Sleepy Hollow Vacations from $597
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Your Sleepy Hollow Vacation
Experience everything this neighborhood has to offer with a tailor-made Sleepy Hollow vacation package. However you picture yourself spending your time here, you'll find endless opportunities for fun, relaxation and adventure. What to cross off your itinerary first? Nearby Balzekas Museum of Lithuanian Culture is one thing you can't miss during your trip to Sleepy Hollow. Expedia will help turn your dream Sleepy Hollow vacation into reality, whatever your travel plans or budget.
The Latest Sleepy Hollow Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
Price was $910, price is now $597 per person
$597
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
The rooms were spotless and very well tended to. My wife and I really enjoyed how central it was to many stores, restaurants, and places of interest. We also enjoyed the bar, with its selection of great drinks; it was a great way to relax after walking around Chicago all day!
Reviewed on Jul 4, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,078, price is now $662 per person
$662
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
The room was very small for 4 people. It has pull-out coach for 2 people and in reality one person sleeps comfortably. It is not for two people.
Reviewed on Jul 4, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,476, price is now $1,595 per person
$1,595
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Excellent hotel. We love staying there whenever we visit Chicago.
Reviewed on Jul 3, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,192, price is now $773 per person
$773
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026
Wind Creek Southland Casino and Hotel
East Hazel Crest
Save 100% on your flight
Price was $1,015, price is now $660 per person
$660
per person
Aug 7 - Aug 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (450 reviews)
Staff was very helpful and room was clean 👌
Reviewed on Jul 4, 2026
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
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Sleepy Hollow Hotel Deals
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $171 total per night from Jul 5 to Jul 6
$171 total
Jul 5 - Jul 6
Total with taxes and fees
8.2/10 Very Good! (1,684 reviews)
"Absolutely wonderful experience staying here beautiful view of the city. Complimentary breakfast was wonderful and extremely friendly and helpful staff. Highly recommend staying here"
Reviewed on Jul 3, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $144 total per night from Jul 6 to Jul 7
$144 total
Jul 6 - Jul 7
Total with taxes and fees
8/10 Very Good! (10,148 reviews)
"We got in pretty late. The front desk staff that assisted us barely put more than 5 words together. He didn’t give any information..most of all the things that didn’t work/broken. The room was extremely small, the bathroom so tight if you closed the door while on the toilet your knees would be jammed ..."
Reviewed on Jul 3, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
$174 nightly
The price is $207 total per night from Jul 8 to Jul 9
$207 total
Jul 8 - Jul 9
Total with taxes and fees
9.2/10 Wonderful! (1,843 reviews)
"The rooms were spotless and very well tended to. My wife and I really enjoyed how central it was to many stores, restaurants, and places of interest. We also enjoyed the bar, with its selection of great drinks; it was a great way to relax after walking around Chicago all day!"
Reviewed on Jul 4, 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.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.