Sleepy Hollow Holidays

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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
Downtown Chicago

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

Our pick of the best Sleepy Hollow Hotel Deals

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$224 per night from 25 May to 26 May
NZ$224
25 May - 26 May
includes taxes & fees
8.2/10 Very Good! (2,699 reviews)
Small room but perfect for one person. Lovely modern bathroom. Good fitness room. Super friendly and helpful front desk staff

Reviewed on 10 May 2026

Hotel Felix River North/Magnificent Mile
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 NZ$266 per night from 12 May to 13 May
NZ$266
12 May - 13 May
includes taxes & fees
8/10 Very Good! (10,203 reviews)
Facilities were clean and the room had what we needed. Doors could be insulated better to reduce sound at the floor-to-door area. Neighbors were very loud waking us up several times. Security was called and promptly responded. Followed their word saying they would remove the guests if it happened ...

Reviewed on 10 May 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$303 per night from 26 May to 27 May
NZ$303
26 May - 27 May
includes taxes & fees
8.8/10 Excellent! (5,193 reviews)
Bar soap was not very effective. Shower curtain leaked water through whole bathroom.

Reviewed on 10 May 2026

River Hotel
See all 4,853 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 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.

Discover the most popular places to visit in Sleepy Hollow

Wrigley Field

Wrigley Field

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$46
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

NZ$75
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

NZ$78
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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.