Sleepy Hollow Hotels near Chicago

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Sep 26 - Sep 27
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Sep 27 - Sep 28
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Sep 26 - Sep 28
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Oct 3 - Oct 5

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Top Trending Hotels Near Sleepy Hollow, Chicago

River Hotel
Reception

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4710)
"Friendly staff and great location!"
The price is P11,562
P13,573 total
includes taxes & fees
Sep 28 - Sep 29
River Hotel
DoubleTree by Hilton Chicago - Magnificent Mile
Outdoor pool, cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (2074)
"Staff was very friendly, rooms were cleaned daily, and the onsite restaurant was fantastic!"
The price is P10,644
P12,495 total
includes taxes & fees
Oct 19 - Oct 20
DoubleTree by Hilton Chicago - Magnificent Mile
Eurostars Magnificent Mile
Reception

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (3075)
"Perfect location, walkable to many restaurants and shops"
The price is P10,145
P11,909 total
includes taxes & fees
Oct 27 - Oct 28
Eurostars Magnificent Mile
Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2167)
"I enjoyed my stay cant wait to go back. "
The price is P12,504
P16,363 total
includes taxes & fees
Oct 19 - Oct 20
Sable at Navy Pier Chicago, Curio Collection by Hilton
Aloft Chicago Mag Mile
Meeting facility

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2854)
"Had a great stay!"
The price is P10,226
P12,004 total
includes taxes & fees
Oct 2 - Oct 3
Aloft Chicago Mag Mile
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (3867)
"Great stay"
The price is P10,568
P12,406 total
includes taxes & fees
Sep 28 - Sep 29
citizenM Chicago Downtown
Hilton Chicago
Exterior

Hilton Chicago

4.0 star property
8.4 out of 10, Very Good, (2218)
"Amazing stay and great location…"
The price is P11,555
P15,270 total
includes taxes & fees
Oct 23 - Oct 24
Hilton Chicago
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very Good, (9313)
"The staff was top notch, the bed so comfortable, just a great overall stay"
Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites
Ballroom

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2978)
"Enjoyed our stay"
The price is P9,334
P10,957 total
includes taxes & fees
Oct 20 - Oct 21
Hilton Chicago/Magnificent Mile Suites
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Exterior

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
8.4 out of 10, Very Good, (3985)
"Excellent central location and local dining options. "
The price is P11,197
P13,145 total
includes taxes & fees
Oct 5 - Oct 6
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very Good, (2390)
"Location was excellent would stay there again"
The price is P7,501
P11,534 total
includes taxes & fees
Sep 30 - Oct 1
Freehand Chicago
Best Western River North Hotel
Rooftop terrace

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1037)
"It was a great stay"
The price is P8,939
P10,494 total
includes taxes & fees
Oct 2 - Oct 3
Best Western River North Hotel
FOUND Hotel Chicago River North
Exterior

FOUND Hotel Chicago River North

2.0 star property
8.2 out of 10, Very Good, (256)
"Lovely hotel."
The price is P6,657
P7,814 total
includes taxes & fees
Oct 2 - Oct 3
FOUND Hotel Chicago River North
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2482)
"Nice hotel with amazing breakfasts and location."
The price is P9,873
P13,227 total
includes taxes & fees
Oct 1 - Oct 2
Hotel Riu Plaza Chicago
The Whitehall Hotel, BW Premier Collection
Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe

The Whitehall Hotel, BW Premier Collection

3.5 star property
8.2 out of 10, Very Good, (3626)
"Staff were friendly and location was perfect."
The price is P8,295
P9,737 total
includes taxes & fees
Oct 20 - Oct 21
The Whitehall Hotel, BW Premier Collection
Regal Inn - Chicago O'Hare Airport
Lobby

Regal Inn - Chicago O'Hare Airport

2.0 star property
8.0 out of 10, Very Good, (1013)
"Inexpensive, close to the airport, clean"
Regal Inn - Chicago O'Hare Airport
Super 8 by Wyndham Chicago O'Hare Airport
Lobby

Super 8 by Wyndham Chicago O'Hare Airport

3.5 star property
7.6 out of 10, Good, (1448)
"Great staff, clean room, shuttle to and from the airport."
The price is P4,914
P5,552 total
includes taxes & fees
Sep 29 - Sep 30
Super 8 by Wyndham Chicago O'Hare Airport
Comfort Suites Chicago O'Hare Airport
Exterior

Comfort Suites Chicago O'Hare Airport

3.0 star property
8.2 out of 10, Very Good, (2640)
"I liked the fact that breakfast was complimentary, the staff was super friendly and courteous and there was accessible shopping areas nearby."
The price is P5,062
P5,770 total
includes taxes & fees
Oct 1 - Oct 2
Comfort Suites Chicago O'Hare Airport
Hyatt Centric The Loop Chicago
Exterior

Hyatt Centric The Loop Chicago

4.0 star property
9.0 out of 10, Wonderful, (2154)
"Great place and really nice people "
The price is P12,490
P14,661 total
includes taxes & fees
Oct 3 - Oct 4
Hyatt Centric The Loop Chicago
La Quinta Inn & Suites by Wyndham Chicago Downtown
Exterior

La Quinta Inn & Suites by Wyndham Chicago Downtown

3.0 star property
8.6 out of 10, Excellent, (2558)
"Very nice hotel"
The price is P10,981
P13,914 total
includes taxes & fees
Oct 2 - Oct 3
La Quinta Inn & Suites by Wyndham Chicago Downtown
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 and neighborhoods for the activities you enjoy most.
Downtown Chicago which includes 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

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

The Loop - Downtown showing 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.

Lincoln Park featuring modern architecture and a city

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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Great stay friendly staff"
Melissa 2-night trip
Posted 2 days ago
Hilton Chicago/Magnificent Mile Suites

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What's it like in Sleepy Hollow?

Sleepy Hollow is a neighborhood that travelers 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 room reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel and receive a refund within a 24-hour period of your booking. Put your dates in and click on "Search", then you can use the "fully refundable" filter to get the best deals available in Sleepy Hollow.

Where can I learn more about changing or cancelling my trip to Sleepy Hollow?

For more information about picking new dates or cancelling your trip to Sleepy Hollow, click here.

What can I see and do in this Chicago neighborhood?

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.