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Check prices for these dates

This weekend
19 Jun - 21 Jun
Next weekend
26 Jun - 28 Jun

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Our top choices for Sleepy Hollow hotels

Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Streeterville, 14.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,551 reviews)
"The location was very convenient"
United States
Jeffrey
The price is 5.730.055 ₫
7.719.630 ₫ total
includes taxes & fees
30 Jun - 1 Jul
Sable at Navy Pier Chicago, Curio Collection by Hilton
Breakfast and dinner served

Omni Chicago Hotel

Omni Chicago Hotel
4.5 star property
Streeterville, 13.2 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,811 reviews)
"All around great property and a wonderful location"
United States
Bruce
The price is 3.346.842 ₫
4.854.918 ₫ total
includes taxes & fees
1 Jul - 2 Jul
Omni Chicago Hotel
Lobby

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11.9 km from Sleepy Hollow
8.0 out of 10, Very good, (10,283 reviews)
"Great stay!"
United States
Daniel
The price is 3.588.358 ₫
4.266.198 ₫ total
includes taxes & fees
29 Jun - 30 Jun
Congress Plaza Hotel
Reception

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Theatre District, 12.1 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,510 reviews)
"Beautiful place to stay."
United States
Charles Otto
The price is 5.048.363 ₫
6.784.194 ₫ total
includes taxes & fees
6 Jul - 7 Jul
Palmer House a Hilton Hotel
Front of property

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13.3 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,455 reviews)
"Clean room, great breakfast and close to everything we needed"
United States
Kyle
The price is 4.207.752 ₫
5.752.431 ₫ total
includes taxes & fees
6 Jul - 7 Jul
Hotel Riu Plaza Chicago
Lobby

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 11.8 km from Sleepy Hollow
7.4 out of 10, Good, (2,649 reviews)
"Great location and helpful staff."
United States
Ming
The price is 3.555.796 ₫
4.227.486 ₫ total
includes taxes & fees
1 Jul - 2 Jul
Travelodge by Wyndham Downtown Chicago
Interior detail

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Theatre District, 12.2 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1,102 reviews)
"Good location, friendly staff"
United Kingdom
Philip
The price is 3.649.670 ₫
5.119.447 ₫ total
includes taxes & fees
6 Jul - 7 Jul
Staypineapple, An Iconic Hotel, The Loop
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,393 reviews)
"Nice Hotel, rooms are clean , the best for us was the location, i would recommend"
United States
Sergio
The price is 4.630.560 ₫
6.432.006 ₫ total
includes taxes & fees
1 Jul - 2 Jul
Swissotel - Chicago
Lobby

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Theatre District, 12.2 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,257 reviews)
"Awesome place"
United States
Mellany
The price is 3.417.178 ₫
4.865.664 ₫ total
includes taxes & fees
6 Jul - 7 Jul
Silversmith Hotel Chicago Downtown
View from property

The Blackstone, Autograph Collection

The Blackstone, Autograph Collection
4.0 star property
The Loop, 11.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,012 reviews)
"Great location, clean hotel, and very accommodating staff."
United States
Neydee
The price is 4.289.056 ₫
5.871.720 ₫ total
includes taxes & fees
30 Jun - 1 Jul
The Blackstone, Autograph Collection
2 restaurants; breakfast, lunch and dinner served

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,744 reviews)
"Great location!"
United States
William
The price is 4.897.343 ₫
6.594.649 ₫ total
includes taxes & fees
1 Jul - 2 Jul
LondonHouse Chicago, Curio Collection by Hilton
Reception hall

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,657 reviews)
"Had an amazing stay here!"
United States
Audrey
The price is 3.999.120 ₫
4.754.554 ₫ total
includes taxes & fees
1 Jul - 2 Jul
Eurostars Magnificent Mile
Restaurant

Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
The Loop, 11.5 km from Sleepy Hollow
8.2 out of 10, Very good, (2,734 reviews)
"Nice place to stay at"
United States
Tammy
The price is 3.136.152 ₫
3.728.569 ₫ total
includes taxes & fees
1 Jul - 2 Jul
Best Western Grant Park Hotel
Exterior

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Streeterville, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (4,431 reviews)
"Great stay!"
United States
Avradita
The price is 4.117.252 ₫
4.894.976 ₫ total
includes taxes & fees
5 Jul - 6 Jul
Hilton Chicago/Magnificent Mile Suites
Lobby

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Gold Coast, 13.9 km from Sleepy Hollow
8.2 out of 10, Very good, (1,611 reviews)
"Very good location, breakfast is fantastic, dinner and bar are great."
United States
Zhiwen
The price is 4.112.516 ₫
4.889.187 ₫ total
includes taxes & fees
29 Jun - 30 Jun
The Chicago Hotel Collection Ambassador Gold Coast
2 bars/lounges

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 13.2 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,668 reviews)
"Location was great"
United States
Pamela
The price is 5.240.952 ₫
7.169.445 ₫ total
includes taxes & fees
2 Jul - 3 Jul
Sheraton Grand Chicago Riverwalk
2 bars/lounges

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,521 reviews)
"Staff was great."
United States
Marianne
The price is 5.346.192 ₫
7.294.566 ₫ total
includes taxes & fees
2 Jul - 3 Jul
Hyatt Regency Chicago
Pool

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
The Loop, 11.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,047 reviews)
"Great room and view. Clean, near by Grant park, great staff."
United States
Kimberly
The price is 3.861.782 ₫
4.591.272 ₫ total
includes taxes & fees
6 Jul - 7 Jul
Hilton Garden Inn Chicago Downtown South Loop
Presidential Suite, 1 Bedroom, Non Smoking | Premium bedding, in-room safe, desk, blackout curtains

Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown
4.0 star property
River North, 13.1 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,599 reviews)
"Great stay"
United States
Matt
The price is 3.709.710 ₫
5.192.671 ₫ total
includes taxes & fees
1 Jul - 2 Jul
Hotel 55 Chicago Downtown
Executive lounge

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 12.9 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,203 reviews)
"Location is excellent!"
United States
Michele
The price is 5.369.871 ₫
7.322.336 ₫ total
includes taxes & fees
6 Jul - 7 Jul
Fairmont Chicago at Millennium Park
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

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Magnificent Mile

Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.

The Loop

Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops and acclaimed art galleries.

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.

Panoramic view of Lincoln Park and the Chicago skyline.

Lincoln Park

Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.

Top Sleepy Hollow Hotel Reviews

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"The staff at the hotel was incredibly helpful and friendly. The property was clean and centrally located for all the touristy experiences! Fulton Market District, Millennium Park were all within walking distance. If you need recommendations for dinner or sightseeing, the staff is super helpful! The brekafast buffet is worth every penny! If ever in the area again, we would definitely book again."
Bridget 4-night trip
Posted less than an hour ago
Crowne Plaza Chicago West Loop by IHG

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?
Douglas Park, Hawthorne Works Museum and Jedlica Performing Arts Center are just a few of the places to visit in and around Sleepy Hollow. When you're sightseeing in Chicago, Los Globos and Balzekas Museum of Lithuanian Culture are also worth a stop.