425)
Free Wi-Fi
Pool
Pet friendly
$291+
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 $134, while a 4-star hotel with a pool the lowest price was $215. The cheapest room found overall was for $134.

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 $249 per night. For the same dates, 3-star hotel with a pool rooms have been found for as low as $134 per night and 4-star hotel with a pool rooms from $249 per night.

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

Book at least 58 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)

June
October
$181
$292
Cheapest month to stay with an average 43% drop in price.
Most expensive month to stay with an average 34% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

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 May.
  • Pool room prices can vary depending on different factors. However, generally rooms cost less on a Sunday. The most expensive night for a stay is Tuesday.
  • The cheapest hotel with a pool room in Chicago found on KAYAK in the last 2 weeks was $175. The most expensive cost $685.

FAQs about Chicago hotels with a pool

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

    On average, rooms in hotels with pools in Chicago cost $606. Depending on when you make your booking, when you book for, and other factors, it is possible to get better deals. The cheapest price booked on KAYAK in the last 3 days was $158.

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

Deals for hotels in Chicago that have a swimming pool. Search for hotels with a pool in Chicago. KAYAK searches hundreds of travel sites to help you find hotels with a pool and book the room that suits you best.

Not what you’re looking for? Find thousands of other hotels, flight deals, car rentals and package deals with KAYAK.