Sleepy Hollow Hotels, Chicago

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Check prices for these dates

Tonight
30 Aug - 31 Aug
Tomorrow
31 Aug - 1 Sept
Next weekend
5 Sept - 7 Sept
In two weeks
12 Sept - 14 Sept

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4907 Cheap Hotels in Sleepy Hollow - Specials, Reviews, & Last Minute Deals

FOUND Hotel Chicago River North
Exterior

FOUND Hotel Chicago River North

2.0 star property
8.2 out of 10, Very good, (214)
"Great place "
The price is AU$176
includes taxes & fees
2 Sept - 3 Sept
FOUND Hotel Chicago River North
Ohio House Motel
Reception

Ohio House Motel

3.0 star property
9.0 out of 10, Wonderful, (1010)
"Awesome place to stay. "
The price is AU$197
includes taxes & fees
2 Sept - 3 Sept
Ohio House Motel
Level Chicago Fulton Market
Executive lounge

Level Chicago Fulton Market

4.0 star property
9.2 out of 10, Wonderful, (275)
"The staff was excellent the amenities were a fantastic overall a great experience "
The price is AU$400
includes taxes & fees
1 Sept - 2 Sept
Level Chicago Fulton Market
Holiday Inn Express Chicago - Magnificent Mile by IHG
Exterior

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 star property
8.4 out of 10, Very good, (1022)
"Great hotel! "
The price is AU$273
includes taxes & fees
4 Sept - 5 Sept
Holiday Inn Express Chicago - Magnificent Mile by IHG
Travelodge by Wyndham Downtown Chicago
Lobby

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.2 out of 10, Good, (2330)
"I had a very good stay 10 out of 10 recommend"
The price is AU$176
includes taxes & fees
2 Sept - 3 Sept
Travelodge by Wyndham Downtown Chicago
Best Western Grant Park Hotel
Restaurant

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very good, (2624)
"Great hotel! "
The price is AU$197
includes taxes & fees
3 Sept - 4 Sept
Best Western Grant Park Hotel
Pendry Chicago
View from property

Pendry Chicago

4.5 star property
9.4 out of 10, Exceptional, (1067)
"Wonderful Stay."
The price is AU$485
includes taxes & fees
21 Sept - 22 Sept
Pendry Chicago
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (9082)
"Family had a great stay. "
The price is AU$354
includes taxes & fees
15 Sept - 16 Sept
Congress Plaza Hotel
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (3673)
"Great place to stay "
The price is AU$258
includes taxes & fees
2 Sept - 3 Sept
citizenM Chicago Downtown
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very good, (2258)
"Great stay "
The price is AU$184
includes taxes & fees
3 Sept - 4 Sept
Freehand Chicago
The Chicago Hotel Collection River North
Building design

The Chicago Hotel Collection River North

3.0 star property
7.2 out of 10, Good, (578)
"It was a wonderful place to stay! "
The price is AU$229
includes taxes & fees
1 Sept - 2 Sept
The Chicago Hotel Collection River North
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, (1031)
"Great stay"
The price is AU$357
includes taxes & fees
1 Sept - 2 Sept
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Hilton Chicago
Exterior

Hilton Chicago

4.0 star property
8.4 out of 10, Very good, (2144)
"Amazing stay and great location…"
The price is AU$375
includes taxes & fees
14 Sept - 15 Sept
Hilton Chicago
Residence Inn Chicago Downtown Magnificent Mile
Aerial view

Residence Inn Chicago Downtown Magnificent Mile

4.0 star property
9.6 out of 10, Exceptional, (334)
"Enjoyable stay at this Hotel in a very large room close to all the sights and shopping."
The price is AU$375
includes taxes & fees
1 Sept - 2 Sept
Residence Inn Chicago Downtown Magnificent Mile
Central Loop Hotel
Breakfast, lunch, dinner served; American cuisine

Central Loop Hotel

4.0 star property
8.6 out of 10, Excellent, (1835)
"Amazing place to stay"
The price is AU$232
includes taxes & fees
1 Sept - 2 Sept
Central Loop Hotel
Palmer House a Hilton Hotel
Ballroom

Palmer House a Hilton Hotel

4.0 star property
8.4 out of 10, Very good, (1911)
"Helpful staff, beautiful hotel in a great location!"
The price is AU$415
includes taxes & fees
25 Sept - 26 Sept
Palmer House a Hilton Hotel
Kimpton Gray Hotel by IHG
Argentinean cuisine

Kimpton Gray Hotel by IHG

4.5 star property
9.2 out of 10, Wonderful, (1009)
"Great stay!"
The price is AU$425
includes taxes & fees
5 Sept - 6 Sept
Kimpton Gray Hotel by IHG
Club Quarters Hotel, Central Loop, Chicago
Breakfast, lunch and dinner served

Club Quarters Hotel, Central Loop, Chicago

4.0 star property
8.6 out of 10, Excellent, (3371)
"Great location, quiet rooms "
The price is AU$232
includes taxes & fees
1 Sept - 2 Sept
Club Quarters Hotel, Central Loop, Chicago
Hotel Saint Clair- Magnificent Mile
Restaurant

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (1704)
"Had a great stay! The area is very walkable and convenient!!"
Hotel Saint Clair- Magnificent Mile
Chicago Athletic Association, a Hyatt Hotel
Exterior

Chicago Athletic Association, a Hyatt Hotel

4.5 star property
9.0 out of 10, Wonderful, (1002)
"Fantastic place to stay….close to the lake, shopping and dining."
The price is AU$341
includes taxes & fees
1 Sept - 2 Sept
Chicago Athletic Association, a Hyatt Hotel
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

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

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

Michigan Avenue and Lake Michigan 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

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

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.

Top Sleepy Hollow Hotel Reviews

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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?

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.