Sleepy Hollow Packages (Flight + Hotel)

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Top Sleepy Hollow Flight + Hotel Deals

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

The Emily Hotel

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 5 hours ago
Return flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (1,115 reviews)
Spacious room with a very comfortable bed, comfortable room temperature on a hot weekend, large bathroom and spacious work station. Close to trains that transport to the loop within minutes.

Reviewed on 8 Jul 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 5 hours ago
Return flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
The servers and bartenders at the property were amazing! Gentleman who stored our luggage was polite and extremely attentive!

Reviewed on 16 Jul 2025

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 5 hours ago
Return flight included
Calgary (YYC) to Chicago (ORD)
8.6/10 Excellent! (1,795 reviews)
The TV didn't work and made a hissing sound and the tub took hours to drain after being filled. Not big deals overall, but when I mentionned it a check-out, the staff member only said sorry and did not make a note of the issues. Presumably they will get fixed when someone complains more aggressively.

Reviewed on 15 Jul 2025

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 5 hours ago
Return flight included
Calgary (YYC) to Chicago (ORD)
8.4/10 Very Good! (1,986 reviews)
For a four star hotel in chicago it is very pricy only good for location as the amenities and extras are what you gt in a 3 star hotel outside of the city. The carpet is dated and dusty, the bathroom was clean and more modern than expected, but it is not as expected.

Reviewed on 16 Jul 2025

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 5 hours ago
Return flight included
Calgary (YYC) to Chicago (ORD)
8.4/10 Very Good! (1,773 reviews)
Beautiful historic hotel! Loved the live music in the lobby. I was there in a traditional room sith 2 double beds, and then i upgraded to a suite. Both were nice rooms, but i LOVE a good suite! Personnel at the hotel were kind and helpful. Have a cocktail and a brownie in the lobby- you won't regret it!

Reviewed on 15 Jul 2025

Top hotels in Sleepy Hollow

Grand Royal Hotel O'Hare - Chicago

Grand Royal Hotel O'Hare - Chicago

3.5 out of 5
1000 Busse Rd, Elk Grove Village, IL
Fully refundableReserve now, pay when you stay
The price is ฿3,082 per night from 27 Jul to 28 Jul
฿3,082
฿3,483 total
27 Jul - 28 Jul
includes taxes & fees
5.6/10 (112 reviews)
"Everything working in room. Check in easy and friendly."

Reviewed on 13 Jul 2025

Grand Royal Hotel O'Hare - Chicago
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 ฿3,284 per night from 27 Jul to 28 Jul
฿3,284
฿3,645 total
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very Good! (1,020 reviews)
"Great hotel"

Reviewed on 15 Jul 2025

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
Comfort Inn Chicago Schaumburg - O'Hare Airport

Comfort Inn Chicago Schaumburg - O'Hare Airport

2.5 out of 5
1300 E Higgins Rd, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is ฿2,914 per night from 17 Aug to 18 Aug
฿2,914
฿3,351 total
17 Aug - 18 Aug
includes taxes & fees
7/10 Good! (865 reviews)
"Good"

Reviewed on 14 Jul 2025

Comfort Inn Chicago Schaumburg - O'Hare Airport
See all 486 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.

Frequently asked questions

How much does a Sleepy Hollow holiday package cost?
You can grab a holiday package to this top destination from ฿13,514 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.

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