Hotels with Swimming Pool in Winnetka, Chicago

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Check availability on Winnetka Hotels with Swimming Pool

Our top choices for Winnetka hotels with a pool

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,914 reviews)
The price is P6,205
P7,284 total
includes taxes & fees
Mar 22 - Mar 23
Hilton Chicago/Magnificent Mile Suites

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very Good, (1,718 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 P7,707
P9,048 total
includes taxes & fees
Mar 18 - Mar 19
The Wade

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,136 reviews)
  • cleanliness
    Splash into the city at this downtown hotel with a sleek indoor pool, stylish loungers, and a vibrant atmosphere to match.
The price is P6,453
P7,575 total
includes taxes & fees
Mar 22 - Mar 23
Aloft Chicago Mag Mile

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,104 reviews)
  • cleanliness
    Indoor pool oasis at upscale Michigan Avenue aparthotel offers year-round swimming enjoyment.
The price is P7,060
P10,041 total
includes taxes & fees
Mar 19 - Mar 20
Sentral Michigan Avenue

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,349 reviews)
  • cleanliness
    Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.
The price is P6,320
P7,419 total
includes taxes & fees
Mar 22 - Mar 23
DoubleTree by Hilton Chicago - Magnificent Mile

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Take a dip in the seasonal rooftop pool while sipping craft cocktails at this urban Chicago retreat.
The price is P9,088
P12,422 total
includes taxes & fees
Mar 22 - Mar 23
The Hoxton Chicago

Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Splash into pure relaxation at this downtown hotel's indoor pool with loungers and fitness center access.
The price is P11,412
P15,189 total
includes taxes & fees
Mar 20 - Mar 21
Renaissance Chicago Downtown Hotel

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (4,392 reviews)
  • cleanliness
    Make a splash at this downtown Chicago hotel with an indoor pool, fitness center, and stunning city views from each room.
The price is P6,055
P7,108 total
includes taxes & fees
Mar 24 - Mar 25
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,086 reviews)
  • cleanliness
    Splash into serenity at this Michigan Avenue retreat with a sparkling indoor pool, hot tub haven, and 24-hour fitness center.
The price is P7,648
P10,731 total
includes taxes & fees
Mar 22 - Mar 23
Hyatt Centric Chicago Magnificent Mile

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, (1,902 reviews)
  • cleanliness
    Dive into downtown luxury with a rejuvenating pool experience close to Chicago landmarks.
The price is P7,055
P8,282 total
includes taxes & fees
Apr 13 - Apr 14
Hilton Garden Inn 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.

Choose what matters most at hotels with a pool in Winnetka

Top Winnetka Hotel Reviews

Frequently asked questions

What are some accommodations with pools in Winnetka?
Congress Plaza Hotel: Hotel, 4-minute walk from Michigan Avenue. Provides full, an indoor pool, and flat-screen televisions. Hotel Riu Plaza Chicago: Hotel, 2-minute walk from Michigan Avenue. Features flat-screen televisions and an indoor pool. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 12-minute walk from Millennium Park. Offers 2 restaurants, an indoor pool, and a health club. Hilton Chicago/Magnificent Mile Suites: Hotel, 3-minute walk from Michigan Avenue. Provides a snack bar/deli, an indoor pool, and complimentary wireless internet access. Hilton Chicago O'Hare Airport: Hotel, 8-minute walk from Lake Michigan. Offers a 24-hour fitness center, an indoor pool, and flat-screen televisions.
What is there to see and do in Winnetka?
Explore places like Lake Michigan while you're in Winnetka. Make a point to visit attractions like Chocolate Box.
When is the best time to book a hotel with a pool in Winnetka?
You may want to consider an accommodation that offers an outdoor pool if you will be visiting Winnetka in the hottest months of July, August, or June when the average temperature is 70°F. Lodging with an indoor pool may be what you want if you visit during the coldest months of January, February, or December when the average temp is 30°F.
What's the best way to travel around Winnetka?
Knowing the transportation options in Winnetka can help you enjoy the area beyond your hotel pool. To see more of the surrounding area, hop aboard a train at Winnetka Station or Winnetka Indian Hill Station. Winnetka may not have many public transit choices so consider renting a car to explore more.

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