Sleepy Hollow Holidays from £1,187

Book a Hotel + Flight or Car together to unlock savings

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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,767, price is now £1,187 per person
£1,187
per person
29 Sept - 6 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
We stayed for our first time in Chicago. Loved the area. The hotel is clean and well maintained. The staff is amazing. Thank you, Marena for welcoming us.

Reviewed on 14 Jul 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,319, price is now £1,446 per person
£1,446
per person
29 Sept - 6 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We booked a two bedroom unit, but the unit clearly wasn't intended for a 2 bedroom. It was obviously a sitting area or something with a bed squeezed in. There was no vent so it made it impossible to shut the door, but then it was open to the living space and a full wall of windows. In addition, they list housekeeping as an amenity, and advertise one day or long term stays, however, for our 4 night stay, this didn't get housekeeping services. Meaning we had to get towels and coffee each day from the front desk, had piles of trash from cooking and such, and a heap of dirty towels from the week. Staff was friendly, but not really provided agency or capacity to do anything to fix the experience. Even a request for a fan to try to cool the space was impossible for them to solve (although they certainly had one for the front desk to keep staff comfortable).

Reviewed on 14 Jul 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,851, price is now £1,949 per person
£1,949
per person
29 Sept - 6 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
We loved our "upgraded" room with the beautiful view of the river, Lake Michigan and the Saturday night fireworks! This was thanks to Michael, our concierge or check-in man at the front desk. It took us a little while to figure out all the lighting but that was a small thing. The coffee at your restaurant left a little to be desired - it was not hearty enough or warm enough. The cappuccino we replaced it with was very good! All in all, a very happy experience.

Reviewed on 14 Jul 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was £1,892, price is now £1,310 per person
£1,310
per person
29 Sept - 6 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
We would absolutely stay here again and highly recommend the Omni to anyone visiting Chicago.

Reviewed on 14 Jul 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 £1,905, price is now £1,346 per person
£1,346
per person
29 Sept - 6 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Very clean nice workers and amazing views

Reviewed on 14 Jul 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
A busy city street with tall buildings, a bus, and cars.

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

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is £144 per night from 3 Aug to 4 Aug
£144
3 Aug - 4 Aug
includes taxes & fees
8.8/10 Excellent! (2,845 reviews)
"This is the third time we’ve stayed, and every time we’ve enjoyed, property is well kept, nice rooms, great staff, wonderful breakfast, would definitely recommend!"

Reviewed on 14 Jul 2026

Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is £146 per night from 27 Jul to 28 Jul
£146
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very good! (1,748 reviews)
"We decided to extend our stay and the staff were amazing. Very courteous !!!"

Reviewed on 13 Jul 2026

The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is £234 per night from 26 Jul to 27 Jul
£234
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (1,909 reviews)
"We would absolutely stay here again and highly recommend the Omni to anyone visiting Chicago."

Reviewed on 14 Jul 2026

Omni Chicago Hotel
See all 4,596 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 £1,187. 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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£19
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Flyover in Chicago

Flyover in Chicago

£24
per adult
96% 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.