Sleepy Hollow Hotels, Chicago

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Check prices for these dates

Tonight
7 Jul - 8 Jul
Tomorrow
8 Jul - 9 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

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4654 Cheap Hotels in Sleepy Hollow - Specials, Reviews, & Last Minute Deals

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, (2049)
"Amazing property clean comfy bedding and wonderful views"
The price is NZ$418
includes taxes & fees
13 July - 14 July
Sable at Navy Pier Chicago, Curio Collection by Hilton
Swissotel - Chicago
Front of property - evening/night

Swissotel - Chicago

4.5 star property
8.8 out of 10, Excellent, (2367)
"It was a great stay! "
The price is NZ$439
includes taxes & fees
10 July - 11 July
Swissotel - Chicago
Loews Chicago Hotel
Exterior

Loews Chicago Hotel

4.5 star property
9.4 out of 10, Exceptional, (1480)
"Great location and rooms "
The price is NZ$457
includes taxes & fees
8 July - 9 July
Loews Chicago 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, (1901)
"Nice location Room was clean and had everything we needed "
The price is NZ$356
includes taxes & fees
13 July - 14 July
DoubleTree by Hilton Chicago - Magnificent Mile
Radisson Blu Aqua Hotel Chicago
Indoor pool, seasonal outdoor pool, free pool cabanas, pool loungers

Radisson Blu Aqua Hotel Chicago

4.5 star property
8.4 out of 10, Very good, (1494)
"Great location and views from rooms were beautiful. "
The price is NZ$458
includes taxes & fees
4 Aug - 5 Aug
Radisson Blu Aqua Hotel Chicago
Fairmont Chicago at Millennium Park
Exterior

Fairmont Chicago at Millennium Park

4.5 star property
8.6 out of 10, Excellent, (1803)
"Great stay, great location and very polite staff "
The price is NZ$492
includes taxes & fees
7 Aug - 8 Aug
Fairmont Chicago at Millennium Park
Aloft Chicago Mag Mile
Exterior

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2754)
"Good location, comfortable bed, staff very nice and helpful!"
The price is NZ$308
includes taxes & fees
8 July - 9 July
Aloft Chicago Mag Mile
Ivy Boutique Hotel
Front of property

Ivy Boutique Hotel

4.5 star property
8.8 out of 10, Excellent, (1004)
"A great place "
The price is NZ$278
includes taxes & fees
9 July - 10 July
Ivy Boutique Hotel
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Lobby

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3.0 star property
8.4 out of 10, Very good, (1883)
"Great stay! "
The price is NZ$277
includes taxes & fees
7 Aug - 8 Aug
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Hyatt Regency Chicago
Room, 2 Queen Beds, Lake View

Hyatt Regency Chicago

4.0 star property
9.2 out of 10, Wonderful, (3267)
"Great location and stay"
The price is NZ$515
includes taxes & fees
6 Aug - 7 Aug
Hyatt Regency Chicago
Hilton Chicago/Magnificent Mile Suites
Exterior

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2403)
"Friendly staff, beautiful views, excellent location "
The price is NZ$328
includes taxes & fees
10 July - 11 July
Hilton Chicago/Magnificent Mile Suites
Millennium Knickerbocker Chicago
View from property

Millennium Knickerbocker Chicago

4.0 star property
8.6 out of 10, Excellent, (1877)
"Great location near bars and restaurants "
The price is NZ$296
includes taxes & fees
8 July - 9 July
Millennium Knickerbocker Chicago
Hyatt Centric Chicago Magnificent Mile
Room, 1 King Bed, Corner

Hyatt Centric Chicago Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (1025)
"Nice hotel "
The price is NZ$434
includes taxes & fees
10 July - 11 July
Hyatt Centric Chicago Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile
Breakfast and dinner served

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.2 out of 10, Good, (1102)
"We enjoyed our time at this stay. "
The price is NZ$249
includes taxes & fees
8 July - 9 July
The Chicago Hotel Collection - Magnificent Mile
Hotel Saint Clair- Magnificent Mile
Restaurant

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (1643)
"Great stay"
Hotel Saint Clair- Magnificent Mile
Best Western Grant Park Hotel
Restaurant

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very good, (2554)
"Great stay"
The price is NZ$278
includes taxes & fees
10 July - 11 July
Best Western Grant Park Hotel
Congress Plaza Hotel
Aerial view

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (8910)
"Great location, beautiful hotel "
The price is NZ$277
includes taxes & fees
4 Aug - 5 Aug
Congress Plaza Hotel
Le Méridien Essex Chicago
City view

Le Méridien Essex Chicago

4.0 star property
8.6 out of 10, Excellent, (1004)
"Location is great and property was very clean "
The price is NZ$367
includes taxes & fees
4 Aug - 5 Aug
Le Méridien Essex Chicago
InterContinental Chicago Magnificent Mile by IHG
Exterior

InterContinental Chicago Magnificent Mile by IHG

4.5 star property
9.0 out of 10, Wonderful, (1994)
"Nice hotel and the staff was great."
The price is NZ$554
includes taxes & fees
7 Aug - 8 Aug
InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago
Exterior

Hilton Chicago

4.0 star property
8.4 out of 10, Very good, (1986)
"Great stay! "
The price is NZ$405
includes taxes & fees
4 Aug - 5 Aug
Hilton Chicago
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.

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 map

Downtown Chicago

5 out of top 10 points of interest in this area

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 - River North
Magnificent Mile map

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 - Downtown which includes a river or creek
The Loop map

The Loop

Michigan Avenue and Art Institute of Chicago 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 map

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 map

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.

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.