Sleepy Hollow Packages (Flight + Hotel)

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Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
3 Jul - 7 Jul
Return direct flight included
Las Vegas (LAS) to Chicago (ORD)
8/10 Very Good! (1,023 reviews)
The bathroom could have been cleaner, the air conditioning barely worked which made the room incredibly hot. The lobby is nice enough, and the staff is super friendly. The location is wonderful.

Reviewed on 11 May 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
3 Jul - 7 Jul
Return direct flight included
Las Vegas (LAS) to Chicago (ORD)
9.2/10 Wonderful! (1,190 reviews)
The best hotel hands down!

Reviewed on 13 May 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
3 Jul - 7 Jul
Return direct flight included
Las Vegas (LAS) to Chicago (ORD)
9.4/10 Exceptional! (687 reviews)
Enjoyed our stay at the Pendry. It is in a great location and very walkable. Housekeeping was great. Enjoyed the restaurant and bar and the staff was very friendly.

Reviewed on 15 May 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
3 Jul - 7 Jul
Return direct flight included
Las Vegas (LAS) to Chicago (ORD)
9.2/10 Wonderful! (3,511 reviews)
Location was fantastic and the property is beautiful!

Reviewed on 15 May 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
3 Jul - 7 Jul
Return direct flight included
Las Vegas (LAS) to Chicago (ORD)
8.8/10 Excellent! (207 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on 16 Mar 2024

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 featuring a city

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.

Find hotel + flight trips in Downtown Chicago

Top hotels in Sleepy Hollow

Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ฿3,814 per night from 29 May to 30 May
฿3,814
per night
29 May - 30 May
7.6/10 Good! (2,580 reviews)
"Very clean"

Reviewed on 14 May 2024

Warwick Allerton - Chicago
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ฿5,399 per night from 27 May to 28 May
฿5,399
per night
27 May - 28 May
7.6/10 Good! (6,723 reviews)
"Great location for walking to both museums and Magnificent Mile. Restaurants on site if you don't get out to eat. Late check out (noon)."

Reviewed on 14 May 2024

Congress Plaza Hotel
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ฿7,083 per night from 23 May to 24 May
฿7,083
per night
23 May - 24 May
8.6/10 Excellent! (1,001 reviews)
"We had a wonderful time in Chicago! This property was located in such a great area and easy walking to all the things we wanted to do...and eat. :)"

Reviewed on 10 May 2024

The Westin Michigan Avenue Chicago
See all 4,362 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?
Get your credit card ready, because a getaway to Sleepy Hollow starts from a tempting ฿22,806. 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 holiday 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 holiday?
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 holiday rentals like beachside villas and city apartments. You’ve got choices galore!
Can I choose my airline with a Sleepy Hollow Expedia holiday 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 holiday package?
Certainly, and we’ll help you every step of the way. You may be able to cancel or amend your Sleepy Hollow holiday 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.

Popular places to visit

Image for Wrigley Field

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Image for McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Image for Six Flags Great America

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

Things to do

Image for Spirit of Chicago Signature Dinner Cruise on Lake Michigan

Spirit of Chicago Signature Dinner Cruise on Lake Michigan

฿5,775
Per adult
Spirit of Chicago Signature Dinner Cruise on Lake Michigan
See all activities in Chicago

More trip options

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