Sleepy Hollow Hotels, Chicago

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Tonight
19 Sept - 20 Sept
Tomorrow
20 Sept - 21 Sept
This weekend
19 Sept - 21 Sept
Next weekend
26 Sept - 28 Sept

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4713 Cheap Hotels in Sleepy Hollow - Specials, Reviews, & Last Minute Deals

River Hotel
Reception

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4684)
"Friendly staff and great location!"
The price is NZ$312
includes taxes & fees
2 Oct - 3 Oct
River Hotel
DoubleTree by Hilton Chicago - Magnificent Mile
Outdoor pool, pool loungers

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (2049)
"We had a great stay, we will be visiting again"
The price is NZ$366
includes taxes & fees
19 Oct - 20 Oct
DoubleTree by Hilton Chicago - Magnificent Mile
Eurostars Magnificent Mile
Reception

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (3056)
"Super nice rooms, friendly staff, great location. Would recommend this Hotel to anyone visiting the downtown area of Chicago "
The price is NZ$351
includes taxes & fees
22 Sept - 23 Sept
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, (2149)
"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
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (3815)
"Great place to stay for a quick trip!"
The price is NZ$312
includes taxes & fees
22 Sept - 23 Sept
citizenM Chicago Downtown
Aloft Chicago Mag Mile
Meeting facility

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2836)
"Great place to stay!"
The price is NZ$337
includes taxes & fees
22 Sept - 23 Sept
Aloft Chicago Mag Mile
Hilton Chicago
Exterior

Hilton Chicago

4.0 star property
8.4 out of 10, Very good, (2211)
"Amazing stay and great location…"
The price is NZ$417
includes taxes & fees
26 Sept - 27 Sept
Hilton Chicago
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, (3920)
"Excellent central location and local dining options. "
The price is NZ$366
includes taxes & fees
22 Sept - 23 Sept
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (9226)
"Very nice place to stay and friendly staff! "
Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites
Ballroom

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2901)
"Great hotel at a great value "
The price is NZ$321
includes taxes & fees
20 Oct - 21 Oct
Hilton Chicago/Magnificent Mile Suites
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very good, (2340)
"Nice place to stay!"
The price is NZ$290
includes taxes & fees
1 Oct - 2 Oct
Freehand Chicago
Best Western River North Hotel
Rooftop terrace

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1031)
"It was a great stay"
The price is NZ$280
includes taxes & fees
22 Sept - 23 Sept
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, (245)
"Lovely hotel."
The price is NZ$218
includes taxes & fees
28 Sept - 29 Sept
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, (2452)
"Nice hotel with amazing breakfasts and location."
The price is NZ$368
includes taxes & fees
22 Sept - 23 Sept
Hotel Riu Plaza Chicago
The Whitehall Hotel, BW Premier Collection
Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe

The Whitehall Hotel, BW Premier Collection

3.5 star property
8.2 out of 10, Very good, (3593)
"Staff were friendly and location was perfect."
The price is NZ$273
includes taxes & fees
22 Sept - 23 Sept
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, (1010)
"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, (1432)
"Great staff, clean room, shuttle to and from the airport."
The price is NZ$150
includes taxes & fees
24 Sept - 25 Sept
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, (2614)
"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 NZ$168
includes taxes & fees
5 Oct - 6 Oct
Comfort Suites Chicago O'Hare Airport
Hyatt Centric The Loop Chicago
Rooftop terrace

Hyatt Centric The Loop Chicago

4.0 star property
9.0 out of 10, Wonderful, (2132)
"Great place and really nice people "
The price is NZ$445
includes taxes & fees
21 Sept - 22 Sept
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, (2545)
"Very nice stay "
The price is NZ$365
includes taxes & fees
21 Sept - 22 Sept
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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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

River Hotel

River Hotel

10/10 Excellent
"Friendly staff and great location!"
Michael 1-night trip
Posted 3 days ago
River 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.