Sleepy Hollow Holidays from £1,023

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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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,023
per person
21 Nov - 28 Nov
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Great location and helpful staff! Will stay here again!

Reviewed on 11 Sept 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
Save 100% on your flight
£1,684
per person
17 Oct - 23 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
I enjoyed my stay at the Emily. Staff were friendly throughout my stay. I love the brand used for shower gel and shampoo. The only thing I would change, is the location of the full body mirror. I need to be able to back up and see myself. The bed restricted that and the flare from the window made it difficult to look at myself in daylight. Other than that, I’d stay there again. My first time in Chicago (thanks to Kanye) and I’m thrilled that my research brought me to the Emily.

Reviewed on 11 Sept 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
£1,498
per person
17 Oct - 23 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
Save 100% on your flight
£1,429
per person
17 Oct - 23 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
8.2/10 Very good! (3,012 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
£1,609
per person
17 Oct - 23 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,681 reviews)
Amazing place to stay

Reviewed on 11 Sept 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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.3°F (-5.4°C)Light RainMostly CloudySlightly LowSlightly Low
February24.6°F (-4.1°C)Light RainMostly CloudySlightly LowSlightly Low
March37.4°F (3.0°C)Light RainMostly CloudyAverageAverage
April47.3°F (8.5°C)Light RainMostly CloudyAverageAverage
May59.4°F (15.2°C)Light RainMostly SunnyAverageAverage
June68.9°F (20.5°C)Light RainMostly SunnySlightly HighSlightly High
July72.9°F (22.7°C)Light RainMostly SunnySlightly HighSlightly High
August71.4°F (21.9°C)Light RainMostly SunnySlightly HighSlightly High
September64.9°F (18.3°C)Light RainMostly SunnyAverageAverage
October52.5°F (11.4°C)Light RainMostly SunnyAverageAverage
November39.4°F (4.1°C)Light RainMostly SunnyAverageAverage
December29.5°F (-1.4°C)Light RainMostly CloudySlightly LowSlightly 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.

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

Eaglewood Resort and Spa

Eaglewood Resort and Spa

1401 Nordic Rd Itasca IL
£117
13 Sept - 14 Sept
includes taxes & fees
Eaglewood Resort and Spa
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

1200 N Mittel Blvd Wood Dale IL
Fully refundableReserve now, pay when you stay
£92
11 Oct - 12 Oct
includes taxes & fees
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
Hyatt Regency Schaumburg Chicago

Hyatt Regency Schaumburg Chicago

1800 East Golf Rd Schaumburg IL
Fully refundableReserve now, pay when you stay
£108
11 Oct - 12 Oct
includes taxes & fees
Hyatt Regency Schaumburg Chicago
See all 494 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
Golf Holidays
Golf Holidays
Luxury Holidays
Luxury Holidays
gay friendly holidays
LGBTQ+ Holidays
LGBTQ+ Holidays
Romantic Holidays
Romantic Holidays
Ski Holidays
Ski Holidays
Pet Friendly Holidays
Pet Friendly Holidays
Holiday in Month
Where to go when
Where to go when

What to do in Sleepy Hollow

Private Indian-Mexican Fusion Cooking Class in a Chicago Home

Private Indian-Mexican Fusion Cooking Class in a Chicago Home

£72
per adult
Private Indian-Mexican Fusion Cooking Class in a Chicago Home
See all activities in Sleepy Hollow

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.

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* 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.