Hotels in Sleepy Hollow, Chicago

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Check prices for these dates

Tonight
27 Oct - 28 Oct
Tomorrow
28 Oct - 29 Oct
This weekend
31 Oct - 2 Nov
Next weekend
7 Nov - 9 Nov

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Top 10 Hotels in Sleepy Hollow, Chicago

Reception
River Hotel
River Hotel
4.0 star property
8.8 out of 10, Excellent, (4756)
"Great area at a good price. "
United States
Laura
The price is RM474
RM556 total
includes taxes & fees
9 Nov - 10 Nov
River Hotel
Reception
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4.0 star property
8.8 out of 10, Excellent, (3090)
"Excellent stay, close to everything and the staff was super nice "
United States
Kieata
The price is RM456
RM535 total
includes taxes & fees
25 Nov - 26 Nov
Eurostars Magnificent Mile
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, (2113)
"Great stay "
United States
Melinda
The price is RM503
RM591 total
includes taxes & fees
23 Nov - 24 Nov
DoubleTree by Hilton Chicago - 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, (2226)
"Rooms were clean with a great view of the lake and the city "
United States
Nathan
The price is RM416
RM632 total
includes taxes & fees
25 Nov - 26 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
Cocktail bar
Aloft Chicago Mag Mile
Aloft Chicago Mag Mile
3.0 star property
8.6 out of 10, Excellent, (2875)
"Had a great stay!"
United States
Josh
The price is RM456
RM535 total
includes taxes & fees
23 Nov - 24 Nov
Aloft Chicago Mag Mile
Exterior
Hilton Chicago
Hilton Chicago
4.0 star property
8.4 out of 10, Very good, (2274)
"Staff was wonderful, property was clean and welcoming. Great amenities for families and great location."
United States
Stephen
The price is RM479
RM687 total
includes taxes & fees
24 Nov - 25 Nov
Hilton Chicago
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, (1632)
"Great Hotel"
United States
Cesar
The price is RM431
RM506 total
includes taxes & fees
26 Nov - 27 Nov
Crowne Plaza Chicago West Loop by IHG
Terrace/patio
citizenM Chicago Downtown
citizenM Chicago Downtown
4.0 star property
9.4 out of 10, Exceptional, (4008)
"Great place to stay. "
United States
sherry
The price is RM463
RM544 total
includes taxes & fees
30 Oct - 31 Oct
citizenM Chicago Downtown
Banquet hall
Congress Plaza Hotel
Congress Plaza Hotel
3.5 star property
8.0 out of 10, Very good, (9608)
"Area is great and walkable distance to touring areas. "
United States
Alejandro
The price is RM718
RM843 total
includes taxes & fees
2 Nov - 3 Nov
Congress Plaza Hotel
Rooftop terrace
Best Western River North Hotel
Best Western River North Hotel
2.5 star property
7.8 out of 10, Good, (1009)
"Great stay"
Australia
Bart
The price is RM427
RM501 total
includes taxes & fees
9 Nov - 10 Nov
Best Western River North Hotel
Ballroom
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 star property
9.0 out of 10, Wonderful, (3183)
"Overall it was a great place to stay."
United States
Edward
The price is RM463
RM544 total
includes taxes & fees
16 Nov - 17 Nov
Hilton Chicago/Magnificent Mile Suites
Cocktail bar
Freehand Chicago
Freehand Chicago
4.0 star property
8.0 out of 10, Very good, (2531)
"Very accessible location and amazing staff. "
United States
Fatima
The price is RM338
RM472 total
includes taxes & fees
10 Nov - 11 Nov
Freehand Chicago
Lobby
Regal Inn - Chicago O'Hare Airport
Regal Inn - Chicago O'Hare Airport
2.0 star property
8.0 out of 10, Very good, (1010)
"Inexpensive, close to the airport, clean"
United States
Jay
Regal Inn - 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, (4116)
"This hotel had a great location to shopping and several enjoyable restaurants."
United States
laura
The price is RM488
RM573 total
includes taxes & fees
24 Nov - 25 Nov
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Front of property
Hotel Riu Plaza Chicago
Hotel Riu Plaza Chicago
4.0 star property
9.4 out of 10, Exceptional, (2669)
"Great place to stay "
United States
Larry William
The price is RM454
RM652 total
includes taxes & fees
25 Nov - 26 Nov
Hotel Riu Plaza 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, (1476)
"I liked that people where super helpful, had its own shuttle and indoor pool"
Canada
Valeria
The price is RM304
RM344 total
includes taxes & fees
26 Nov - 27 Nov
Super 8 by Wyndham Chicago O'Hare Airport
Exterior
Comfort Suites Chicago O'Hare Airport
Comfort Suites Chicago O'Hare Airport
3.0 star property
8.2 out of 10, Very good, (2712)
"Clean quiet and great location!"
United States
Cyrus
The price is RM319
RM364 total
includes taxes & fees
9 Nov - 10 Nov
Comfort Suites Chicago O'Hare Airport
Exterior
FOUND Hotel Chicago River North
FOUND Hotel Chicago River North
2.0 star property
8.2 out of 10, Very good, (288)
"Perfect location! Tons of restaurants and shopping nearby! "
United States
MaryJane
The price is RM321
RM377 total
includes taxes & fees
11 Nov - 12 Nov
FOUND Hotel Chicago River North
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, (3661)
"Excellent location, old style hotel with an independent feel. "
United States
Jose
The price is RM360
RM422 total
includes taxes & fees
24 Nov - 25 Nov
The Whitehall Hotel, BW Premier Collection
Front of property – evening/night
Eaglewood Resort and Spa
Eaglewood Resort and Spa
4.0 star property
8.8 out of 10, Excellent, (1025)
"Beautiful property, reasonably priced for an end of season stay. "
United States
ANDREW
The price is RM470
RM614 total
includes taxes & fees
9 Nov - 10 Nov
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.
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Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas for the activities you enjoy most.
Downtown Chicago which includes 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 featuring 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.

Lincoln Park showing modern architecture and a city

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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"From the moment we walked in the security was very friendly and helpful the first front desk attendant was amazing her name was Jasmine she was incredibly sweet helped us the best she could when we came back to do an early check-in the second person who helped us was incredibly rude service was terrible she basically told us we were liars, didn't explain all my charges just told me to sign when I asked for an explanation she seemed bothered by it overall the experience was great minus that second front desk attendant unfortunately I did not get her name because when I asked she walked off.. Bed was comfortable view was amazing. . "
Sarah 4-night trip
Posted 2 days ago
Congress Plaza Hotel

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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.