Sleepy Hollow Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Sleepy Hollow Vacation

Entertainment, history, art and more … There's so much to experience with a Sleepy Hollow vacation package. And with the ability to customize 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, organizing your ultimate tailored Sleepy Hollow vacation is simple with Expedia.

Top Sleepy Hollow Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
Downtown Chicago
Price was CA $2,212, price is now CA $1,404 per person
CA $1,404
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,104 reviews)
Front desk staff Every front desk person was friendly and helpful Room Spacious and Recently updated Location Proximity to CTA is perfect or walkable to attractions, Grant Park etc Amenities 5 stars for on site washer dryer. First time I've ever seen this at a hotel

Reviewed on Aug 5, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,701, price is now CA $1,579 per person
CA $1,579
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (540 reviews)
Great staff, great place!

Reviewed on Aug 5, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $3,677, price is now CA $2,273 per person
CA $2,273
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)
We enjoyed the roof top bar and the glass floor experience in the roof top bar Room was clean and breakfast changed daily In a good area for attractions and transport

Reviewed on Aug 5, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $2,858, price is now CA $1,776 per person
CA $1,776
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,606 reviews)
Our stay was amazing with a beautiful view.

Reviewed on Aug 5, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $2,383, price is now CA $1,573 per person
CA $1,573
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,752 reviews)
Rating: ★★★★★ Stayed: July 31, 2026 My stay at Eurostars Magnificent Mile was excellent. The location is very convenient — the Grand train station is only about a 6‑minute walk, making it easy to get around the city and even reach Wrigley Field without any hassle. The area feels lively, safe, and perfect for exploring Chicago. Breakfast was very good, and the staff was friendly and attentive. I want to highlight Cristina in particular — her service, kindness, and professionalism really stood out and made the experience even better. Even though I was on a high floor, you can still hear some of the typical city noise (motorcycles, ambulances, police sirens). It’s part of being in downtown Chicago, and it didn’t take away from the overall quality of the stay. Overall, this was a great experience from start to finish. I definitely recommend this hotel.

Reviewed on Aug 5, 2026

Ready to book your vacation to Sleepy Hollow?

 

Choose your dates

Sleepy Hollow Hotel Deals

Eaglewood Resort and Spa

Eaglewood Resort and Spa

4 out of 5
1401 Nordic Rd Itasca IL
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from Aug 23 to Aug 24
CA $164
CA $213 total
Aug 23 - Aug 24
includes taxes & fees
8.8/10 Excellent! (1,253 reviews)
"The bowling alley."

Reviewed on Aug 5, 2026

Eaglewood Resort and Spa
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 CA $227 per night from Aug 20 to Aug 21
CA $227
CA $253 total
Aug 20 - Aug 21
includes taxes & fees
8.8/10 Excellent! (1,017 reviews)
"good"

Reviewed on Aug 5, 2026

The Westin Chicago Northwest
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

4 out of 5
1200 N Mittel Blvd Wood Dale IL
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Aug 16 to Aug 17
CA $154
CA $171 total
Aug 16 - Aug 17
includes taxes & fees
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
See all 499 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Sleepy Hollow vacation package cost?
You'll find cheap prices from CA $1,404 on Expedia for your Sleepy Hollow escape. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Sleepy Hollow costs.
What are the cheapest months to go to Sleepy Hollow?
You're likely to find lower prices and greater availability in January, February and November. Browse our cheap Sleepy Hollow vacation packages and you could score some great off-season discounts.
How many days is enough for Sleepy Hollow?
Generally, a handful of days is enough to tick off the main sights during your Sleepy Hollow vacation. However, if you want to have time to chill out or go on day tours, consider extending your trip.
How to find the best Sleepy Hollow package deals?
Use Expedia's filters to find some great Sleepy Hollow package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break 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 vacation package well in advance.
Is it cheaper to book a Sleepy Hollow vacation as a package?
An Expedia vacation package could land you great savings when compared to booking hotels and flights individually. Better still, you can personalize your Sleepy Hollow trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Sleepy Hollow?
If you've got your Sleepy Hollow vacation dates locked in, book early to grab some fantastic deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Sleepy Hollow?

  1. Pick your travel dates: The things you plan to do in Sleepy Hollow and your favourite season will help you decide when to go.
  2. Set your budget: Consider costs such as food, flights and transportation when calculating how much to put aside for your trip to Sleepy Hollow. Then, select a hotel that works with your budget, whether that's a wallet-friendly option or a more luxurious retreat.
  3. Decide how many days away: Start by compiling a list of the activities and sights you want to get to in Sleepy Hollow. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your airfare and accommodations: After you've nailed down your travel dates and duration, book the perfect Sleepy Hollow vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.