Sleepy Hollow Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ฿27,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Jul 2 - Jul 5

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.2/10 - Very good (2,730 reviews)
    "Overall it was a great experience at Felix, everyone was very friendly and helpful, the store in the lobby is convenient and fairly priced and the room was clean and comfortable. Zero complaints. Will be back again for sure."
    Reviewed May 26, 2026
    Return • Los Angeles (LAX) - Chicago (ORD)
    LAX - ORD • Direct ORD - LAX • Direct
    ฿30,557
    ฿23,776
    per traveller
    found 4 hours ago
    Hotel Felix River North/Magnificent Mile
  • Front of property
    Jul 2 - Jul 5

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (4,252 reviews)
    "This hotel is amazing, Great location, super clean and stuff was kind, informative and very respectful! The breakfast was well organized considering the amount people served! Not a missing items at any moment! The rooftop bar was very pleasant place to sit and chill. Strongly recommended!!!"
    Reviewed May 26, 2026
    Return • Los Angeles (LAX) - Chicago (ORD)
    LAX - ORD • Direct ORD - LAX • Direct
    ฿39,884
    ฿28,807
    per traveller
    found 4 hours ago
    Hotel Riu Plaza Chicago
  • Indoor wedding
    Jul 2 - Jul 5

    Swissotel - Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.0/10 - Wonderful (3,348 reviews)
    "Excellent location, walk to all major attractions. Friendly staff. Hotel room was very clean and comfortable. Price was pretty reasonable"
    Reviewed May 26, 2026
    Return • Los Angeles (LAX) - Chicago (ORD)
    LAX - ORD • Direct ORD - LAX • Direct
    ฿32,834
    ฿25,119
    per traveller
    found 4 hours ago
    Swissotel - Chicago
  • Breakfast, lunch, dinner and brunch served
    Jul 2 - Jul 5

    The Royal Sonesta Chicago River North + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (2,605 reviews)
    "Excellent place to stay. Very clean, nice, and very close to everything."
    Reviewed May 25, 2026
    Return • Los Angeles (LAX) - Chicago (ORD)
    LAX - ORD • Direct ORD - LAX • Direct
    ฿32,450
    ฿25,565
    per traveller
    found 4 hours ago
    The Royal Sonesta Chicago River North
  • Executive lounge
    Jul 2 - Jul 5

    Fairmont Chicago at Millennium Park + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    8.8/10 - Excellent (2,170 reviews)
    "Amazing view and clean room"
    Reviewed May 25, 2026
    Return • Los Angeles (LAX) - Chicago (ORD)
    LAX - ORD • Direct ORD - LAX • Direct
    ฿31,985
    ฿25,320
    per traveller
    found 4 hours ago
    Fairmont Chicago at Millennium Park

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

Downtown Chicago

5 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 hotels in Downtown Chicago

Top hotels in Sleepy Hollow

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is ฿4,388 per night from 27 May to 28 May
฿4,388
฿5,216 total
27 May - 28 May
includes taxes & fees
8/10 Very Good! (10,141 reviews)
"Everything was perfect. Great customer service."

Reviewed on 25 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is ฿7,759 per night from 16 Jun to 17 Jun
฿7,759
฿10,151 total
16 Jun - 17 Jun
includes taxes & fees
9.4/10 Exceptional! (4,252 reviews)
"This hotel is amazing, Great location, super clean and stuff was kind, informative and very respectful! The breakfast was well organized considering the amount people served! Not a missing items at any moment! The rooftop bar was very pleasant place to sit and chill. Strongly recommended!!!"

Reviewed on 26 May 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is ฿6,175 per night from 3 Jun to 4 Jun
฿6,175
฿7,342 total
3 Jun - 4 Jun
includes taxes & fees
7.8/10 Good! (1,476 reviews)
"The room was clean and staffs were approachable. Hotel is close to nearby restaurants and shops."

Reviewed on 25 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,855 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 . 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

Wrigley Field

Wrigley Field

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

Wrigley Field
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

฿874
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

฿1,424
per adult
94% of travellers recommend
Skydeck - Willis Tower Admission
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

฿3,569
per adult
90% of travellers recommend
Chicago C3® by CityPASS®
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.