Sleepy Hollow Vacation Packages
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Top Holiday Package Deals in Sleepy Hollow
Price found within the past 48 hours. Click for updated prices.
The Chicago Hotel Collection - Wrigleyville
Lakeview
CA $1,018
per person
Oct 21 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
7.2/10 Good! (1,023 reviews)
We ended up staying here on short weekend trip (3 friends) and really enjoyed it! Location was fantastic with easy L train access. The hotel is staffed and available but they aren’t always visible which can be a bit tricky when you need something quickly like towels.
The street itself, which houses many famed and fun bars alongside Wrigley Field is a great perk, however if you are traveling with small children it may be a bit too crowded and rowdy on a weekend or game day.
All in all, our room and overall stay was fantastic. Super clean, super convenient!
Reviewed on Aug 29, 2026
Level Chicago - River North
Downtown Chicago
CA $1,628
per person
Oct 13 - Oct 17
found 4 hours ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.2/10 Wonderful! (1,055 reviews)
Very nice hotel, the view was nice the room was clean and staff was very helpful definitely recommend!
Reviewed on Aug 29, 2026
Wrigleyville Inn
Lakeview
CA $2,105
per person
Nov 15 - Nov 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
10/10 Exceptional! (28 reviews)
Absolutely loved staying here, and would stay again! Beautiful view rooms, provided everything you needed, close to plenty of dining, and able to walk to Wrigley!
Reviewed on Jul 26, 2026
Where to stay in Sleepy Hollow
Find the best Sleepy Hollow areas and neighborhoods for the activities you enjoy most. Learn more about Sleepy Hollow
Downtown Chicago
4 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Sleepy Hollow Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $148
CA $176 total
Sep 8 - Sep 9
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $199
CA $236 total
Aug 31 - Sep 1
includes taxes & fees
8/10 Very good! (2,122 reviews)
"The room was very clean but I think our floor was being renovated so floor was clean looking and smelled. The drainage in sink and shower was terrible also the walls were super thin and could hear everything in the rooms next door. Breakfast buffet was wonderful and a good variety. The staff was ..."
Reviewed on Aug 29, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $324
CA $381 total
Sep 18 - Sep 19
includes taxes & fees
8.4/10 Very good! (2,457 reviews)
"Checking in and out was a breeze"
Reviewed on Aug 29, 2026
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 vacation package cost?
Get your credit card ready, because a getaway to Sleepy Hollow starts from a tempting CA $1,018. When you bundle your flights, hotels and more into a package, you'll land the lowest prices.
How do I get a cheap travel package to Sleepy Hollow?
Book everything in the one place with our Sleepy Hollow vacation packages. We have incredible bargains on hotels, flights, tours and more that'll keep your travel budget happy and your adventurous spirit alive. And, with more than 550 partner airlines and 1,000,000 hotel options around the world to pick from, there are endless opportunities to mix and match as you like.
Where should I stay in Sleepy Hollow?
There's plenty to do in Sleepy Hollow, so stay near its best attractions and spend more time sightseeing. Balzekas Museum of Lithuanian Culture is one spot to put on your must-see list.
How far in advance should I book my Sleepy Hollow vacation?
Reserving your flights early with Expedia means one less thing to worry about. A number of air carriers advertise prices up to 12 months in advance. This is usually the cheapest time to book. If circumstances have left you booking late, fantastic last-minute deals to Sleepy Hollow sometimes emerge a few weeks before departure.
What does an Expedia Sleepy Hollow travel package include?
Expedia has everything you need to lock in Sleepy Hollow trip, but what goes into your package is your call. Select from any combination of rental cars, flights and hotels. Chasing some experiences or tours to keep you on the go? Once you've made your booking, you can add them on too. No matter your style, there's a package to meet your needs.
What should I know before booking a Sleepy Hollow travel package?
Booking all the parts of your getaway together is a great way to save. Bundle your airfares, rental cars and hotels into a neat package. But your options don't end at hotels. Expedia has all kinds of properties, including vacation rentals like beachside villas and city apartments. You've got choices galore!
Can I choose my airline with a Sleepy Hollow Expedia vacation package?
Expedia has access to more than 550 airline partners worldwide, so you definitely can. Simply select the carrier that suits you and craft your ideal Sleepy Hollow getaway.
If I'm not able to travel, can I cancel my Sleepy Hollow vacation package?
Certainly, and we'll help you every step of the way. You may be able to cancel or amend your Sleepy Hollow vacation package at no cost if you booked in the last 24 hours. But you may incur a fee from your hotel, airline or car rental company for older bookings. If your travel plans unexpectedly change, have a look at our Customer Service Portal for more information.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
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- Visit The Loop
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.