Find Hotels with a Pool in Winnetka, IL from CA $203

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Check availability on Winnetka Hotels with a Pool

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Top Winnetka Hotels with a Pool

The Wade

4.5 star property
8.2 out of 10, Very good, (1055)
"My room had tile damage in the bathroom. Also it was a bit dusty. The overall area was clean around the property. The
pool
is amazing and the area was clean. The room service was great. I’ll definitely come back again. "
Kristina
The price is CA $250
CA $294 total
includes taxes & fees
Aug 4 - Aug 5
The Wade

Hyatt Regency McCormick Place Chicago

4.0 star property
9.0 out of 10, Wonderful, (1002)
"My room was amazing. Two of the walls were floor to ceiling glass with a great view. There were two chaise"
Susan
The price is CA $243
CA $318 total
includes taxes & fees
Jul 7 - Jul 8
Hyatt Regency McCormick Place Chicago

Sheraton Grand Chicago Riverwalk

4.0 star property
8.4 out of 10, Very good, (1377)
"Suzanne went above and beyond to make our stay so special! She was my go to person that made our time there so awesome. Such a thoughtful, detailed and caring person. Robert at security and Sam at check in were also amazing and so helpful. The general staff we encountered was amazing and so polite. We enjoyed the
indoor pool
and the bar lounge was so convenient to hang out for drinks and catch up with friends. We can’t wait to return."
Francesca
The price is CA $317
CA $413 total
includes taxes & fees
Jul 24 - Jul 25
Sheraton Grand Chicago Riverwalk

Loews Chicago Hotel

4.5 star property
9.4 out of 10, Exceptional, (1477)
"Amazing location and excellent rooms. The
pool
was perfect for a good workout. "
Diana Catalina
The price is CA $230
CA $313 total
includes taxes & fees
Jul 7 - Jul 8
Loews Chicago Hotel

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (2714)
"Nice property. Onsite breakfast is great with kids! Warm
pool
! "
Kimberly
The price is CA $272
CA $319 total
includes taxes & fees
Jul 9 - Jul 10
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1899)
"The property was nice and clean. We weren’t able to utilize the
pool
due to maintenance. This was a little frustrating due to the fact that was one of the reason we solely chose this hotel and then we were never told until we asked if we could utilize it. We also were told we had free breakfast which was not true. Last but not least, we had banging every night that kept us awake that was coming from the construction next to our room. This was also a little frustrating because my son is autistic...
Emilee
The price is CA $250
CA $293 total
includes taxes & fees
Jul 13 - Jul 14
DoubleTree by Hilton Chicago - Magnificent Mile

Radisson Blu Aqua Hotel Chicago

4.5 star property
8.4 out of 10, Very good, (1491)
"Great location!!! Nice views, great food, loved the
outdoor pool
and comfortable beds. "
amy
The price is CA $288
CA $380 total
includes taxes & fees
Aug 4 - Aug 5
Radisson Blu Aqua Hotel Chicago

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2748)
"I stayed here the week leading up to Thanksgiving 2024. Great location to many of the sites in Chicago. Was able to walk everywhere. The staff were friendly, and always willing to help out or answer any questions. The gym was great, got in a good workout & loved the views. I opted for the breakfast package which was nice being able to get something to eat before going out for the day. The lobby had lots of seating and games/
pool
table which kept my little one entertained and busy. We would...
Kristin
The price is CA $203
CA $238 total
includes taxes & fees
Jul 7 - Jul 8
Aloft Chicago Mag Mile

Hyatt Centric Chicago Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (1025)
"Great, friendly staff the updated rooms & the
pool
/whirlpool were top notch. Exceptional value and would highly recommend it to families/others looking for a good Chicago “tourist-friendly”, but high quality hotel. "
Nicholas
The price is CA $271
CA $358 total
includes taxes & fees
Jul 10 - Jul 11
Hyatt Centric Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3.0 star property
8.8 out of 10, Excellent, (1456)
"It was a perfect, we loved our rooms, we had amazing drinks at the copper fox, the kids loved the
pool
. The staff was lovely, the valet parking was easy. Thank you!"
Julia
The price is CA $245
CA $287 total
includes taxes & fees
Jul 7 - Jul 8
Courtyard by Marriott 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.

Frequently asked questions

What are some accommodations with pools in Winnetka?
InterContinental Chicago Magnificent Mile by IHG: Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool, and a steam room. Hilton Chicago/Magnificent Mile Suites: Hotel, 4-minute walk from Michigan Avenue. Features full, an indoor pool, and flat-screen televisions. Congress Plaza Hotel: Hotel located near Allstate Arena. Offers daily, an indoor pool, and free self parking. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 8-minute walk from Lake Michigan. Features 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.