Sleepy Hollow Holidays from AU$3,287

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Your Sleepy Hollow Holiday

Experience everything this neighbourhood has to offer with a tailor-made Sleepy Hollow holiday package. However you picture yourself spending your time here, you'll find endless opportunities for fun, relaxation and adventure. What to cross off your itinerary first? Nearby Balzekas Museum of Lithuanian Culture is one thing you can't miss during your trip to Sleepy Hollow. Expedia will help turn your dream Sleepy Hollow holiday into reality, whatever your travel plans or budget.

Top Holiday Package Deals in Sleepy Hollow

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
AU$3,287
per person
27 Dec - 3 Jan
found 16 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
I traveled from Cincinnati Ohio and the room on the 36th floor had a great view of Lake Michigan. Valet staff for parking was excellent as well. Highly recommended if you’re planning to visit Chicago.

Reviewed on 19 Oct 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
AU$4,794
per person
27 Dec - 3 Jan
found 16 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
AU$3,806
per person
27 Dec - 3 Jan
found 16 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (2,727 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
AU$3,334
per person
27 Dec - 3 Jan
found 16 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (576 reviews)
Pendry Chicago

Pendry Chicago

Downtown Chicago
AU$3,825
per person
27 Dec - 3 Jan
found 16 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,163 reviews)
A tried and tested hotel that I love for business travel

Reviewed on 19 Oct 2026

Our guide on 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
A busy city street with tall buildings, a bus, and cars.

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 hotels in Downtown Chicago
A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

Find hotels in Magnificent Mile
A river with yellow boats, a bridge, and tall buildings.

The Loop

Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.

Find hotels in The Loop
A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

Find hotels in River North
A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Find hotels in Lincoln Park

Our pick of the best Sleepy Hollow Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
AU$181
10 Nov - 11 Nov
includes taxes & fees
Congress Plaza Hotel
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
AU$260
1 Nov - 2 Nov
includes taxes & fees
8.8/10 Excellent! (5,554 reviews)
"Close to everything. Property itself a little outdated. The bathroom was uncomfortable."

Reviewed on 19 Oct 2026

River Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
AU$206
11 Nov - 12 Nov
includes taxes & fees
8/10 Very good! (2,537 reviews)
"Stayed for 3 days, and it was great! The staff was super kind when helping me after I accidentally selected the wrong type of room.It was cozy and breakfast was great! I’d stay again 😄"

Reviewed on 19 Oct 2026

The Chicago Hotel Collection Ambassador Gold Coast
See all 4,846 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays
family friendly holidays
Family Friendly Holidays
Family Friendly Holidays
golf holidays
Golf Holidays
Golf Holidays
luxury holidays
Luxury Holidays
Luxury Holidays
romantic holidays
Romantic Holidays
Romantic Holidays
ski holidays
Ski Holidays
Ski Holidays
honeymoon holidays
Honeymoon Holidays
Honeymoon Holidays
pet friendly holidays
Pet-friendly Holidays
Pet-friendly Holidays
Spa Holidays
Spa Holidays
Spa Holidays

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 AU$3,287. 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 homes 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.

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

AU$56
per adult
92% of travellers recommend
Art Institute of Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$57
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.