Sleepy Hollow Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Sleepy Hollow Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Sonesta Chicago O'Hare Airport Rosemont

Sonesta Chicago O'Hare Airport Rosemont

3 out of 5
O'Hare
per person
10 Oct - 13 Oct
found 1 day ago
Return flight included
Fort Lauderdale (FLL) to Chicago (ORD)
8.6/10 Excellent! (1,537 reviews)
Sonesta was lovely. Easy check in. Nice room. Pillows not so great. Shuttle service was excellent as was all the staff!

Reviewed on 8 Aug, 2025

Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
O'Hare
per person
10 Oct - 13 Oct
found 1 day ago
Return flight included
Fort Lauderdale (FLL) to Chicago (ORD)
8.8/10 Excellent! (1,001 reviews)
Food is good, like most other hotels. We like waffle particularly.

Reviewed on 13 Aug, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
O'Hare
per person
10 Oct - 13 Oct
found 1 day ago
Return flight included
Fort Lauderdale (FLL) to Chicago (ORD)
8.6/10 Excellent! (2,367 reviews)
Only 1 elevator was seemingly working so it took like 10 minutes every time you wanted to use one. People in the hallways were so noisy and slamming doors at all hours and the general look and appearance of the hotel seemed worse for wear. Definitely need to invest in some major renovations and upgrades.

Reviewed on 10 Aug, 2025

Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
O'Hare
per person
10 Oct - 13 Oct
found 1 day ago
Return flight included
Fort Lauderdale (FLL) to Chicago (ORD)
8.8/10 Excellent! (2,250 reviews)
The hotel was safe and clean.

Reviewed on 13 Aug, 2025

Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare

3.5 out of 5
O'Hare
per person
10 Oct - 13 Oct
found 1 day ago
Return flight included
Fort Lauderdale (FLL) to Chicago (ORD)
8.4/10 Very Good! (1,005 reviews)
Everything was perfect cool clean and respectful . Need more restaurants and fir Starbucks to close at 7 pm since there is only one restaurant to go too if don’t want to go out since we have no car

Reviewed on 11 Aug, 2025

Top hotels in Sleepy Hollow

Hyatt Regency Schaumburg Chicago

Hyatt Regency Schaumburg Chicago

4 out of 5
1800 East Golf Rd, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is S$175 per night from 24 Aug to 25 Aug
S$175
24 Aug - 25 Aug
includes taxes & fees
8.4/10 Very Good! (1,200 reviews)
"Rooms were clean however the bathroom was a little tight for a small family of 3. You can tell they renovated recently which is a plus. Would stay here again if needed to."

Reviewed on 11 Aug, 2025

Hyatt Regency Schaumburg 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 S$139 per night from 24 Aug to 25 Aug
S$139
24 Aug - 25 Aug
includes taxes & fees
8.2/10 Very Good! (1,009 reviews)
"Good"

Reviewed on 11 Aug, 2025

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
DoubleTree by Hilton Chicago - Arlington Heights

DoubleTree by Hilton Chicago - Arlington Heights

4 out of 5
75 W Algonquin Rd, Arlington Heights, IL
Fully refundableReserve now, pay when you stay
The price is S$133 per night from 24 Aug to 25 Aug
S$133
24 Aug - 25 Aug
includes taxes & fees
8/10 Very Good! (1,008 reviews)
"Hotel was well cleaned for its age, but was definitely aging. Some of the front desk staff was less than pleasant, but not everyone."

Reviewed on 6 Aug, 2025

DoubleTree by Hilton Chicago - Arlington Heights
See all 482 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 S$681 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. 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.