Sleepy Hollow Holidays

Sleepy Hollow Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Omni Chicago Hotel
Trump International Hotel & Tower Chicago
Kinzie Hotel
Le Méridien Essex Chicago

Things to do near Sleepy Hollow

Sleepy Hollow is perfect for family-friendly outdoor adventures and urban exploration. Visitors can enjoy various activities, including shopping at local centres, attending live music events, and exploring new attractions. Don't miss out on the festive Halloween night celebrations and seasonal attractions that add to the charm of this quaint destination. Fun tours are also available, ensuring an enjoyable experience for all ages.

Shopping

Cabela's, located 8.0km from Sleepy Hollow, offers a fantastic selection of outdoor gear and gifts. If you're up for a drive, Charlestowne Mall and Village Square Shopping Center, both 19.3km away, provide a vibrant mix of shopping, dining, and entertainment for the whole family.

Recreation

The Arcada Theater, located 20.9km from Sleepy Hollow, offers a captivating blend of romance and culture through its diverse performances. Similarly, the Steel Beam Theater, also 20.9km away, provides a charming atmosphere for family entertainment. For a more local experience, Cinemark West Dundee, just 483m away, is perfect for a family movie outing.

Adventure

Experience the thrill of Epic Air Trampoline Park, located 12.9km from Sleepy Hollow, where you can bounce around in an exciting arcadeAdventureZone. For nature lovers, the scenic Spring Lake Valley Forest Preserve Trailhead, 8.0km away, offers picturesque hiking trails, while Algonquin Lakes Trailhead, 6.4km away, beckons with its outdoor adventure vibes.

Nightlife

Sleepy Hollow boasts a quaint yet vibrant nightlife. Visit The Village Squire for hearty pub fare and a warm atmosphere. For a laid-back evening, enjoy craft beers at the nearby Sleepy Hollow Brewing Company, where local musicians often perform, creating a cheerful ambience for all.

*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, is an ideal destination for families and outdoor enthusiasts, offering a delightful mix of urban parks, event venues, and nature reserves. Visitors can immerse themselves in local culture while exploring attractions like the Sleepy Hollow Cemetery. This charming locale promises a memorable experience for all types of travellers seeking a blend of relaxation and adventure in a picturesque setting.

  • Fox River Preserve: Located 17.7km from Sleepy Hollow, this park offers a serene escape into nature. With its eco-friendly atmosphere, visitors can enjoy family-friendly activities such as hiking, birdwatching, and picnicking amidst beautiful landscapes along the Fox River.
  • Santa's Village: Just 3.2km away, this enchanting theme park is perfect for families seeking fun and entertainment. With festive rides, engaging attractions, and seasonal events, Santa's Village brings the magic of Christmas to life all year round.
  • NOW Arena: Situated 8.0km from Sleepy Hollow, this entertainment facility hosts exciting events and performances. Families can enjoy thrilling sports matches, concerts, and various shows, making it a vibrant hub for local entertainment.

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.

Top hotels in Sleepy Hollow

Sheraton Suites Chicago Elk Grove

Sheraton Suites Chicago Elk Grove

3.5 out of 5
121 Northwest Point Boulevard Elk Grove Village IL
Fully refundableReserve now, pay when you stay
The price is S$143 per night from 5 Jul to 6 Jul
S$143
5 Jul - 6 Jul
includes taxes & fees
8/10 Very good! (1,019 reviews)
"The room was hot when arrived. We had to get fans from the lobby. The water was shut off without any notice. The elevator took forever because one of the elevator’s was broken. Wouldn’t stay there again."

Reviewed on 29 Jun, 2026

Sheraton Suites Chicago Elk Grove
Hyatt Place Itasca

Hyatt Place Itasca

3 out of 5
1150 North Arlington Heights Road Itasca IL
Fully refundableReserve now, pay when you stay
The price is S$157 per night from 26 Jul to 27 Jul
S$157
26 Jul - 27 Jul
includes taxes & fees
8.8/10 Excellent! (1,179 reviews)
"It was great experience."

Reviewed on 29 Jun, 2026

Hyatt Place Itasca
The Westin Chicago Northwest

The Westin Chicago Northwest

4 out of 5
400 Park Blvd Itasca IL
Fully refundableReserve now, pay when you stay
The price is S$215 per night from 5 Jul to 6 Jul
S$215
5 Jul - 6 Jul
includes taxes & fees
8.8/10 Excellent! (1,012 reviews)
"Clean room, housekeeper didn’t want to give new towels"

Reviewed on 29 Jun, 2026

The Westin Chicago Northwest
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.

What to do in Sleepy Hollow

Frequently asked questions

How much does a Sleepy Hollow holiday package cost?
You can grab a holiday package to this top destination from S$502 on Expedia. However, how much your holiday to Sleepy Hollow costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Sleepy Hollow?
January, February and November are the best times to search for cheap Sleepy Hollow holiday packages. Choosing to travel in less busy months means you can typically find reduced prices on flights and hotels.
How many days is enough for Sleepy Hollow?
The ideal duration of your Sleepy Hollow holiday depends on what you'd like to do and see. Typically, a few days to a week will give you time to visit all the leading sights and discover some hidden gems along the way.
How to find the best Sleepy Hollow package deals?
Use Expedia's filters to find some great Sleepy Hollow package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Sleepy Hollow package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your holiday package as early as possible.
Is it cheaper to book a Sleepy Hollow holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging stays and flights individually. Better still, you can personalise your Sleepy Hollow escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a holiday package to Sleepy Hollow?
If you have your Sleepy Hollow holiday dates finalized, book as soon as you can to bag some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are great for quick escapes.
How to plan a trip to Sleepy Hollow?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Sleepy Hollow.
  2. Set your budget: Consider expenses such as transportation, flights and meals when working out how much to put aside for your trip to Sleepy Hollow. Then, select a hotel that matches your budget, whether that's an affordable stay or a deluxe getaway.
  3. Decide how long to go away for: Now that you're more familiar with Sleepy Hollow, you can work out the ideal length of your holiday. Create a rough plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a personalised Sleepy Hollow holiday package.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.