Sleepy Hollow Holidays from £1,401
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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.
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
£1,661
per person
7 Oct - 12 Oct
found 5 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Room was ok, didn’t get the view I requested.
Some of the reception people was rude. Breakfast was adequate. No omellete bar,
Reviewed on 29 Aug 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
£1,540
per person
7 Oct - 12 Oct
found 5 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,654 reviews)
The hotel was clean. The staff was amazing. The location is also great. I love being right on the water. Perfect for a stroll outside on the boardwalk.
Reviewed on 29 Aug 2026
Silversmith Hotel Chicago Downtown
Downtown Chicago
£1,797
per person
7 Oct - 12 Oct
found 5 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (2,373 reviews)
We really like Silversmith. We've been there a couple of times. A smaller historical hotel and a bit more personal. We like the Loop! Staff was very good. Susan worked it all out for our group of 4 rooms. Good rooms. Try the "pure wellness" rooms. Quite nice. The attached Adamus restaurant, bar and lounge, was great; breakfast and dinner. The restaurant and bar staff were very attentive and personable! Renee was a fab bertender. Millennium Park and museums are a couple short blocks away. Very good home base to get something done or just explore Chicago.
Reviewed on 29 Aug 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
4 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.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
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
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£94
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,203 reviews)
"The hotel is old and needs a renovation. Carpets are worn and dirty, and you can tell that it hasn't had a refresh in 30+ years. However, we left important medicine behind and we coordinated with them to have it sent to us at our next stop...they were VERY helpful in this regard so despite a negative ..."
Reviewed on 29 Aug 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
£126
31 Aug - 1 Sept
includes taxes & fees
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
£202
18 Sept - 19 Sept
includes taxes & fees
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.
Frequently asked questions
How much does a Sleepy Hollow travel package cost?
Get your credit card ready, because a trip to Sleepy Hollow starts from an enticing £1,401. When you combine your flights, hotels and more into a travel package, you'll land the best prices.
If I'm not able to travel, can I cancel my Sleepy Hollow travel package?
Because we know life is full of surprises, the answer is yes. For more information, check out our Customer Service Portal. But generally speaking, if you've made your booking in the last 24 hours, you may be able to change or cancel it for free. Your hotel, airline or car rental company may charge a fee if you made your booking a while ago.
How do I get a cheap travel package to Sleepy Hollow?
Booking a Sleepy Hollow travel package with Expedia is a simple way to save. We offer more than 550 partner airlines and 1,000,000 hotels worldwide. With such a wonderful range to pick from, you'll have no difficulty creating your ideal holiday.
Does Expedia offer Book Now, Pay Later Sleepy Hollow holidays?
Expedia has teamed up with online lender Klarna to make booking your next break easier on your hip pocket. Paying in instalments means you can spread the costs of your dream holiday, leaving you with more cash to spend while you're travelling. Klarna has several payment plans to choose from, so you're sure to find one that fits your budget. Browse these flexible payment options:
- 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?
Make sightseeing easy by staying near Sleepy Hollow's biggest attractions. Millennium Park and Wrigley Field are two traveller favourites.
What are the top hotels in Sleepy Hollow?
Get your escape off to a good start by reserving a room at Hyatt Regency Chicago. It's one of most popular properties in Sleepy Hollow. Another comfortable option is The Godfrey Hotel Chicago.
How far in advance should I book my Sleepy Hollow holiday?
To land rock-bottom prices, book ASAP. Airlines usually start selling tickets, along with some of the lowest fares, around a year prior to departure. Hotels, car rental and experiences should also be booked early so you can have the pick of the bunch. If you're in need of a last-minute getaway to Sleepy Hollow, there are always lots of great deals on Expedia. Book your escape today!
What does an Expedia Sleepy Hollow travel package include?
Flights, hotels and rental cars — we've got them covered. With Expedia, you can create your Sleepy Hollow package just the way you want. All you have to do is decide just what you need. Once you've made your booking, you can add on extras like experiences and activities. The more you bundle, the greater the savings!
What should I know before booking a Sleepy Hollow travel package?
Our prices are already low. However, you'll snap up even more savings when you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and lots of choice.
Can I choose my airline with a Sleepy Hollow Expedia travel package?
Most definitely. Expedia has access to more than 550 partner airlines across the globe, so you can customize your Sleepy Hollow escape according to your style and budget.
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
£35
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
£30
per adult
94% of travellers recommend
* 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.