
Sleepy Hollow Vacations from $235
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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.
The Latest Sleepy Hollow vacation packages
Price found within the past 48 hours. Click for updated prices.

Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $378, price is now $235 per person
$235
per person
Jan 23 - Jan 25
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
This was our first time at Level Chicago -Old Town. Last year we stayed at Level Chicago - North. Both apartments were really cozy and offered amazing views of the city. Old Town is a great place to stay, the staff overall was professional and polite. The unit was mostly clean, however, some of the towel were stained (seemed like he make up did not come off with bleach). It wasn't to my liking so I did not use them. Also, they knew we were six people but only gave 4 bath towels. I had to request additional. Another thing is that the locks in the bathroom and bedrooms were not working. It was a bit frustrating considering 6 people were sharing one bathroom.
The apartment itself is very comfortable, has washer and dryer on site, which is convenient, especially when staying with children. The kitchen was equipped with all the basic needs except a good coffee machine. They have a nespresso machine but I would have rather an actual coffee machine not espresso machine.
Safety was key. My family and I felt safe in the building and the area. Parking was not available in the building (the cost is $70 per night) but that wasnt an issue because we found plenty of parking right outside by the meters.
Reviewed on Oct 29, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $635, price is now $351 per person
$351
per person
Jan 1 - Jan 4
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.
Reviewed on Oct 28, 2025


Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $549, price is now $330 per person
$330
per person
Jan 16 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
Great staff, very clean rooms, overall great experience
Reviewed on Oct 31, 2025

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $515, price is now $320 per person
$320
per person
Jan 1 - Jan 4
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Loved my stay here. Everything was top notch from the time I entered the lobby. The staff was welcoming and enthusiastic about you choosing to patronize their hotel. The check-in process was quick. The hotel’s rooms were very clean and had the latest amenities. Televisions had numerous channel options. The roof top bar was amazing for photo ops. It’s also in a very good location for site seeing & shopping.
Reviewed on Oct 31, 2025
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DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
1200 N Mittel Blvd, Wood Dale, IL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $99 total per night from Nov 23 to Nov 24
$99 total
Nov 23 - Nov 24
Total with taxes and fees
8/10 Very Good! (1,072 reviews)
Room was huge and had everything! Ray at check in was super friendly asnd professional. Location is great. An unexpectedly pleasant stay!
Reviewed on Oct 29, 2025

Wyndham Garden Schaumburg Chicago Northwest
1725 E Algonquin Road, Schaumburg, IL
Fully refundableReserve now, pay when you stay
$58 nightly
The price is $67 total per night from Nov 27 to Nov 28
$67 total
Nov 27 - Nov 28
Total with taxes and fees
6.4/10 (1,018 reviews)
Great
Reviewed on Oct 28, 2025

Eaglewood Resort and Spa
1401 Nordic Rd, Itasca, IL
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $144 total per night from Dec 1 to Dec 2
$144 total
Dec 1 - Dec 2
Total with taxes and fees
8.6/10 Excellent! (1,027 reviews)
100/10 recommend!
I stayed friday-sunday and I had to switch rooms on Saturday due to my tub filling up/backing up as I took a shower but they waived the entire resort fee so I'm still sticking to my word that everything was perfect, rooms were very clean and peaceful, it felt like home away from home and I'll definitely ...
Reviewed on Oct 27, 2025
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.
Find the Best Sleepy Hollow Vacation Packages
Sleepy Hollow Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 3,300 |
Top Sights | Santas Village, Hemmens Cultural Center and Epic Air Trampoline Park |
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