Sleepy Hollow Holidays from £1,891

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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.
Home2 Suites by Hilton Chicago River North

Home2 Suites by Hilton Chicago River North

3 out of 5
Downtown Chicago
Price was £2,915, price is now £1,891 per person
£1,891
per person
30 Mar - 3 Apr
found 9 hours ago
Return flight included
London (LON) to Chicago (ORD)
8.4/10 Very Good! (2,048 reviews)
Amazing hotel (clean and aesthetically pleasing), central to local hotspots and friendly staff! Would definitely recommend again.

Reviewed on 21 Feb 2026

Sentral Michigan Avenue

Sentral Michigan Avenue

4 out of 5
Downtown Chicago
Price was £2,985, price is now £1,928 per person
£1,928
per person
30 Mar - 3 Apr
found 9 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (983 reviews)
Habitación limpia, lugar agradable y tranqilo

Reviewed on 22 Feb 2026

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
Downtown Chicago
Price was £2,930, price is now £1,902 per person
£1,902
per person
30 Mar - 3 Apr
found 9 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (619 reviews)
The facility is all around good—upkeep, accommodations, robust heating during an extreme cold spell, plus responsive staff throughout, from entry desk to engineers to Greystar management office.

Reviewed on 6 Feb 2026

Kasa River North Chicago

Kasa River North Chicago

4 out of 5
Downtown Chicago
Price was £2,951, price is now £1,925 per person
£1,925
per person
30 Mar - 3 Apr
found 9 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (177 reviews)
Better furniture. Everything was very cheap quality

Reviewed on 22 Feb 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £2,952, price is now £1,932 per person
£1,932
per person
30 Mar - 3 Apr
found 9 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,229 reviews)
Everything was great!!!

Reviewed on 21 Feb 2026

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

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 £78 per night from 24 Feb to 25 Feb
£78
24 Feb - 25 Feb
includes taxes & fees
8/10 Very Good! (9,926 reviews)
Great place

Reviewed on 22 Feb 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £107 per night from 4 Mar to 5 Mar
£107
4 Mar - 5 Mar
includes taxes & fees
9.4/10 Exceptional! (3,390 reviews)
The room was spotless, all staff were friendly

Reviewed on 23 Feb 2026

Hotel Riu Plaza Chicago
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 £86 per night from 4 Mar to 5 Mar
£86
4 Mar - 5 Mar
includes taxes & fees
8.6/10 Excellent! (5,692 reviews)
Yes

Reviewed on 23 Feb 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,940 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 £1,891. 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

4.5/5(40 reviews)

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

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(14 reviews)

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 featuring a sunset and rides

Navy Pier

4/5(125 reviews)

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

Navy Pier

Things to do

Flyover in Chicago

Flyover in Chicago

£28
per adult
98% of travellers recommend
Flyover in Chicago
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
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.