Sleepy Hollow Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Sleepy Hollow Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
$775
per person
Oct 1 - Oct 5
found 18 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
$1,165
per person
Oct 1 - Oct 5
found 18 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
$1,244
per person
Oct 1 - Oct 5
found 18 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Everything
Reviewed on Aug 29, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
$1,055
per person
Oct 1 - Oct 5
found 18 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
This hotel truly exceeded my expectations and checked every box. From the moment we arrived, the property felt luxurious, stylish, and beautifully maintained. The accommodations were wonderful, and the attention to detail throughout the hotel really made the stay feel special.
The location was also excellent and made it convenient to enjoy everything the area had to offer. The rooftop was absolutely magnificent, the bar had a great atmosphere, and our room was spotless and refreshed every day.
What stood out most was the way the staff cared for their guests. Everyone was friendly, attentive, welcoming, and always willing to help. I did experience one minor issue during my stay, but it was handled quickly and professionally, which I truly appreciated.
Everything seemed to run like a well-oiled machine. Between the luxurious atmosphere, great location, beautiful rooftop, cleanliness, and outstanding service, this was an exceptional stay. I will definitely be returning!
Reviewed on Aug 28, 2026
Eurostars Magnificent Mile
Downtown Chicago
$898
per person
Oct 1 - Oct 5
found 18 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Excellent location and staff was friendly and very helpful. Elevators made funny noises though. Kinda scary. Still recommend.
Reviewed on Aug 28, 2026
Swissotel - Chicago
Downtown Chicago
$1,065
per person
Oct 1 - Oct 5
found 18 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
My sister and I came to Chicago from Baltimore to see the Obama Presidential Center. When I researched hotels to stay at in Chicago I was very impressed with Swissotel ratings. I could’ve made a better choice. We didn’t get to see everything we wanted to see, but when we do come back to Chicago Swissotel is definitely where we’ll be staying. So if you’re planning on coming to Chicago Swissotel is the best choice.
Reviewed on Aug 29, 2026
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See all available trips from Columbus to Sleepy Hollow
View all tripsSleepy Hollow Vacation Packages
Trying to save both time and money on your upcoming holiday to Sleepy Hollow? The AARP Travel Center Powered by Expedia® can help you do both. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Sleepy Hollow the best one yet. With only a few clicks, you can pick the best Sleepy Hollow vacation package for you. We have a fabulous choice of flights and hotels, and Sleepy Hollow endeavors to choose from.
Sleepy Hollow Hotels
Our listings include lodgings that are close to all the Sleepy Hollow points of interest, and some that are just outside the city center for a more restful retreat.
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Check out the verified hotel reviews on the AARP Travel Center to help you decide.
- It will be easy to choose a fabulous hotel, as a number of accommodations in Sleepy Hollow have a perfect overall rating of 5 stars
- You should have no issues taking it easy after a busy day, as these hotels have a perfect 5 star rating for room comfort.
- With a solid 3 rating, you know that you'll be greeted with a clean room when you return from exploring Sleepy Hollow
- The immaculate grounds of the area's hotels also got sky-high marks
Thanks to AARP Travel Center's Sleepy Hollow hotel packages, you not only get a great rate on your flight, but also a great place to stay.
Things to do in Sleepy Hollow
Sleepy Hollow is home to around 2,720,550 people, so you know there will be a lot to do no matter who you are. With this area's burgeoning art scene, local attractions, and a rich past that is a beacon for history buffs, you may have a hard time fitting everything into one trip. There are a large number of worthwhile things to do and see in and around Sleepy Hollow that can help make your trip a bit of an adventure. Not sure where to begin? Here are a several things that the area is known for:
- Grant Park and Buckingham Fountain
- Museum of Science and Industry
- Shedd Aquarium
- Chicago Architecture River Cruise
If you need more suggestions, then make sure to click on AARP's "Things to Do" tab.
Book Together and Save
As an AARP Member, you can take advantage of all the great deals. You'll save on select hotels worldwide, flights, and also car rentals. No matter what vacation package you pick, your membership savings helps you get a great deal. So what are you waiting for? Bundle now and get ready for your Sleepy Hollow vacation.
Top Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
River Hotel
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
Fairmont Chicago at Millennium Park
200 North Columbus Drive Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Hilton Chicago
720 S Michigan Ave Chicago IL
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
Holiday Inn Chicago Dwtn - The Mart by IHG
350 West Wolf Point Plaza, Building 2 Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our ...
L7 Chicago by LOTTE
225 N Wabash Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed, Oct 14 - Wed, Oct 21
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$148
Roundtrip
found 3 hours ago
Wed, Oct 14 - Wed, Oct 21
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$183
Roundtrip
found 3 hours ago
Thu, Oct 1 - Sun, Oct 4
LAX
Los Angeles Intl.
MDW
Midway Intl.
$197
Roundtrip
found 5 days ago
Tue, Sep 29 - Sat, Oct 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217
Roundtrip
found 3 hours ago
Tue, Sep 29 - Sat, Oct 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217
Roundtrip
found 3 hours ago
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