Sleepy Hollow Hotels, Chicago

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19 Sept - 20 Sept
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20 Sept - 21 Sept
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19 Sept - 21 Sept
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26 Sept - 28 Sept

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4718 Cheap Hotels in Sleepy Hollow - Specials, Reviews, & Last Minute Deals

Our top choices for Sleepy Hollow hotels

Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2454)
"Nice hotel with amazing breakfasts and location."
The price is NZ$368
includes taxes & fees
22 Sept - 23 Sept
Hotel Riu Plaza Chicago
Loews Chicago O'Hare Hotel
Reception hall

Loews Chicago O'Hare Hotel

4.5 star property
9.4 out of 10, Exceptional, (1899)
"Conveniently located to many restaurants and venues"
The price is NZ$405
includes taxes & fees
3 Oct - 4 Oct
Loews Chicago O'Hare Hotel
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Exterior

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

4.0 star property
9.6 out of 10, Exceptional, (1026)
"Great stay"
The price is NZ$397
includes taxes & fees
22 Sept - 23 Sept
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
LondonHouse Chicago, Curio Collection by Hilton
Lobby

LondonHouse Chicago, Curio Collection by Hilton

4.5 star property
9.4 out of 10, Exceptional, (3356)
"Loved this hotel- best location and very nice staff. "
The price is NZ$477
includes taxes & fees
2 Oct - 3 Oct
LondonHouse Chicago, Curio Collection by Hilton
L7 Chicago by LOTTE
Exterior

L7 Chicago by LOTTE

4.5 star property
9.6 out of 10, Exceptional, (2978)
"Excellent location, staff was very friendly"
The price is NZ$519
includes taxes & fees
22 Sept - 23 Sept
L7 Chicago by LOTTE
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (3817)
"Great place to stay for a quick trip!"
The price is NZ$312
includes taxes & fees
22 Sept - 23 Sept
citizenM Chicago Downtown
The Royal Sonesta Chicago River North
Terrace/patio

The Royal Sonesta Chicago River North

4.5 star property
9.2 out of 10, Wonderful, (2136)
"Great location and great staff."
The price is NZ$471
includes taxes & fees
21 Sept - 22 Sept
The Royal Sonesta Chicago River North
Thompson Chicago, by Hyatt
Restaurant

Thompson Chicago, by Hyatt

4.5 star property
9.2 out of 10, Wonderful, (1235)
"I’ve stayed here twice and had a positive experience both times."
The price is NZ$469
includes taxes & fees
19 Oct - 20 Oct
Thompson Chicago, by Hyatt
Silversmith Hotel Chicago Downtown
Lobby

Silversmith Hotel Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (1987)
"Great room and close to attractions "
Silversmith Hotel Chicago Downtown
Claridge House
Cocktail bar

Claridge House

4.0 star property
9.0 out of 10, Wonderful, (1373)
"We had a great stay"
The price is NZ$317
includes taxes & fees
21 Sept - 22 Sept
Claridge House
Kimpton Gray Hotel by IHG
Argentinean cuisine

Kimpton Gray Hotel by IHG

4.5 star property
9.2 out of 10, Wonderful, (1008)
"Amazing stay"
The price is NZ$505
includes taxes & fees
3 Oct - 4 Oct
Kimpton Gray Hotel by IHG
Swissotel - Chicago
Reception

Swissotel - Chicago

4.5 star property
9.0 out of 10, Wonderful, (2771)
"The hotel was in a great location. "
The price is NZ$435
includes taxes & fees
21 Sept - 22 Sept
Swissotel - Chicago
Omni Chicago Hotel
Breakfast and dinner served

Omni Chicago Hotel

4.5 star property
9.2 out of 10, Wonderful, (1577)
"Great stay!"
The price is NZ$523
includes taxes & fees
2 Oct - 3 Oct
Omni Chicago Hotel
Loews Chicago Hotel
Exterior

Loews Chicago Hotel

4.5 star property
9.4 out of 10, Exceptional, (1549)
"Great location, clean rooms , friendly staff amazing modern design , great to stay with family."
The price is NZ$591
includes taxes & fees
21 Sept - 22 Sept
Loews Chicago Hotel
Sofitel Chicago Magnificent Mile
Exterior

Sofitel Chicago Magnificent Mile

4.5 star property
9.4 out of 10, Exceptional, (2132)
"Nice Stay."
The price is NZ$587
includes taxes & fees
1 Oct - 2 Oct
Sofitel Chicago 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, (2151)
"Great place to stay!"
The price is NZ$479
includes taxes & fees
19 Oct - 20 Oct
Sable at Navy Pier Chicago, Curio Collection by Hilton
The Royal Sonesta Chicago Downtown
Exterior

The Royal Sonesta Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (2934)
"Wonderful property with wonderful staff will definitely stay here again. "
The price is NZ$511
includes taxes & fees
19 Oct - 20 Oct
The Royal Sonesta Chicago Downtown
Pendry Chicago
View from property

Pendry Chicago

4.5 star property
9.4 out of 10, Exceptional, (1088)
"Awesome hotel!"
The price is NZ$569
includes taxes & fees
2 Oct - 3 Oct
Pendry Chicago
Club Quarters Hotel, Central Loop, Chicago
Breakfast, lunch and dinner served

Club Quarters Hotel, Central Loop, Chicago

4.0 star property
8.8 out of 10, Excellent, (3356)
"Very good place to stay"
The price is NZ$282
includes taxes & fees
2 Oct - 3 Oct
Club Quarters Hotel, Central Loop, Chicago
Eaglewood Resort and Spa
Front of property – evening/night

Eaglewood Resort and Spa

4.0 star property
8.6 out of 10, Excellent, (1018)
"Great location for a staycation "
The price is NZ$230
includes taxes & fees
28 Sept - 29 Sept
Eaglewood Resort and Spa
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.
View all properties

Our guide on 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

5 out of top 10 points of interest in this area

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

An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.

The Loop - Downtown which includes 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 showing 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

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

10/10 Excellent
"This is a beautiful hotel and so conveniently located - easy to walk to museums and the Mag Mile"
amy 1-night trip
Posted 6 hours ago
Palmer House a Hilton Hotel

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 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?

Places you might want to visit in the area around Sleepy Hollow include Hawthorne Works Museum and Balzekas Museum of Lithuanian Culture. When you're sightseeing around the area, United Center and Bridgeport Art Center are a couple of other sights to visit.