Stinson Memorial Library Anna Illinois Listed on the National Register Funded by Anna businessman Robert Burns Stinson, designed by Walter Burley Griffin who studied under Frank Lloyd Wright.

Find Hotels with a Pool in Winnetka, IL

Q: What are some accommodations with pools in Winnetka?

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 Chicago/Magnificent Mile Suites : Hotel steps from State Street. Provides a full-service spa, an indoor pool, and a 24-hour fitness center. Palmer House a Hilton Hotel : Hotel, 2-minute walk from State Street. Offers a snack bar/deli, a pool, and buffet. Club Quarters Hotel Wacker at Michigan, Chicago : Hotel, 4-minute walk from State Street. Features 2 restaurants, an indoor pool, and a health club. Silversmith Hotel Chicago Downtown : Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool, and a sauna.

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Our top choices for Winnetka hotels with a pool

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

Aloft Chicago Mag Mile

Downtown Chicago

lynne

$81 nightly

Jan 4 - Jan 5, 2026

Total with taxes and fees

Indoor pool, open 5:00 AM to 11:00 PM, sun loungers

voco Chicago Downtown - Riverwalk by IHG

Downtown Chicago

Kelly

$105 nightly

Dec 14 - Dec 15

Total with taxes and fees

Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

HANNAH

$71 nightly

Jan 5 - Jan 6, 2026

Total with taxes and fees

Hyatt Centric Chicago Magnificent Mile

Downtown Chicago

Hannah

$123 nightly

Jan 3 - Jan 4, 2026

Total with taxes and fees

Palmer House a Hilton Hotel

Downtown Chicago

Luis

$136 nightly

Dec 21 - Dec 22

Total with taxes and fees

Outdoor pool, cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

Alan

$89 nightly

Dec 21 - Dec 22

Total with taxes and fees

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

MARINA

$103 nightly

Dec 23 - Dec 24

Total with taxes and fees

Holiday Inn Chicago Dwtn - The Mart by IHG

Downtown Chicago

Kyan

$98 nightly

Dec 25 - Dec 26

Total with taxes and fees

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Top Winnetka Hotel Reviews

The Royal Sonesta Chicago Downtown

10/10 Excellent

"Courteous staff"

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"This is a great place to stay if you’re visiting Chicago! Right in the heart of downtown. Within walking distance to Millennial Park and all the shops on Michigan Avenue. Only 35 minutes from O’Hare. The staff were courteous and the hotel is beautiful! I would definitely stay here again!"

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent

"Everything was prefect. My only gripe was the heat was not heating as it should on 80 degrees. It was 20 degrees outside everyday. Other than that i will definitely return for another stay.. staff and Valetn were very professional and accommodating...10 star stay..."

Frequently asked questions

What are some accommodations with pools in Winnetka?

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 Chicago/Magnificent Mile Suites: Hotel steps from State Street. Provides a full-service spa, an indoor pool, and a 24-hour fitness center. Palmer House a Hilton Hotel: Hotel, 2-minute walk from State Street. Offers a snack bar/deli, a pool, and buffet. Club Quarters Hotel Wacker at Michigan, Chicago: Hotel, 4-minute walk from State Street. Features 2 restaurants, an indoor pool, and a health club. Silversmith Hotel Chicago Downtown: Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool, and a sauna.

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.

Find Hotels with a Pool in Winnetka, IL

Upfront pricing

Treat yourself

Be picky

Check availability on Winnetka Hotels with a Pool

Our top choices for Winnetka hotels with a pool

Aloft Chicago Mag Mile

voco Chicago Downtown - Riverwalk by IHG

Hilton Garden Inn Chicago Downtown South Loop

Hyatt Centric Chicago Magnificent Mile

Palmer House a Hilton Hotel

DoubleTree by Hilton Chicago - Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Holiday Inn Chicago Dwtn - The Mart by IHG

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Homewood Suites by Hilton Chicago Downtown South Loop

Top Winnetka Hotel Reviews

The Royal Sonesta Chicago Downtown

Palmer House a Hilton Hotel

Club Quarters Hotel Wacker at Michigan, Chicago

Crowne Plaza Chicago West Loop by IHG

InterContinental Chicago Magnificent Mile by IHG

Embassy Suites by Hilton Chicago Downtown River North

The Whitehall Hotel, BW Premier Collection

Hilton Chicago/Magnificent Mile Suites

Silversmith Hotel Chicago Downtown

Frequently asked questions

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