Sleepy Hollow, IL
Chicago
Visit Sleepy Hollow
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Sleepy Hollow Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
$136 nightly
The price is $162 total per night from Jun 29 to Jun 30
$162 total
Jun 29 - Jun 30
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (10,139 reviews)
"4 days of a cold shower and a broken bed. I will never stay here again and I suggest that anyone thinking about staying here to look elsewhere. Bathrooms were severely outdated."
Reviewed on Jun 27, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
$181 nightly
The price is $215 total per night from Jul 5 to Jul 6
$215 total
Jul 5 - Jul 6
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,828 reviews)
"Best location on Michigan Avenue"
Reviewed on Jun 27, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
$147 nightly
The price is $175 total per night from Jul 6 to Jul 7
$175 total
Jul 6 - Jul 7
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
9/10 Wonderful! (4,467 reviews)
"The housekeeper was always so friendly and did such a great job. Honestly, all the staff was fantastic and so helpful."
Reviewed on Jun 27, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
$127 nightly
The price is $145 total per night from Jun 29 to Jun 30
$145 total
Jun 29 - Jun 30
Total with taxes and fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,735 reviews)
"This place was very busy but they managed to keep it clean. Friendly and helpful staff."
Reviewed on Jun 27, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
$245 nightly
The price is $288 total per night from Jul 18 to Jul 19
$288 total
Jul 18 - Jul 19
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (2,320 reviews)
"Staffs were ridiculous. Never thought I would hear that “he works for tips not free”. I paid $500 including tax and this is what I was told. And daughter got bit by I don’t know what all over her body. I don’t know how all of the treatments they think was okay to a customer. We didn’t ask for much ..."
Reviewed on Jun 27, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
$194 nightly
The price is $231 total per night from Jul 5 to Jul 6
$231 total
Jul 5 - Jul 6
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (4,559 reviews)
"Lovely property all the way around!"
Reviewed on Jun 27, 2026
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.
Where to stay in Sleepy Hollow
Find the best Sleepy Hollow areas and neighborhoods for the activities you enjoy most. Learn more about Sleepy Hollow
Learn more about Sleepy Hollow
Downtown Chicago
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
Michigan Avenue and Chicago Water Tower are just a few worthwhile attractions to visit in Magnificent Mile. Travelers also love the fascinating museums, panoramic lake views, and popular shops.
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.
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 Oz Park, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.
Sleepy Hollow, IL
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- Visit Hyde Park
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- Where to stay in Chicago
- Visit South Loop
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- Visit Garfield Manor
- Visit Chicago
