Sleepy Hollow Holidays from £612

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to £335 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

    Packages with flights are ATOL protected

Your Sleepy Hollow Holiday

Make travel planning hassle-free by snapping up a holiday package to Sleepy Hollow. Let us handle the minutiae, so you can focus on savouring everything this neighbourhood has to offer. Your trip to Sleepy Hollow wouldn't be complete without exploring leading attractions nearby such as Morton College, Hawthorne Works Museum and Balzekas Museum of Lithuanian Culture. Whatever your travel plans or the size of your budget, booking your ideal Sleepy Hollow holiday is simple with Expedia.

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was £972, price is now £612 per person
£612
per person
8 Nov - 13 Nov
found 24 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
I enjoyed my stay here

Reviewed on 23 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,400, price is now £838 per person
£838
per person
8 Nov - 13 Nov
found 24 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,738, price is now £1,078 per person
£1,078
per person
8 Nov - 13 Nov
found 24 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug 2025

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,683, price is now £1,074 per person
£1,074
per person
8 Oct - 12 Oct
found 13 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,014 reviews)
Loved the hotel. Very clean and comfortable. The gentleman who checked us out was not the most friendly, but everyone else was super helpful!

Reviewed on 18 Aug 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,560, price is now £1,002 per person
£1,002
per person
23 Sept - 29 Sept
found 11 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (666 reviews)
Everything was great

Reviewed on 23 Aug 2025

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

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

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £131 per night from 1 Sept to 2 Sept
£131
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,210 reviews)
"The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude ..."

Reviewed on 20 Aug 2025

The Wade
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 £94 per night from 25 Aug to 26 Aug
£94
25 Aug - 26 Aug
includes taxes & fees
7.8/10 Good! (8,995 reviews)
"Transportation by bus or subway is within a 5 minute walk, very easy. Hotel is across from a beautiful park. Lobby is nice but the hallways look very rough. It’s an old hotel with basic upgrades. Rooms were clean but shows it age. Beds were comfy. We checked our luggage upon arrival because our room ..."

Reviewed on 23 Aug 2025

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £132 per night from 3 Sept to 4 Sept
£132
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,752 reviews)
"Great location. Nice size rooms. Breakfast was really good, only way to busy and crowded during that experience. They should extend the breakfast hours by an hour to reduce the over crowding. Overall good stay. Would return.."

Reviewed on 23 Aug 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,828 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Sleepy Hollow travel package cost?
Get your credit card ready, because a trip to Sleepy Hollow starts from an enticing £612. When you combine your flights, hotels and more into a travel package, you'll land the best prices.
If I'm not able to travel, can I cancel my Sleepy Hollow travel package?
Because we know life is full of surprises, the answer is yes. For more information, check out our Customer Service Portal. But generally speaking, if you've made your booking in the last 24 hours, you may be able to change or cancel it for free. Your hotel, airline or car rental company may charge a fee if you made your booking a while ago.
How do I get a cheap travel package to Sleepy Hollow?
Booking a Sleepy Hollow travel package with Expedia is a simple way to save. We offer more than 550 partner airlines and 1,000,000 hotels worldwide. With such a wonderful range to pick from, you'll have no difficulty creating your ideal holiday.
Does Expedia offer Book Now, Pay Later Sleepy Hollow holidays?
Expedia has teamed up with online lender Klarna to make booking your next break easier on your hip pocket. Paying in instalments means you can spread the costs of your dream holiday, leaving you with more cash to spend while you're travelling. Klarna has several payment plans to choose from, so you're sure to find one that fits your budget. Browse these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month sounds right for you, Klarna offers just that! Paying in convenient monthly instalments will make your getaway dreams come true.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay off your holiday across multiple transactions.
  • Low deposit holidays: When you stumble on an incredible deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you lock in your escape.

Where should I stay in Sleepy Hollow?
Make sightseeing easy by staying near Sleepy Hollow's biggest attractions. Millennium Park and Wrigley Field are two traveller favourites.
What are the top hotels in Sleepy Hollow?
Get your escape off to a good start by reserving a room at Hyatt Regency Chicago. It's one of most popular properties in Sleepy Hollow. Another comfortable option is The Godfrey Hotel Chicago.
How far in advance should I book my Sleepy Hollow holiday?
To land rock-bottom prices, book ASAP. Airlines usually start selling tickets, along with some of the lowest fares, around a year prior to departure. Hotels, car rental and experiences should also be booked early so you can have the pick of the bunch. If you're in need of a last-minute getaway to Sleepy Hollow, there are always lots of great deals on Expedia. Book your escape today!
What does an Expedia Sleepy Hollow travel package include?
Flights, hotels and rental cars — we've got them covered. With Expedia, you can create your Sleepy Hollow package just the way you want. All you have to do is decide just what you need. Once you've made your booking, you can add on extras like experiences and activities. The more you bundle, the greater the savings!
What should I know before booking a Sleepy Hollow travel package?
Our prices are already low. However, you'll snap up even more savings when you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and lots of choice.
Can I choose my airline with a Sleepy Hollow Expedia travel package?
Most definitely. Expedia has access to more than 550 partner airlines across the globe, so you can customize your Sleepy Hollow escape according to your style and budget.

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

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

Wrigley Field
Magnificent Mile - River North which includes street scenes, signage and night scenes

Michigan Avenue

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

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

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

£31
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
96% of travellers recommend
Chicago By Night River & 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. Flight-inclusive packages are ATOL protected.