Hotels with Pool & Resorts in Chicago from AU$179

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Check availability on Chicago Hotels with Pool

Our top choices for Chicago hotels with a pool

Indoor pool, open 7:00 AM to 10:00 PM, pool loungers

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,232 reviews)
  • cleanliness
    Splash into the city at this city centre hotel with a sleek indoor pool, stylish loungers, and a vibrant atmosphere to match.
The price is AU$179
includes taxes & fees
10 May - 11 May
Aloft Chicago Mag Mile
Indoor pool

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,783 reviews)
  • cleanliness
    Soak in relaxation at this historic Chicago hotel's indoor pool with spa amenities nearby.
The price is AU$254
includes taxes & fees
25 May - 26 May
Hilton Chicago
Outdoor pool, pool cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,463 reviews)
  • cleanliness
    Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.
The price is AU$241
includes taxes & fees
25 May - 26 May
DoubleTree by Hilton Chicago - Magnificent Mile
Indoor pool

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,833 reviews)
  • cleanliness
    Float away at this stunning luxury hotel with an indoor pool overlooking Lake Michigan and the city's iconic skyline.
The price is AU$212
includes taxes & fees
10 May - 11 May
The Wade
Pool

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,990 reviews)
  • cleanliness
    Dive into city centre luxury with a rejuvenating pool experience close to Chicago landmarks.
The price is AU$207
includes taxes & fees
26 May - 27 May
Hilton Garden Inn Chicago Downtown South Loop
Seasonal outdoor pool

Level Chicago - River North

Level Chicago - River North
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (989 reviews)
  • cleanliness
    Summer splashes and cityscape views await at this Chicago hotel's seasonal rooftop pool.
The price is AU$355
includes taxes & fees
21 May - 22 May
Level Chicago - River North
Fitness facility

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,627 reviews)
  • cleanliness
    Riverside hotel offers waterfront relaxation with indoor pool near Michigan Avenue.
The price is AU$402
includes taxes & fees
25 May - 26 May
Sheraton Grand Chicago Riverwalk
Indoor pool

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (3,048 reviews)
  • cleanliness
    World-class indoor pool in city centre offers lap swimming and family fun at this luxury hotel.
The price is AU$375
includes taxes & fees
26 May - 27 May
InterContinental Chicago Magnificent Mile by IHG
Seasonal outdoor pool

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,011 reviews)
  • cleanliness
    Take a dip in the seasonal rooftop pool while sipping craft cocktails at this urban Chicago retreat.
The price is AU$349
includes taxes & fees
10 May - 11 May
The Hoxton Chicago
Indoor pool

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (5,934 reviews)
  • cleanliness
    Slip into a holiday state of mind at Chicago's urban retreat with a sparkling indoor pool.
The price is AU$268
includes taxes & fees
25 May - 26 May
Embassy Suites by Hilton Chicago Downtown River North
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.
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Choose what matters most at hotels with a pool in Chicago

Breakfast included
Spa pool

Hotels with pools and free breakfast in Chicago

Exterior
Hilton Chicago

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2783)
The price is AU$254
includes taxes & fees
25 May - 26 May
Hilton Chicago
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Hotels with pools and spa pools in Chicago

Exterior
Hilton Chicago

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2783)
The price is AU$254
includes taxes & fees
25 May - 26 May
Hilton Chicago
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4-star hotels with pools in Chicago

Indoor pool
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (3048)
The price is AU$375
includes taxes & fees
26 May - 27 May
InterContinental Chicago Magnificent Mile by IHG
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.
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Top Chicago Hotel Reviews

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

10/10 Excellent
"great location"
Julie 2-night trip
Posted 13 hours ago
Hotel Felix River North/Magnificent Mile

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 141 places to stay with pools. While you're visiting, you can explore attractions such as Navy Pier and Wrigley Field, 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. Hilton Garden Inn Chicago Downtown South Loop: Hotel, 13-minute walk from Lake Michigan. Offers a snack bar/deli, a pool and complimentary wireless Internet access. Holiday Inn & Suites Chicago - Downtown by IHG: Hotel, 10-minute walk from University of Illinois Chicago. Provides a snack bar/deli, a seasonal outdoor pool and complimentary wireless Internet access. Embassy Suites by Hilton Chicago O'Hare Rosemont: Hotel, 3-minute walk from Donald E. Stephens Convention Center. Features buffet, an indoor pool and a 24-hour fitness centre. Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG: Hotel, 5-minute walk from Donald E. Stephens Convention Center. Offers 3 restaurants, an indoor pool and complimentary wireless Internet access.
How many hotels with pools should I expect to find in Chicago?
Expedia's 141 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 Navy Pier, Wrigley Field and Naval Base Great Lakes 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.