Sleepy Hollow Hotels, Chicago

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Check prices for these dates

Tonight
16 Oct - 17 Oct
Tomorrow
17 Oct - 18 Oct
This weekend
17 Oct - 19 Oct
Next weekend
24 Oct - 26 Oct

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

Outdoor pool, pool cabanas (surcharge), pool umbrellas
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
8.8 out of 10, Excellent, (2100)
"Great hotel"
The price is AU$287
includes taxes & fees
2 Nov - 3 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
Reception
River Hotel
River Hotel
4.0 star property
8.8 out of 10, Excellent, (4749)
"Staff friendly and helpful..and accommodations just right..great location! "
The price is AU$282
includes taxes & fees
29 Oct - 30 Oct
River Hotel
Reception
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4.0 star property
8.8 out of 10, Excellent, (3086)
"Great, clean hotel in perfect location "
The price is AU$196
includes taxes & fees
16 Nov - 17 Nov
Eurostars Magnificent Mile
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
9.4 out of 10, Exceptional, (2197)
"Great hotel "
The price is AU$339
includes taxes & fees
12 Nov - 13 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
Exterior
Hilton Chicago
Hilton Chicago
4.0 star property
8.4 out of 10, Very good, (2265)
"We loved this hotel it was beautiful and convenient . "
The price is AU$377
includes taxes & fees
9 Nov - 10 Nov
Hilton Chicago
Cocktail bar
Aloft Chicago Mag Mile
Aloft Chicago Mag Mile
3.0 star property
8.6 out of 10, Excellent, (2868)
"Had a great stay!"
The price is AU$249
includes taxes & fees
9 Nov - 10 Nov
Aloft Chicago Mag Mile
Banquet hall
Congress Plaza Hotel
Congress Plaza Hotel
3.5 star property
8.0 out of 10, Very good, (9441)
"Beautiful hotel!"
The price is AU$230
includes taxes & fees
2 Nov - 3 Nov
Congress Plaza Hotel
American cuisine
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 star property
9.0 out of 10, Wonderful, (1604)
"Great Hotel"
The price is AU$221
includes taxes & fees
16 Nov - 17 Nov
Crowne Plaza Chicago West Loop by IHG
Terrace/patio
citizenM Chicago Downtown
citizenM Chicago Downtown
4.0 star property
9.2 out of 10, Wonderful, (3957)
"Great place to stay. "
The price is AU$236
includes taxes & fees
9 Nov - 10 Nov
citizenM Chicago Downtown
Ballroom
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 star property
8.8 out of 10, Excellent, (3122)
"Our stay was great"
The price is AU$203
includes taxes & fees
16 Nov - 17 Nov
Hilton Chicago/Magnificent Mile Suites
Rooftop terrace
Best Western River North Hotel
Best Western River North Hotel
2.5 star property
7.8 out of 10, Good, (1028)
"Great stay"
The price is AU$182
includes taxes & fees
9 Nov - 10 Nov
Best Western River North Hotel
Lobby
Regal Inn - Chicago O'Hare Airport
Regal Inn - Chicago O'Hare Airport
2.0 star property
8.0 out of 10, Very good, (1011)
"Inexpensive, close to the airport, clean"
Regal Inn - Chicago O'Hare Airport
Cocktail bar
Freehand Chicago
Freehand Chicago
4.0 star property
8.0 out of 10, Very good, (2484)
"Great place"
The price is AU$147
includes taxes & fees
10 Nov - 11 Nov
Freehand Chicago
Lobby
Super 8 by Wyndham Chicago O'Hare Airport
Super 8 by Wyndham Chicago O'Hare Airport
3.5 star property
7.6 out of 10, Good, (1478)
"Budget rate rooms - decent price and decent place to sleep"
The price is AU$133
includes taxes & fees
19 Oct - 20 Oct
Super 8 by Wyndham Chicago O'Hare Airport
Exterior
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
8.4 out of 10, Very good, (4089)
"Clean room , staff were friendly, a lot of restaurants in the area."
The price is AU$254
includes taxes & fees
6 Nov - 7 Nov
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Exterior
Comfort Suites Chicago O'Hare Airport
Comfort Suites Chicago O'Hare Airport
3.0 star property
8.2 out of 10, Very good, (2669)
"Clean quiet and great location!"
The price is AU$132
includes taxes & fees
2 Nov - 3 Nov
Comfort Suites Chicago O'Hare Airport
Front of property – evening/night
Eaglewood Resort and Spa
Eaglewood Resort and Spa
4.0 star property
8.6 out of 10, Excellent, (1014)
"Beautiful property, reasonably priced for an end of season stay. "
The price is AU$238
includes taxes & fees
20 Oct - 21 Oct
Eaglewood Resort and Spa
Front of property
Hotel Riu Plaza Chicago
Hotel Riu Plaza Chicago
4.0 star property
9.4 out of 10, Exceptional, (2608)
"Great place to stay "
The price is AU$298
includes taxes & fees
9 Nov - 10 Nov
Hotel Riu Plaza Chicago
Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe
The Whitehall Hotel, BW Premier Collection
The Whitehall Hotel, BW Premier Collection
3.5 star property
8.2 out of 10, Very good, (3663)
"Great location , good breakfast"
The price is AU$170
includes taxes & fees
16 Nov - 17 Nov
The Whitehall Hotel, BW Premier Collection
Exterior
FOUND Hotel Chicago River North
FOUND Hotel Chicago River North
2.0 star property
8.2 out of 10, Very good, (277)
"Perfect location! Tons of restaurants and shopping nearby! "
The price is AU$138
includes taxes & fees
10 Nov - 11 Nov
FOUND Hotel Chicago River North
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

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 which includes a river or creek

The Loop

Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.

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

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

10/10 Excellent
"It was a good launching spot to go down to the Chicago Marathon. "
Paula 2-night trip
Posted 11 hours ago
DoubleTree by Hilton Chicago - Magnificent Mile

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.

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