Sleepy Hollow Hotels, Chicago

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13 July - 14 July
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14 July - 15 July
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18 July - 20 July
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25 July - 27 July

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4666 Cheap Hotels in Sleepy Hollow - Specials, Reviews, & Last Minute Deals

Holiday Inn Chicago O'Hare – Rosemont by IHG
Relax on a long, cushioned bench amidst scenic views of the water.

Holiday Inn Chicago O'Hare – Rosemont by IHG

3.0 star property
8.8 out of 10, Excellent, (2171)
"Great stay near the airport for an early flight. "
The price is AU$181
includes taxes & fees
10 Aug - 11 Aug
Holiday Inn Chicago O'Hare – Rosemont by IHG
Arlo Chicago
Welcome to the Arlo hotel, featuring a modern entrance with a glass facade and brick and stone architecture.

Arlo Chicago

4.0 star property
9.2 out of 10, Wonderful, (1796)
"Great stay"
The price is AU$373
includes taxes & fees
10 Aug - 11 Aug
Arlo Chicago
Fairmont Chicago at Millennium Park
Enjoy a meal in the kitchen with a large island and dining area, offering a view of the city skyline.

Fairmont Chicago at Millennium Park

4.5 star property
8.6 out of 10, Excellent, (1804)
"Great stay, great location and very polite staff "
The price is AU$453
includes taxes & fees
8 Aug - 9 Aug
Fairmont Chicago at Millennium Park
Warwick Allerton - Chicago
Formal dining area with a large chandelier, gold chairs, and a stone floor.

Warwick Allerton - Chicago

4.0 star property
8.2 out of 10, Very good, (2869)
"Just a great place to stay"
The price is AU$239
includes taxes & fees
11 Aug - 12 Aug
Warwick Allerton - Chicago
La Quinta by Wyndham Chicago O'Hare Airport
Relax in a stylish space with a seating area, dining table, and flat-screen TV.

La Quinta by Wyndham Chicago O'Hare Airport

3.0 star property
8.4 out of 10, Very good, (1657)
"Very new hotel with a Great breakfast"
The price is AU$168
includes taxes & fees
12 Aug - 13 Aug
La Quinta by Wyndham Chicago O'Hare Airport
Millennium Knickerbocker Chicago
Experience the grandeur of our lobby, featuring a stunning chandelier, comfortable seating, and a beautiful staircase.

Millennium Knickerbocker Chicago

4.0 star property
8.6 out of 10, Excellent, (1881)
"Great location near bars and restaurants "
The price is AU$262
includes taxes & fees
13 Aug - 14 Aug
Millennium Knickerbocker Chicago
Thompson Chicago, by Hyatt
Stairs lead to a bar area with a counter and seating on the upper level.

Thompson Chicago, by Hyatt

4.5 star property
9.0 out of 10, Wonderful, (1163)
"Great location and property!"
The price is AU$300
includes taxes & fees
10 Aug - 11 Aug
Thompson Chicago, by Hyatt
Wyndham Chicago O'Hare
Welcome to Wyndham, where a prominent stone pillar marks the entrance, complemented by a metal canopy.

Wyndham Chicago O'Hare

3.0 star property
8.4 out of 10, Very good, (1011)
"Everything was great. There was a few ants, but overall good. I would stay here again."
The price is AU$193
includes taxes & fees
20 July - 21 July
Wyndham Chicago O'Hare
Hotel Chicago Downtown, Autograph Collection by Marriott
Relax in a spacious lobby with a large seating area, sofas, armchairs, and tables for guests.

Hotel Chicago Downtown, Autograph Collection by Marriott

4.0 star property
9.0 out of 10, Wonderful, (1007)
"Amazing stay ! "
The price is AU$400
includes taxes & fees
27 July - 28 July
Hotel Chicago Downtown, Autograph Collection by Marriott
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Experience the hotel's inviting atmosphere, featuring a spacious lobby with large windows, comfortable seating, and a cozy reading nook.

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3.0 star property
8.4 out of 10, Very good, (1897)
"Great stay! "
The price is AU$244
includes taxes & fees
10 Aug - 11 Aug
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Ohio House Motel
Located at the corner of a bustling street, Ohio House features a flat roof and large glass windows.

Ohio House Motel

2.5 star property
9.0 out of 10, Wonderful, (1018)
"Great place to stay!"
The price is AU$228
includes taxes & fees
10 Aug - 11 Aug
Ohio House Motel
Hyatt House Chicago West Loop
Enjoy panoramic city views from this rooftop terrace, featuring a spacious seating area and dining space with a glass balustrade.

Hyatt House Chicago West Loop

3.5 star property
8.8 out of 10, Excellent, (1020)
"Great hotel for families! "
The price is AU$352
includes taxes & fees
10 Aug - 11 Aug
Hyatt House Chicago West Loop
Holiday Inn & Suites Chicago - Downtown by IHG
Relax by the rooftop pool with a stunning view of the city skyline.

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
8.4 out of 10, Very good, (1011)
"Nice place to stay"
The price is AU$288
includes taxes & fees
10 Aug - 11 Aug
Holiday Inn & Suites Chicago - Downtown by IHG
LondonHouse Chicago, Curio Collection by Hilton
Contemporary lounge area with a striking metal structure and large windows offering urban views.

LondonHouse Chicago, Curio Collection by Hilton

4.5 star property
9.4 out of 10, Exceptional, (3339)
"Great stay"
The price is AU$311
includes taxes & fees
10 Aug - 11 Aug
LondonHouse Chicago, Curio Collection by Hilton
L7 Chicago by LOTTE
Stunning hotel exterior with a sleek glass canopy and modern design.

L7 Chicago by LOTTE

4.5 star property
9.6 out of 10, Exceptional, (2642)
"Very nice location and great restaurant on the premises "
The price is AU$396
includes taxes & fees
27 July - 28 July
L7 Chicago by LOTTE
Aloft Chicago Mag Mile
Conference room with a large, round table and six chairs, offering city views.

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2758)
"Great location and friendly staff"
The price is AU$319
includes taxes & fees
6 Aug - 7 Aug
Aloft Chicago Mag Mile
Hotel Felix River North/Magnificent Mile
Relax in the hotel lobby, featuring a spacious seating area with a sofa, armchairs, and a small table.

Hotel Felix River North/Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (1861)
"Great location "
The price is AU$498
includes taxes & fees
23 July - 24 July
Hotel Felix River North/Magnificent Mile
Sonesta Simply Suites Chicago O'Hare Airport
Enjoy cooking in this well-equipped kitchen with a stainless steel refrigerator, microwave, and coffee maker.

Sonesta Simply Suites Chicago O'Hare Airport

2.0 star property
8.4 out of 10, Very good, (1823)
"Very comfortable stay. "
The price is AU$176
includes taxes & fees
20 July - 21 July
Sonesta Simply Suites Chicago O'Hare Airport
The Godfrey Hotel Chicago
Enjoy a drink at the bar, where a geometric ceiling structure and contemporary design create a welcoming atmosphere.

The Godfrey Hotel Chicago

4.5 star property
8.6 out of 10, Excellent, (1890)
"Great hotel in a great location. Would definitely stay again "
The price is AU$337
includes taxes & fees
27 July - 28 July
The Godfrey Hotel Chicago
Viceroy Chicago
Classic entrance with a curved doorway and decorative glass window, set amidst intricate brickwork and ornate details.

Viceroy Chicago

4.5 star property
9.4 out of 10, Exceptional, (1049)
"Great location and big, spacious room. "
The price is AU$589
includes taxes & fees
10 Aug - 11 Aug
Viceroy 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.