Sleepy Hollow Holidays from £1,013
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- Better togetherSave up to £750 when you book a flight and hotel together*
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- Rest easyPackages with flights are ATOL protected
Your Sleepy Hollow Holiday
Make travel planning hassle-free by snapping up a holiday package to Sleepy Hollow. Let us handle the minutiae, so you can focus on savouring everything this neighbourhood has to offer. Your trip to Sleepy Hollow wouldn't be complete without exploring leading attractions nearby such as Morton College, Hawthorne Works Museum and Balzekas Museum of Lithuanian Culture. Whatever your travel plans or the size of your budget, booking your ideal Sleepy Hollow holiday is simple with Expedia.
Where to stay in Sleepy Hollow
Downtown Chicago
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
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
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Top hotels in Sleepy Hollow
Congress Plaza Hotel
River Hotel
The Chicago Hotel Collection - Magnificent Mile
"It was so clean and comfortable. The staff was so friendly. The location is perfect! I would stay here again."
Reviewed on 14 Oct 2026
Frequently asked questions
How much does a Sleepy Hollow travel package cost?
If I'm not able to travel, can I cancel my Sleepy Hollow travel package?
How do I get a cheap travel package to Sleepy Hollow?
Does Expedia offer Book Now, Pay Later Sleepy Hollow holidays?
- Pay monthly holidays: If paying bite-sized amounts each month sounds right for you, Klarna offers just that! Paying in convenient monthly instalments will make your getaway dreams come true.
- Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay off your holiday across multiple transactions.
- Low deposit holidays: When you stumble on an incredible deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you lock in your escape.
Where should I stay in Sleepy Hollow?
What are the top hotels in Sleepy Hollow?
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Can I choose my airline with a Sleepy Hollow Expedia travel package?
Things to do
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.