Sleepy Hollow Holidays from £716

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Your Sleepy Hollow Holiday

Entertainment, history, art and more … There's so much to experience with a Sleepy Hollow holiday package. And with the ability to customise your city getaway, it's guaranteed to be one you won't forget. Make your trip to Sleepy Hollow even more fun by going sightseeing. Grand Victoria Casino, Santas Village and NOW Arena are among the top attractions worth exploring. Whatever your travel plans or budget, organising your ultimate tailored Sleepy Hollow holiday is simple with Expedia.

Top Sleepy Hollow Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was £1,146, price is now £716 per person
£716
per person
16 Oct - 21 Oct
just found
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Great location and room was fantastic! Only negatives were a lengthy check in and access to the outside deck was closed at 10 PM. Probably a good idea for that, but it would’ve been nice to go out there for a nightcap.

Reviewed on 26 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,928, price is now £1,178 per person
£1,178
per person
16 Oct - 21 Oct
just found
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on 25 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,113, price is now £1,322 per person
£1,322
per person
10 Nov - 16 Nov
found 24 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,244, price is now £783 per person
£783
per person
16 Oct - 21 Oct
just found
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,087 reviews)
Perfect location! Friendly staff. Beautiful room overlooking skyline and water.

Reviewed on 26 Aug 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,374, price is now £867 per person
£867
per person
16 Oct - 21 Oct
just found
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (339 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on 27 Aug 2025

Sleepy Hollow Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
3,300
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Santas Village, Hemmens Cultural Centre and Epic Air Trampoline Park

Top hotels in Sleepy Hollow

Wyndham Garden Schaumburg Chicago Northwest

Wyndham Garden Schaumburg Chicago Northwest

3 out of 5
1725 E Algonquin Road, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is £58 per night from 11 Sept to 12 Sept
£58
11 Sept - 12 Sept
includes taxes & fees
6.6/10 (1,009 reviews)
"The room could have been cleaner, especially the bathtub/shower"

Reviewed on 23 Aug 2025

Wyndham Garden Schaumburg Chicago Northwest
DoubleTree by Hilton Libertyville - Mundelein

DoubleTree by Hilton Libertyville - Mundelein

4 out of 5
510 E IL Route 83, Mundelein, IL
Fully refundableReserve now, pay when you stay
The price is £90 per night from 21 Sept to 22 Sept
£90
21 Sept - 22 Sept
includes taxes & fees
DoubleTree by Hilton Libertyville - Mundelein
Motel 6 Elk Grove Village, IL

Motel 6 Elk Grove Village, IL

2 out of 5
1000 W Devon Ave, Elk Grove Village, IL
Fully refundableReserve now, pay when you stay
The price is £40 per night from 16 Sept to 17 Sept
£40
16 Sept - 17 Sept
includes taxes & fees
7.8/10 Good! (1,012 reviews)
"Good"

Reviewed on 26 Aug 2025

Motel 6 Elk Grove Village, IL
See all 482 properties in Sleepy Hollow
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

Why should I book my Sleepy Hollow holiday with Expedia?
Expedia has your back for every aspect of your Sleepy Hollow getaway. You'll always get the best deals around, but when you bundle your hotel, flights and/or car hire into a holiday package, you'll score even bigger savings. Keen to really make the most of your escape? Add some fun activities and tours to your package. Expedia offers flexible cancellation policies on almost all bookings, so you won't need to worry if you have to change your plans. Head over to our Customer Service Portal link to learn more.
When is the best time of year to holiday in Sleepy Hollow?
If you enjoy the buzz of peak season, head to Sleepy Hollow in May, June and August. If you'd like a more relaxed vibe, December, January and February are better times to visit. With average daytime temperatures of -5ºC, January is the coolest month in Sleepy Hollow. The warmest time of year is July, when you can expect average temperatures of 22ºC throughout the day. Whatever the temperature, you'll find plenty to keep you occupied here.
What is the top hotel for my holiday in Sleepy Hollow?
LondonHouse Chicago, Curio Collection by Hilton is the ideal base for an unforgettable trip to Sleepy Hollow, offering all the comforts and conveniences you need and more.
How do I get a cheap holiday to Sleepy Hollow?
Creating your own Sleepy Hollow holiday with Expedia is a simple way to save. We offer more than 400 partner airlines and 321,000 hotels globally. With such a fantastic range to select from, you'll have no trouble putting together your dream adventure. Learn more about how you can save money on your holiday when you combine your flight and hotel bookings with Expedia.
What should I do on my Sleepy Hollow holiday?
There's an almost endless list of things to keep you busy during your holiday in Sleepy Hollow. Grand Victoria Casino, Santas Village, NOW Arena and Elgin Sports Complex are some of this city's most popular attractions.
Do I need a visa for my Sleepy Hollow holiday?
Official government websites will have all the information you need on visa requirements, application procedures and any supporting documentation. Your nationality and the reason for your visit, whether it be for holidays or business, will determine if you need a visa for Sleepy Hollow. Be sure that your passport is up to date and has a minimum of six months validity remaining beyond your intended return date. Do all your travel planning well ahead of time to avoid any nasty last-minute surprises.
What should I wear on my Sleepy Hollow holiday?
Although everyone's fashion style is different, it can be helpful to have some guidelines for what to wear during your holiday in Sleepy Hollow. Think about searching style blogs before leaving for inspiration on local fashion trends. Daytime temperatures in January, Sleepy Hollow's coolest month, average -5ºC. July marks this city's warmest month when the average reaches 22ºC. Our top piece of advice? Take the guesswork out of packing and check the local weather forecast.
What does an Expedia Sleepy Hollow holiday include?
Hotels, flights and car hires, or any combination of the three — it's your choice. Whether you're headed to Sleepy Hollow with the family or travelling with your friends, there's a bundle to fit every budget and style. Once you've made your booking, why not add on a few tours and experiences? Expedia features all types of properties, with the most sought after in Sleepy Hollow being apartments and private holiday homes. With Expedia, you'll always have the flexibility and freedom to design your holiday any way you like.
Does Expedia offer Book Now, Pay Later Sleepy Hollow holidays?
Your bank balance shouldn't get in the way of going on holiday, so Expedia has devised a solution to help. Now that we've formed a partnership with online lender Klarna, it's easier than ever to book your dream getaway without using up all your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your escape. Check out these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month sounds right for you, Klarna can help. Paying in several transactions will make that dream holiday possible.
  • No-deposit holidays: If no upfront fee for your getaway makes hitting that "book now" button easier, opt for a no-deposit holiday plan from Klarna so you can Book Now, Pay Later!

Can I choose my airline with a Sleepy Hollow Expedia holiday?
Yes, definitely. Expedia has over 400 airline partners to pick from across the world. With all that choice, finding the right carrier to take you to Sleepy Hollow will be a snap.

* 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.