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14 Oct - 15 Oct
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15 Oct - 16 Oct
This weekend
17 Oct - 19 Oct
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24 Oct - 26 Oct

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Top Trending Hotels Near Sleepy Hollow, Chicago

Outdoor pool, pool cabanas (surcharge), pool umbrellas
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
8.8 out of 10, Excellent, (2091)
"Great hotel"
The price is Rp2.637.944
Rp3.096.681 total
includes taxes & fees
5 Nov - 6 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
Reception
River Hotel
River Hotel
4.0 star property
8.8 out of 10, Excellent, (4745)
"Staff friendly and helpful..and accommodations just right..great location! "
The price is Rp2.635.107
Rp3.093.352 total
includes taxes & fees
26 Oct - 27 Oct
River Hotel
Reception
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4.0 star property
9.0 out of 10, Wonderful, (3081)
"Very nice location and everything was a 10/10"
The price is Rp1.980.807
Rp2.325.269 total
includes taxes & fees
13 Nov - 14 Nov
Eurostars Magnificent Mile
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
9.4 out of 10, Exceptional, (2186)
"Great hotel "
The price is Rp2.638.422
Rp3.661.555 total
includes taxes & fees
9 Nov - 10 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
Exterior
Hilton Chicago
Hilton Chicago
4.0 star property
8.4 out of 10, Very good, (2261)
"We loved this hotel it was beautiful and convenient . "
The price is Rp3.047.554
Rp4.063.852 total
includes taxes & fees
23 Oct - 24 Oct
Hilton Chicago
Cocktail bar
Aloft Chicago Mag Mile
Aloft Chicago Mag Mile
3.0 star property
8.6 out of 10, Excellent, (2866)
"Had a great stay!"
The price is Rp2.287.074
Rp2.684.796 total
includes taxes & fees
9 Nov - 10 Nov
Aloft Chicago Mag Mile
Banquet hall
Congress Plaza Hotel
Congress Plaza Hotel
3.5 star property
8.0 out of 10, Very good, (9413)
"Beautiful hotel!"
Congress Plaza Hotel
American cuisine
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 star property
9.0 out of 10, Wonderful, (1597)
"Great Hotel"
The price is Rp2.154.490
Rp2.529.155 total
includes taxes & fees
9 Nov - 10 Nov
Crowne Plaza Chicago West Loop by IHG
Terrace/patio
citizenM Chicago Downtown
citizenM Chicago Downtown
4.0 star property
9.2 out of 10, Wonderful, (3951)
"Great place to stay. "
The price is Rp2.169.265
Rp2.546.501 total
includes taxes & fees
9 Nov - 10 Nov
citizenM Chicago Downtown
Ballroom
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 star property
8.8 out of 10, Excellent, (3101)
"Our stay was great"
The price is Rp2.380.711
Rp2.794.717 total
includes taxes & fees
9 Nov - 10 Nov
Hilton Chicago/Magnificent Mile Suites
Rooftop terrace
Best Western River North Hotel
Best Western River North Hotel
2.5 star property
7.8 out of 10, Good, (1025)
"Great stay"
The price is Rp1.676.359
Rp1.967.712 total
includes taxes & fees
9 Nov - 10 Nov
Best Western River North Hotel
Lobby
Regal Inn - Chicago O'Hare Airport
Regal Inn - Chicago O'Hare Airport
2.0 star property
8.0 out of 10, Very good, (1009)
"Inexpensive, close to the airport, clean"
Regal Inn - Chicago O'Hare Airport
Cocktail bar
Freehand Chicago
Freehand Chicago
4.0 star property
8.0 out of 10, Very good, (2469)
"Great place"
The price is Rp1.327.497
Rp1.850.174 total
includes taxes & fees
10 Nov - 11 Nov
Freehand Chicago
Lobby
Super 8 by Wyndham Chicago O'Hare Airport
Super 8 by Wyndham Chicago O'Hare Airport
3.5 star property
7.6 out of 10, Good, (1476)
"Budget rate rooms - decent price and decent place to sleep"
The price is Rp1.267.605
Rp1.432.139 total
includes taxes & fees
5 Nov - 6 Nov
Super 8 by Wyndham Chicago O'Hare Airport
Exterior
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
8.4 out of 10, Very good, (4078)
"Clean room , staff were friendly, a lot of restaurants in the area."
The price is Rp2.803.323
Rp3.290.901 total
includes taxes & fees
9 Nov - 10 Nov
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Exterior
Comfort Suites Chicago O'Hare Airport
Comfort Suites Chicago O'Hare Airport
3.0 star property
8.2 out of 10, Very good, (2659)
"Clean quiet and great location!"
The price is Rp1.394.366
Rp1.589.299 total
includes taxes & fees
27 Oct - 28 Oct
Comfort Suites Chicago O'Hare Airport
Front of property – evening/night
Eaglewood Resort and Spa
Eaglewood Resort and Spa
4.0 star property
8.6 out of 10, Excellent, (1010)
"Beautiful property, reasonably priced for an end of season stay. "
The price is Rp1.908.864
Rp2.483.015 total
includes taxes & fees
16 Oct - 17 Oct
Eaglewood Resort and Spa
Front of property
Hotel Riu Plaza Chicago
Hotel Riu Plaza Chicago
4.0 star property
9.4 out of 10, Exceptional, (2596)
"Great place to stay "
The price is Rp2.344.148
Rp3.218.823 total
includes taxes & fees
9 Nov - 10 Nov
Hotel Riu Plaza Chicago
Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe
The Whitehall Hotel, BW Premier Collection
The Whitehall Hotel, BW Premier Collection
3.5 star property
8.2 out of 10, Very good, (3658)
"Great location , good breakfast"
The price is Rp1.624.817
Rp1.907.387 total
includes taxes & fees
11 Nov - 12 Nov
The Whitehall Hotel, BW Premier Collection
Exterior
FOUND Hotel Chicago River North
FOUND Hotel Chicago River North
2.0 star property
8.2 out of 10, Very good, (273)
"Perfect location! Tons of restaurants and shopping nearby! "
The price is Rp1.331.972
Rp1.563.602 total
includes taxes & fees
10 Nov - 11 Nov
FOUND Hotel Chicago River North
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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Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas for the activities you enjoy most.
Downtown Chicago featuring a city

Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Magnificent Mile - River North

Magnificent Mile

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

The Loop - Downtown featuring a river or creek

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

Chicago featuring a city and modern architecture

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Top Sleepy Hollow Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"BEAUTIFUL IS ALL I HAVE TO SAY. THANKS SECURITY, I HAD A SAFE FUN FILLED DAY. LMAOOOO. Can't wait to return. "
corrine 1-night trip
Posted 23 hours ago
Congress Plaza Hotel

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Frequently asked questions

What's it like in Sleepy Hollow?
Sleepy Hollow is a neighbourhood that travellers like for its restaurants.
If I need to cancel my hotel reservation in Sleepy Hollow, will I receive a refund?
Yes! The majority of hotel reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you have a non-refundable reservation, you may still be able to cancel and be given a refund within 24 hours of your booking. Put your dates in and click on "Search", then filter by "fully refundable" to view the top deals on offer in Sleepy Hollow.
What can I see and do in this Chicago neighbourhood?
Hawthorne Works Museum, Balzekas Museum of Lithuanian Culture and Wintrust Sports Complex are just a few of the places to visit in and around Sleepy Hollow. When you're sightseeing around the area, United Center and Bridgeport Art Center are a couple of other sights to visit.