Find hotels with pools in Sleepy Hollow, Chicago from $89

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Check availability on Sleepy Hollow Hotels with a Pool

Tonight
Nov 25 - Nov 26
Tomorrow
Nov 26 - Nov 27
This weekend
Nov 28 - Nov 30
Next weekend
Dec 5 - Dec 7

Top Sleepy Hollow Hotels with a Pool

Indoor pool, open 5:00 AM to 11:00 PM, sun loungers
voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3398)
"Great hotel!!"
United States
Deja
$103 nightly
The price is $121
Dec 14 - Dec 15
Total with taxes and fees
voco Chicago Downtown - Riverwalk by IHG
Indoor pool
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (5297)
"Nice staff A lot of restaurants and stores near the hotel Good breakfast "
United States
Viviana Velazquez
$87 nightly
The price is $102
Dec 21 - Dec 22
Total with taxes and fees
Embassy Suites by Hilton Chicago Downtown River North
Indoor pool
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (2096)
"Great place to stay."
United States
Aaron
$128 nightly
The price is $145
Dec 21 - Dec 22
Total with taxes and fees
Palmer House a Hilton Hotel
Indoor pool
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1042)
"Great Hotel!"
United States
Wendy
$123 nightly
The price is $144
Dec 7 - Dec 8
Total with taxes and fees
Hyatt Centric Chicago Magnificent Mile
Indoor pool
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2018)
"Great hotel."
United States
Mario
$95 nightly
The price is $112
Dec 22 - Dec 23
Total with taxes and fees
Holiday Inn Chicago Dwtn - The Mart by IHG
Indoor pool
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (4199)
"Great location. "
United States
Rodger
$75 nightly
The price is $89
Dec 10 - Dec 11
Total with taxes and fees
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Indoor pool, open 7:00 AM to 10:00 PM, sun loungers
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2935)
"Great location!!"
United States
sarah e
$90 nightly
The price is $106
Dec 7 - Dec 8
Total with taxes and fees
Aloft Chicago Mag Mile
Indoor pool
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2273)
"My favorite place to stay when I go to Chicago! "
United States
Sara
$130 nightly
The price is $152
Nov 26 - Nov 27
Total with taxes and fees
The Royal Sonesta Chicago River North
Pool
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, (1728)
"Clean room, great hot tub."
United States
SHARON
$79 nightly
The price is $93
Dec 21 - Dec 22
Total with taxes and fees
Hilton Garden Inn Chicago Downtown South Loop
Outdoor pool, cabanas (surcharge), pool umbrellas
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2153)
"Great stay "
United States
Melinda
$98 nightly
The price is $115
Dec 7 - Dec 8
Total with taxes and fees
DoubleTree by Hilton 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.
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Top Sleepy Hollow Hotel Reviews

Hilton Chicago

Hilton Chicago

10/10 Excellent
"No toiletries in the bathroom past shampoo and conditioner! Beautiful grounds and clean! Great location to downtown and stadiums"
Krista 2-night trip
Posted 9 hours ago
Hilton Chicago

Frequently asked questions

What are some accommodations with pools in Sleepy Hollow?
Embassy Suites by Hilton Chicago Downtown River North: Hotel, 4-minute walk from Michigan Avenue. Features full, an indoor pool, and flat-screen televisions. Palmer House a Hilton Hotel: Hotel steps from State Street. Offers a full-service spa, an indoor pool, and a 24-hour fitness center. Hilton Chicago/Magnificent Mile Suites: Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool, and a sauna. CitizenM Chicago Downtown: Hotel, 4-minute walk from State Street. Offers 2 restaurants, an indoor pool, and a health club. Warwick Allerton - Chicago: 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 Sleepy Hollow?
Explore places like Michigan Avenue, Wrigley Field, and United Center while you're in the area. Make a point to visit attractions like Millennium Park and Garfield Park Conservatory.
When is the best time to book a hotel with a pool in Sleepy Hollow?
You may want to consider an accommodation that has an outdoor pool if you're planning to visit in the warmest 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 come to town during the coldest months of January, February, or December when the average temperature is 31°F.

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