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.

Sleepy Hollow Holiday Packages, Fully Refundable Options on Hotels

Name: DoubleTree by Hilton Libertyville - Mundelein
Price range: £101
Rating: 8.6

Top Sleepy Hollow Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.

Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

£1,262

per person

28 Sept - 5 Oct

just found

Return direct flight included

Manchester (MAN) to Chicago (ORD)

8.8/10 Excellent! (2,393 reviews)

Level Chicago – Old Town

Downtown Chicago

£1,412

per person

17 Sept - 21 Sept

found 1 day ago

Return flight included

London (LON) to Chicago (ORD)

9/10 Wonderful! (504 reviews)

this is no a hotel and the amenities are bare bones. No maid service, the TV was worthless with endless buffering to make it unwatchable, the shower head was broken, etc. On the good side, it's a great location, beautiful views, nice vibe around the property, large unit with two beds, and great gym area.

Reviewed on 27 Jul 2026

Four Seasons Hotel Chicago

Downtown Chicago

£2,375

per person

14 Sept - 18 Sept

found 1 day ago

Return flight included

London (LON) to Chicago (ORD)

9.4/10 Exceptional! (1,002 reviews)

The Hoxton, Chicago

Downtown Chicago

£1,354

per person

15 Oct - 20 Oct

found 2 hours ago

Return direct flight included

London (LON) to Chicago (ORD)

9.2/10 Wonderful! (1,005 reviews)

Great location for what I needed

Reviewed on 28 Jul 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

£1,794

per person

27 Aug - 31 Aug

found 1 day ago

Return flight included

London (LON) to Chicago (ORD)

9.6/10 Exceptional! (1,945 reviews)

Wasn’t as catered to as most hotels at this price point. Best thing was size of room

Reviewed on 27 Jul 2026

Things to do near Sleepy Hollow

Sleepy Hollow is perfect for family-friendly, outdoor, and city-themed holidays. Visitors can enjoy a variety of activities, including exploring shopping centres, educational attractions, and seasonal events. Key highlights include Halloween night festivities, live music performances, exciting new attractions, and fun tours that cater to all ages, ensuring a memorable experience for everyone.

Shopping

For a delightful shopping experience in Sleepy Hollow, visit Cabela's, only 8.0km away, for outdoor gear. The Crystal Court Shopping Center offers entertainment and family vibes, located 14.5km from town. If you're up for a drive, the Arboretum of South Barrington is 9.7km away, featuring diverse shopping options.

Recreation

Enjoy a cinematic experience at The Catlow Theater, where you can catch a film in a charming setting perfect for families and romance. For outdoor enthusiasts, the Randall Oaks Golf Club offers a delightful golfing experience amidst beautiful landscapes. Don't miss the Hemmens Cultural Center for a taste of local culture and entertainment.

Adventure

Explore the Algonquin Lakes Trailhead, a scenic trail located 6.4km from Sleepy Hollow, perfect for outdoor enthusiasts. For a picturesque hike, visit the Spring Lake Valley Forest Preserve Trailhead, situated 8.0km away, offering breathtaking views. For family fun, enjoy the Epic Air Trampoline Park, located 12.9km from Sleepy Hollow.

Nightlife

In Sleepy Hollow, enjoy a relaxed evening at The Village Squire, known for its hearty meals and lively atmosphere. For a more laid-back vibe, unwind at the local pub, The Sleepy Hollow Tavern, where you can savour a pint and engage in friendly conversation with locals.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Sleepy Hollow

Sleepy Hollow, Illinois, offers a delightful blend of family-friendly activities and outdoor adventures, making it perfect for a city-themed getaway. Explore local attractions such as event venues, urban parks, and nature reserves that cater to cultural and outdoor enthusiasts. Don't miss a visit to the historic Sleepy Hollow Cemetery for a unique experience. Embrace the charm of this quaint area while enjoying its diverse points of interest.

Woodstock Square: A charming square located 27.4km from Sleepy Hollow, Woodstock Square offers a delightful mix of city vibes and historic charm. Stroll through its quaint shops and cafes, and soak in the community atmosphere that has made it a local favourite.
Heritage Park: Situated 25.7km away, Heritage Park is an urban oasis perfect for families. Enjoy its vast green spaces and outdoor activities, making it an ideal spot for picnics, leisurely walks, and bonding with nature in a city setting.
Santa's Village: Just 3.2km from Sleepy Hollow, Santa's Village is a whimsical theme park filled with family-friendly entertainment. Experience festive rides and attractions that bring the magic of Christmas to life all year round.

Best time to go to Sleepy Hollow

The best time to visit Sleepy Hollow can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Sleepy Hollow falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Sleepy Hollow falls in January, visitor numbers are slightly low and weather is mostly cloudy with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	22.3°F (-5.4°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low
February	24.6°F (-4.1°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low
March	37.4°F (3.0°C)	Light Rain	Mostly Cloudy	Average	Average
April	47.3°F (8.5°C)	Light Rain	Mostly Cloudy	Average	Average
May	59.4°F (15.2°C)	Light Rain	Mostly Sunny	Average	Average
June	68.9°F (20.5°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	72.9°F (22.7°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	71.4°F (21.9°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
September	64.9°F (18.3°C)	Light Rain	Mostly Sunny	Average	Average
October	52.5°F (11.4°C)	Light Rain	Mostly Sunny	Average	Average
November	39.4°F (4.1°C)	Light Rain	Mostly Sunny	Average	Average
December	29.5°F (-1.4°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low

Tips to save on your trip to Sleepy Hollow

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
Consider traveling to Sleepy Hollow during the low season (December to February) for more affordable options.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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

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

DoubleTree by Hilton Chicago - Arlington Heights

75 W Algonquin Rd Arlington Heights IL

Fully refundableReserve now, pay when you stay

£89

16 Aug - 17 Aug

includes taxes & fees

Eaglewood Resort and Spa

1401 Nordic Rd Itasca IL

Fully refundableReserve now, pay when you stay

£113

23 Aug - 24 Aug

includes taxes & fees

8.8/10 Excellent! (1,235 reviews)

"Incredible staff. Very friendly. The bar is cool. Room was clean, but bathroom needs to be restored. Old bath and shower head from the 70s. Everything is luxurious except the bathroom."

Reviewed on 28 Jul 2026

DoubleTree by Hilton Libertyville - Mundelein

510 E IL Route 83 Mundelein IL

Fully refundableReserve now, pay when you stay

£101

25 Aug - 26 Aug

includes taxes & fees

8.6/10 Excellent! (1,008 reviews)

"We had black hair in one of the beds and ants in the bathroom. Spoke to the front desk about it and all they did was shrug. Property was a bit of a mess. The weeds needed to be cleaned up out of the landscaping. The hotel could be a beautiful property if it was maintained and updated."

Reviewed on 28 Jul 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.