Find Hotels with a Pool in Winnetka, IL

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Winnetka Hotels with a Pool

Top Winnetka Hotels with a Pool

The Wade
1 bedroom, premium bedding, down comforters, pillowtop beds

The Wade

4.5 star property
8.2 out of 10, Very Good, (1187)
"Awesome place to stay"
The price is ￥22,226
￥26,090 total
includes taxes & fees
Sep 4 - Sep 5
The Wade
Hyatt Regency McCormick Place Chicago
Indoor pool

Hyatt Regency McCormick Place Chicago

4.0 star property
9.2 out of 10, Wonderful, (1001)
"Great place to stay especially with the price! "
The price is ￥29,291
￥37,842 total
includes taxes & fees
Aug 21 - Aug 22
Hyatt Regency McCormick Place Chicago
Sheraton Grand Chicago Riverwalk
Fitness facility

Sheraton Grand Chicago Riverwalk

4.0 star property
8.4 out of 10, Very Good, (1436)
"Awesome stay"
The price is ￥32,368
￥42,433 total
includes taxes & fees
Sep 1 - Sep 2
Sheraton Grand Chicago Riverwalk
Loews Chicago Hotel
Indoor pool

Loews Chicago Hotel

4.5 star property
9.4 out of 10, Exceptional, (1517)
"This is a nice hotel in a great neighborhood. "
The price is ￥29,412
￥39,214 total
includes taxes & fees
Sep 2 - Sep 3
Loews Chicago Hotel
Hilton Grand Vacations Club Chicago Magnificent Mile
Seasonal outdoor pool, sun loungers

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 star property
9.2 out of 10, Wonderful, (281)
" Great Stay!"
The price is ￥31,144
￥36,560 total
includes taxes & fees
Aug 25 - Aug 26
Hilton Grand Vacations Club Chicago Magnificent Mile
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Indoor pool

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4.0 star property
8.2 out of 10, Very Good, (2719)
"A+ hotel!"
The price is ￥25,000
￥33,686 total
includes taxes & fees
Aug 24 - Aug 25
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
Outdoor pool, sun loungers

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1987)
"Pool area and deck were great for the family, beds were comfortable, location is great."
The price is ￥22,347
￥26,234 total
includes taxes & fees
Aug 24 - Aug 25
DoubleTree by Hilton Chicago - Magnificent Mile
Radisson Blu Aqua Hotel Chicago
Indoor pool, seasonal outdoor pool, free cabanas, sun loungers

Radisson Blu Aqua Hotel Chicago

4.5 star property
8.4 out of 10, Very Good, (1623)
"Lovely hotel and in the most convenient location"
The price is ￥28,366
￥37,792 total
includes taxes & fees
Sep 2 - Sep 3
Radisson Blu Aqua Hotel Chicago
Aloft Chicago Mag Mile
Indoor pool, open 7:00 AM to 10:00 PM, sun loungers

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2793)
"We love our stay here !"
The price is ￥20,544
￥24,116 total
includes taxes & fees
Sep 1 - Sep 2
Aloft Chicago Mag Mile
Hyatt Centric Chicago Magnificent Mile
Indoor pool

Hyatt Centric Chicago Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (1020)
"Best place we have stayed in Chicago in a long time. "
The price is ￥23,500
￥31,926 total
includes taxes & fees
Aug 24 - Aug 25
Hyatt Centric Chicago Magnificent Mile
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.

Top Winnetka Hotel Reviews

The Wade

The Wade

10/10 Excellent
"Everything was great. Thanks for an awesome experience. "
veronica 2-night trip
Posted 7 hours ago
The Wade

Frequently asked questions

What are some accommodations with pools in Winnetka?
Congress Plaza Hotel: Hotel steps from State Street. Offers a full-service spa, an indoor pool, and a 24-hour fitness center. Palmer House a Hilton Hotel: Hotel, 4-minute walk from Michigan Avenue. Provides complimentary wired internet access, an indoor pool, and LCD televisions. Hilton Garden Inn Chicago Downtown/Magnificent Mile: Hotel, 4-minute walk from Michigan Avenue. Features full, an indoor pool, and flat-screen televisions. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 8-minute walk from Lake Michigan. Offers a 24-hour fitness center, an indoor pool, and flat-screen televisions. CitizenM Chicago Downtown: Hotel steps from Michigan Avenue. Provides 2 restaurants, an indoor pool, and a steam room.
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.