Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search over 1,000,000 properties worldwide and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any hotel reservation.


Sleepy Hollow Holiday Packages

Save Time and Money with Sleepy Hollow Holiday Packages

Thought about booking a Sleepy Hollow holiday package? It's really easy with Expedia, and you'll be able to buy a few fancy dinners or gifts for your friends back home with the cash you save.

If you secure a package deal on Expedia, you can save as much as $200*.

With more than 400 partner airlines and 750,000 properties worldwide for you to choose from on our international database, you'll be heading off on your holiday in no time!

Feel free to cancel or make changes to almost any hotel reservation and you won't pay any extra fees to us.

Places to Visit in Sleepy Hollow

Itinerary need filling up? Sleepy Hollow holiday all arranged but unsure what to expect when you get there? Let us make it easy for you.

Itching to go outside and have a little fun? The wider region has some wonderful activities for you to try, such as mountain biking. Still have time to spare? If you're eager for even more, grab the chance to go rock climbing as well.

Sleepy Hollow Accommodation

In terms of accommodation in central Sleepy Hollow, it doesn't pay to be choosy. However, there are as many as 24 properties in the surrounding areas. With Expedia, organising luxury getaways and cheap holidays is easy.

Like to know what our favourites are? Check out the Harvey House Bed & Breakfast (107 South Scoville Avenue) and the Bishops Hall (605 Iowa Street).

Nearest Airports to Sleepy Hollow

The instant that you exit the plane at Midway International Airport (MDW), you'll know your well-deserved trip to Sleepy Hollow has well and truly started! Well, the neighbourhood centre is still about 2 miles (3 km) away, but near enough.

*Savings based on all holiday package bookings with Flight + Hotel on Expedia.com from January through December 2017, as compared to price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.


Top Sleepy Hollow Hotel & Accommodation Deals

See all 1,603 properties in Sleepy Hollow
Hyatt Regency Chicago NZ$213
Reviewed on 6 Dec. 2019
See details
 
Hyatt Regency Chicago

Hyatt Regency Chicago

151 East Wacker Dr, Chicago, IL
     
    4.4 of 5
    4.0 out of 5.0 Stars

    Great location , clean property and friendly staff.

    Swissotel - Chicago NZ$170
    Reviewed on 7 Dec. 2019
    See details
     
    Swissotel - Chicago

    Swissotel - Chicago

    323 E Wacker Dr, Chicago, IL
       
      4.4 of 5
      4.5 out of 5.0 Stars

      This is a beautiful hotel and the rooms are amazing. Room service was quick and the food was really good

      Warwick Allerton - Chicago NZ$152
      Reviewed on 4 Dec. 2019
      See details
       
      Warwick Allerton - Chicago

      Warwick Allerton - Chicago

      701 North Michigan Avenue, Chicago, IL
         
        4.1 of 5
        4.0 out of 5.0 Stars

        Quietness and location were tops. Friendly and helpful staff.

        Radisson Blu Aqua Hotel Chicago NZ$226
        Reviewed on 7 Dec. 2019
        See details
         
        Radisson Blu Aqua Hotel Chicago

        Radisson Blu Aqua Hotel Chicago

        221 N Columbus Dr, Chicago, IL
           
          4.5 of 5
          4.5 out of 5.0 Stars

          Nicely updated room.. clean and comfortable. Nice staff. Would stay here again

          Hilton Chicago- Michigan Ave Cultural Mile NZ$170
          Reviewed on 7 Dec. 2019
          See details
           
          Hilton Chicago- Michigan Ave Cultural Mile

          Hilton Chicago- Michigan Ave Cultural Mile

          720 S Michigan Ave, Chicago, IL
             
            4.2 of 5
            4.0 out of 5.0 Stars

            Convenient to downtown Chicago. Beautiful building.

            La Quinta Inn & Suites by Wyndham Chicago Downtown NZ$150
            Reviewed on 1 Dec. 2019
            See details
             
            La Quinta Inn & Suites by Wyndham Chicago Downtown

            La Quinta Inn & Suites by Wyndham Chicago Downtown

            1 S Franklin Street, Chicago, IL
               
              4.5 of 5
              3.0 out of 5.0 Stars

              The staff was very helpful in directing us to our locations. Breakfast choices were amazing

              Hilton Chicago O'Hare Airport NZ$185
              Reviewed on 2 Dec. 2019
              See details
               
              Hilton Chicago O'Hare Airport

              Hilton Chicago O'Hare Airport

              Ohare International Airport, Chicago, IL
                 
                3.9 of 5
                4.0 out of 5.0 Stars

                We use this hotel to stay the night before our early AM flight. Excellent! We only needed to walk and we are at the gate literally.

                Eurostars Magnificent Mile, previously Dana Hotel NZ$169
                Reviewed on 7 Dec. 2019
                See details
                 
                Eurostars Magnificent Mile, previously Dana Hotel

                Eurostars Magnificent Mile, previously Dana Hotel

                660 North State Street, Chicago, IL
                   
                  4.4 of 5
                  4.0 out of 5.0 Stars

                  This was a five star hotel at a three star price. I highly recommend it.

                  Sleepy Hollow Flight Deals

                  These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.