Sleepy Hollow, IL
Chicago
Visit Sleepy Hollow
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
$158
per adult
80% of travellers recommend
LEGOLAND® Discovery Center Chicago
$26
per adult
92% of travellers recommend
Museum of Illusions Chicago Admission Ticket
$43
per adult
Sleepy Hollow Hotel Deals
River Hotel
75 East Wacker Drive Chicago IL
$186 nightly
The price is $221 total per night from Oct 25 to Oct 26
$221 total
Oct 25 - Oct 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (5,447 reviews)
"The staff at this hotel were all very friendly and helpful. I requested extra coffee and other supplies for the room several times and they never failed to bring it to our room promptly. I did think the interior of our room was a bit outdated and could use some updating. The furniture, carpet, and ..."
Reviewed on Sep 30, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
$152 nightly
The price is $180 total per night from Oct 25 to Oct 26
$180 total
Oct 25 - Oct 26
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 ...
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
$179 nightly
The price is $213 total per night from Oct 25 to Oct 26
$213 total
Oct 25 - Oct 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (2,381 reviews)
"For the location & prestige, the grandeur was all in the external. The room was shabby, the carpet worn & marked (with bleach?) in several places, the amenities were severely lacking (front desk did not even have a sewing kit), staff were running on empty and ragged. Perhaps I had a lot of expectations ..."
Reviewed on Sep 30, 2026
Hampton Inn Chicago Downtown/Magnificent Mile
160 E Huron Street Chicago IL
$203 nightly
The price is $242 total per night from Oct 25 to Oct 26
$242 total
Oct 25 - Oct 26
Total with taxes and fees
Book a stay at this family-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the ...
8/10 Very Good! (1,640 reviews)
"Traveling cross country and stayed at several hotel. This one was on point, from entering the hotel, smelling clean, the staff checking in was great, and the room was clean. I had an awesome stay."
Reviewed on Sep 29, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
$179 nightly
The price is $213 total per night from Oct 25 to Oct 26
$213 total
Oct 25 - Oct 26
Total with taxes and fees
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
8/10 Very Good! (2,277 reviews)
"Clean room"
Reviewed on Sep 30, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$190 nightly
The price is $226 total per night from Oct 30 to Oct 31
$226 total
Oct 30 - Oct 31
Total with taxes and fees
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (3,319 reviews)
"Staff was friendly and the hotel was clean. Our room was by the CTA so we heard that running all night."
Reviewed on Sep 30, 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 Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
Photo by © City of Chicago
Open Photo by © City of Chicago
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 Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.
Sleepy Hollow, IL
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