Sleepy Hollow Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 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

    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.
  • Indoor wedding
    Aug 3 - Aug 8

    Swissotel - Chicago + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.0/10 - Wonderful (3,347 reviews)
    "The cleanest and nicest hotel in Chicago"
    Reviewed May 25, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £1,867
    £1,354
    per traveller
    found 16 hours ago
    Swissotel - Chicago
  • Smart TV
    Aug 2 - Aug 7

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.2/10 - Wonderful (488 reviews)
    "Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely."
    Reviewed May 22, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 2 stops ORD - LHR • 2 stops
    £1,950
    £1,374
    per traveller
    found 14 hours ago
    Level Chicago Fulton Market
  • Terrace/patio
    Jul 4 - Jul 11

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    7 nights
    5.0 star property
    9.6/10 - Exceptional (1,882 reviews)
    "Excellent"
    Reviewed May 21, 2026
    Return • Edinburgh (EDI) - Chicago (ORD)
    EDI - ORD • Direct ORD - EDI • Direct
    £3,153
    £2,358
    per traveller
    found 14 hours ago
    Trump International Hotel & Tower Chicago
  • Seasonal outdoor pool, pool loungers
    Aug 2 - Aug 7

    Viceroy Chicago + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (1,233 reviews)
    "I don’t think I have ever encountered a more polite, charming, and informed staff. As someone who has worked in the service industry I assume that your training program does an excellent job. The hotel is beautiful and well maintained. We’ll be back."
    Reviewed May 25, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 2 stops ORD - LHR • 2 stops
    £1,921
    £1,465
    per traveller
    found 14 hours ago
    Viceroy Chicago
  • Terrace/patio
    Jul 4 - Jul 11

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    7 nights
    4.0 star property
    9.4/10 - Exceptional (2,514 reviews)
    "The view from the corner room on the 7th floor of Pier 3 was absolutely superb—both the nightscape and the sunset were truly exceptional. I will definitely visit again."
    Reviewed May 26, 2026
    Return • Edinburgh (EDI) - Chicago (ORD)
    EDI - ORD • Direct ORD - EDI • Direct
    £2,350
    £1,801
    per traveller
    found 14 hours ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton

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 £118 per night from 27 May to 28 May
£118
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 £232 per night from 16 Jun to 17 Jun
£232
16 Jun - 17 Jun
includes taxes & fees
9.4/10 Exceptional! (4,248 reviews)
"This is an amazing hotel at this price. The complimentary buffet breakfast each morning is unbelievable. That alone is great, add to that great service. Gerardo at the front desk was great, got us checked in right away and always made sure to ask if there was anything we needed. The room was modern ..."

Reviewed on 25 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 £162 per night from 24 Jun to 25 Jun
£162
24 Jun - 25 Jun
includes taxes & fees
7.8/10 Good! (1,475 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.
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 . 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

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
Navy Pier

Navy Pier

4/5(127 reviews)

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

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

£16
per child
98% of travellers recommend
Flyover in Chicago
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.