Hotels with Pool & Resorts in Winnetka from AU$225

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Check availability on Winnetka Hotels with Pool

Tonight
3 Oct - 4 Oct
Tomorrow
4 Oct - 5 Oct
This weekend
3 Oct - 5 Oct
Next weekend
10 Oct - 12 Oct

Best Winnetka Hotels with Pool

The Hoxton Chicago
Seasonal outdoor pool

The Hoxton Chicago

4.0 star property
9.0 out of 10, Wonderful, (1001)
"Beautiful hotel in a great location "
The price is AU$390
includes taxes & fees
26 Oct - 27 Oct
The Hoxton Chicago
Level Chicago Fulton Market
Executive lounge

Level Chicago Fulton Market

4.0 star property
9.2 out of 10, Wonderful, (312)
"Great place will return "
Level Chicago Fulton Market
Best Western River North Hotel
Indoor pool

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1017)
"Great stay"
The price is AU$225
includes taxes & fees
4 Nov - 5 Nov
Best Western River North Hotel
DoubleTree by Hilton Chicago - Magnificent Mile
Outdoor pool, pool cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (2076)
"Great hotel"
The price is AU$283
includes taxes & fees
2 Nov - 3 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
Palmer House a Hilton Hotel
Indoor pool

Palmer House a Hilton Hotel

4.0 star property
8.4 out of 10, Very good, (1994)
"Great property with great staff and amenities. "
The price is AU$351
includes taxes & fees
30 Oct - 31 Oct
Palmer House a Hilton Hotel
Level Chicago – Old Town
Seasonal outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (361)
"Great place to stay. Loved it!"
Level Chicago – Old Town
Hilton Grand Vacations Club Chicago Magnificent Mile
Seasonal outdoor pool, pool loungers

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 star property
9.2 out of 10, Wonderful, (300)
"Love the stay"
The price is AU$381
includes taxes & fees
30 Oct - 31 Oct
Hilton Grand Vacations Club Chicago Magnificent Mile
Hyatt House Chicago West Loop
Indoor pool

Hyatt House Chicago West Loop

3.5 star property
8.8 out of 10, Excellent, (1045)
"Great location near lots of restaurants. "
The price is AU$345
includes taxes & fees
2 Nov - 3 Nov
Hyatt House Chicago West Loop
Hyatt Centric Chicago Magnificent Mile
Indoor pool

Hyatt Centric Chicago Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (1031)
"Great place to stay"
The price is AU$368
includes taxes & fees
30 Oct - 31 Oct
Hyatt Centric Chicago Magnificent Mile
Aloft Chicago Mag Mile
Indoor pool, open 7:00 AM to 10:00 PM, pool loungers

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2844)
"Had a great stay!"
The price is AU$256
includes taxes & fees
2 Nov - 3 Nov
Aloft Chicago Mag 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.
View all properties

Top Winnetka Hotel Reviews

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

10/10 Excellent
"Very comfortable stay, excellent location. "
Andrea 3-night trip
Posted 13 hours ago
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Frequently asked questions

What are some accommodation options with pools in Winnetka?
Congress Plaza Hotel: Hotel, 4-minute walk from Michigan Avenue. Provides full, an indoor pool and flat-screen televisions. Freehand Chicago: Hotel, 4-minute walk from Michigan Avenue. Features complimentary high-speed (wired) Internet access, an indoor pool and LCD televisions. Embassy Suites by Hilton Chicago Downtown River North: Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool and a steam room. Hilton Chicago/Magnificent Mile Suites: Hotel steps from State Street. Offers a full-service spa, an indoor pool and a 24-hour fitness centre. CitizenM Chicago Downtown: Hotel, 8-minute walk from Lake Michigan. Offers a 24-hour fitness centre, an indoor pool and flat-screen televisions.
What is there to see and do in Winnetka?
Explore places such as Lake Michigan while you're in Winnetka. Make a point to visit attractions such as Chocolate Box.
When is the best time to book a hotel with a pool in Winnetka?
You may want to consider accommodation that offers an outdoor pool if you're planning to visit Winnetka in the hottest months of July, August or June, when the average temperature is 21°C. Accommodation 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 -1°C.
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 might not have very many public transport options, so consider renting a car to explore more.

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