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Top Trending Hotels Near Sleepy Hollow, Chicago

The Godfrey Hotel Chicago

4.5 star property
River North, 12.8 km from Sleepy Hollow
8.6 out of 10, Excellent, (1910)
"Awesome staff and great location "
United States
Luis C
The price is ₹7,884
₹11,369 total
includes taxes & fees
29 Dec - 30 Dec
The Godfrey Hotel Chicago

Aloft Chicago Downtown River North

3.5 star property
River North, 12.6 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1156)
"Modern vibes, a lot to see, eat and do at walking distance, spotless room and very comfy bed. Very friendly staff. Definitely would stay there again."
United States
Cristina
The price is ₹9,449
₹11,092 total
includes taxes & fees
21 Dec - 22 Dec
Aloft Chicago Downtown River North

The Wade

4.5 star property
Streeterville, 13.8 km from Sleepy Hollow
8.4 out of 10, Very good, (1501)
"Great location, walkable to so many area attractions. Would definitely stay here again. "
United States
Debbie
The price is ₹9,088
₹10,668 total
includes taxes & fees
6 Jan - 7 Jan 2026
The Wade

Club Quarters Hotel Wacker at Michigan, Chicago

4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (1950)
"A good place for stay "
United States
Julio
The price is ₹7,484
₹8,785 total
includes taxes & fees
7 Dec - 8 Dec
Club Quarters Hotel Wacker at Michigan, Chicago

The Royal Sonesta Chicago River North

4.5 star property
River North, 12.8 km from Sleepy Hollow
9.2 out of 10, Wonderful, (2297)
"Great place - stayed with extended family. Lounge areas and amenities met everyone’s needs "
United States
Elizabeth
The price is ₹9,260
₹13,750 total
includes taxes & fees
7 Dec - 8 Dec
The Royal Sonesta Chicago River North

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
Streeterville, 13.5 km from Sleepy Hollow
7.6 out of 10, Good, (1176)
"The room was spacious and clean and it was a good value."
United States
Dj
The Chicago Hotel Collection - Magnificent Mile

voco Chicago Downtown - Riverwalk by IHG

3.5 star property
River North, 12 km from Sleepy Hollow
8.8 out of 10, Excellent, (3433)
"Great hotel"
United States
Clara
The price is ₹9,868
₹11,584 total
includes taxes & fees
7 Dec - 8 Dec
voco Chicago Downtown - Riverwalk by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 star property
Magnificent Mile, 13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (2605)
"Great hotel, best location, nice and very helpful staff "
United States
Carlos
The price is ₹12,959
₹18,092 total
includes taxes & fees
4 Jan - 5 Jan 2026
InterContinental Chicago Magnificent Mile by IHG

Arlo Chicago

4.0 star property
Theatre District, 12.5 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1873)
"Great location, friendly staff, lovely rooms! "
United Kingdom
Oliver
The price is ₹10,327
₹14,809 total
includes taxes & fees
4 Jan - 5 Jan 2026
Arlo Chicago

ACME Hotel Company

3.5 star property
River North, 12.9 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1900)
"Lived up to expectations. Bathroom was really nice. Would stay here again."
United States
Nolan
The price is ₹8,828
₹10,363 total
includes taxes & fees
7 Dec - 8 Dec
ACME Hotel Company

Moxy Chicago Downtown

3.0 star property
River North, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (848)
"Great place to stay"
United States
Mason
The price is ₹10,122
₹11,883 total
includes taxes & fees
2 Jan - 3 Jan 2026
Moxy Chicago Downtown

Sofitel Chicago Magnificent Mile

4.5 star property
13.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2245)
"The staff, food, and service were great. "
United States
Randy
The price is ₹15,305
₹20,607 total
includes taxes & fees
22 Dec - 23 Dec
Sofitel Chicago Magnificent Mile

Hilton Chicago/Magnificent Mile Suites

3.5 star property
Streeterville, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3434)
"Great hotel located in nice area."
United States
Robert
The price is ₹9,446
₹11,088 total
includes taxes & fees
14 Dec - 15 Dec
Hilton Chicago/Magnificent Mile Suites

Virgin Hotels Chicago

4.5 star property
Theatre District, 12.5 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1416)
"Excellent hotel the rooms are awesome "
United States
Devita
The price is ₹13,086
₹18,426 total
includes taxes & fees
17 Dec - 18 Dec
Virgin Hotels Chicago

Omni Chicago Hotel

4.5 star property
Magnificent Mile, 13.3 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1625)
"Excellent Hotel, fantastic room suite, and TV.s and view. And the staff was amazing. "
United States
Michael
The price is ₹16,480
₹21,988 total
includes taxes & fees
23 Dec - 24 Dec
Omni Chicago Hotel

Ivy Boutique Hotel

4.5 star property
Streeterville, 13.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (1032)
"Clean room, nice amenities (especially like the rain shower), very centrally located, and friendly staff. "
United States
Kathleen
The price is ₹9,169
₹10,764 total
includes taxes & fees
6 Jan - 7 Jan 2026
Ivy Boutique Hotel

Central Loop Hotel

4.0 star property
Theatre District, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (1921)
"Very clean and well maintained room, comfortable bed, and great location!"
United States
Rebecca
The price is ₹7,484
₹8,785 total
includes taxes & fees
7 Dec - 8 Dec
Central Loop Hotel

LondonHouse Chicago, Curio Collection by Hilton

4.5 star property
The Loop, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3421)
"Great Hotel!"
United States
Siranush
The price is ₹11,733
₹13,774 total
includes taxes & fees
4 Jan - 5 Jan 2026
LondonHouse Chicago, Curio Collection by Hilton

Hotel Saint Clair- Magnificent Mile

4.0 star property
Streeterville, 13.3 km from Sleepy Hollow
8.2 out of 10, Very good, (1778)
"Great stay in a great area."
United States
Giselle
Hotel Saint Clair- Magnificent Mile

AC Hotels by Marriott Chicago Downtown

4.0 star property
River North, 13.1 km from Sleepy Hollow
8.8 out of 10, Excellent, (1003)
"Helpful staff Great location for attractions"
United States
Youngjun
The price is ₹9,359
₹10,987 total
includes taxes & fees
25 Dec - 26 Dec
AC Hotels by Marriott 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.

Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas for the activities you enjoy most.

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

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

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.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).

Top Sleepy Hollow Hotel Reviews

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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.