Sleepy Hollow Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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
- Sheraton Grand Chicago Riverwalk
Jan 21 - Jan 24Sheraton Grand Chicago Riverwalk + Flight
Downtown Chicago3 nights4.0 star property8.6/10 - Excellent (1,881 reviews)Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • 1 stop ORD - YYZ • NonstopCA $1,134CA $822found 11 hours agoper traveller - The Peninsula Chicago
Jan 8 - Jan 11The Peninsula Chicago + Flight
Downtown Chicago3 nights5.0 star property9.8/10 - Exceptional (1,008 reviews)Roundtrip • Montreal (YUL) - Chicago (ORD)YUL - ORD • 1 stop ORD - YUL • 1 stopCA $2,118CA $1,439found 20 hours agoper traveller - Level Chicago Fulton Market
Jan 1 - Jan 7Level Chicago Fulton Market + Flight
Downtown Chicago6 nights4.0 star property9.2/10 - Wonderful (604 reviews)"Weird space w the way the bed is no access off the side and the counter was stained badly. There was a 28$ additional amenity fee that they slapped on upon check in. The pool is closed and didn’t use the weight room it was a one night stay. over priced but could be ok for a long stay w the kitchen"Reviewed November 6, 2026Roundtrip • Montreal (YUL) - Chicago (ORD)YUL - ORD • 1 stop ORD - YUL • NonstopCA $1,693CA $1,262found 1 day agoper traveller - The Blackstone, Autograph Collection
Dec 28 - Jan 1The Blackstone, Autograph Collection + Flight
Downtown Chicago4 nights4.0 star property9.0/10 - Wonderful (1,003 reviews)"Nice property but a little worn.mattresses were not that comfortable .Some staff were great, others not so much."Reviewed November 8, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YTZ • NonstopCA $1,195CA $897found 1 day agoper traveller - The Talbott, Autograph Collection
Dec 28 - Jan 1The Talbott, Autograph Collection + Flight
Downtown Chicago4 nights4.5 star property9.4/10 - Exceptional (195 reviews)"Hotel was very nice and clean. The location was excellent."Reviewed November 8, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YTZ • NonstopCA $1,144CA $864found 1 day agoper traveller
Sleepy Hollow Hotel Deals
Best Western Plus Elgin - Chicago
Best Western Plus Elgin - Chicago"Everything was so good."
Holiday Inn Chicago Northwest-Elgin by IHG
Holiday Inn Chicago Northwest-Elgin by IHG
Country Inn & Suites by Radisson, Elgin, IL
Country Inn & Suites by Radisson, Elgin, IL
Comfort Suites Elgin Northwest
Comfort Suites Elgin Northwest"Wonderful friendly and helpful staff. Very clean and well maintained hotel. Room was nice and bed comfortable. Breakfast had lots of options. Great location easy access to tollway. Close to huge selection of restaurants and shopping."
Holiday Inn Express & Suites Chicago - Hoffman Estates by IHG
Holiday Inn Express & Suites Chicago - Hoffman Estates by IHG
"Great stay!"
Frequently Asked Questions
How much does a Sleepy Hollow vacation package cost?
You'll find cheap prices from CA $822 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?
- Pick your travel dates: The things you plan to do in Sleepy Hollow and your favourite season will help you decide when to go.
- 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.
- 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.
- Bundle your airfare and accommodations: After you've nailed down your travel dates and duration, book the perfect Sleepy Hollow vacation package for you.