Sleepy Hollow Vacations
Book a Hotel + Flight or Car together to unlock savings
Your Sleepy Hollow Vacation
Experience everything this neighborhood has to offer with a tailor-made Sleepy Hollow vacation package. However you picture yourself spending your time here, you'll find endless opportunities for fun, relaxation and adventure. What to cross off your itinerary first? Nearby Balzekas Museum of Lithuanian Culture is one thing you can't miss during your trip to Sleepy Hollow. Expedia will help turn your dream Sleepy Hollow vacation into reality, whatever your travel plans or budget.
- Hollywood Casino Aurora
Jul 27 - Jul 30Hollywood Casino Aurora + Flight
Aurora3 nightsRoundtrip • Atlanta (ATL) - Chicago (MDW)ATL - MDW • Nonstop MDW - ATL • Nonstop$1,531$392found 2 days agoper traveler - Level Chicago Fulton Market
Aug 21 - Aug 25Level Chicago Fulton Market + Flight
Downtown Chicago4 nights9.2/10 - Wonderful (493 reviews)"Fully equipmet"Reviewed June 2, 2026Roundtrip • Atlanta (ATL) - Chicago (MDW)ATL - MDW • Nonstop ORD - ATL • Nonstop - Level Chicago – Old Town
Aug 21 - Aug 25Level Chicago – Old Town + Flight
Downtown Chicago4 nights9.0/10 - Wonderful (488 reviews)"Very clean and loved the location and amenities with the store on the first floor was fantastic"Reviewed June 3, 2026Roundtrip • Atlanta (ATL) - Chicago (MDW)ATL - MDW • Nonstop ORD - ATL • Nonstop - JW Marriott Chicago
Aug 27 - Aug 29JW Marriott Chicago + Flight
Downtown Chicago2 nights9.2/10 - Wonderful (1,001 reviews)"Good customer service and the food in the lobby restaurants was so good! Also the service at that restaurant is amazing I believe her name was Stephanie, she went out of her way to find me caffeine free Diet Coke. Also, we forgot to tell them that we don’t eat bacon after the hamburger came. They happily to get back and started another hamburger to make sure there’s no bacon residue in it."Reviewed May 31, 2026Roundtrip • Atlanta (ATL) - Chicago (MDW)ATL - MDW • Nonstop MDW - ATL • Nonstop - The Royal Sonesta Chicago River North
Jul 9 - Jul 13The Royal Sonesta Chicago River North + Flight
Downtown Chicago4 nights9.2/10 - Wonderful (2,624 reviews)"Great location, friendly staff"Reviewed June 1, 2026Roundtrip • Atlanta (ATL) - Chicago (MDW)ATL - MDW • Nonstop MDW - ATL • Nonstop
Where to stay in Sleepy Hollow
Downtown Chicago
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Sleepy Hollow Hotel Deals
Congress Plaza Hotel
"Well located yet aged facility. Bathrooms are small and frankly nasty. It served our purpose as a base for a 3-day stay in Chicago with errands to run in the nearby area."
Reviewed on Jun 4, 2026
The Chicago Hotel Collection - Magnificent Mile
"Clean room"
Reviewed on Jun 3, 2026
Hotel Riu Plaza Chicago
"It is a great place to stay. The breakfast was good. However, you don’t get toothpaste and some other bathroom amenities which is something they can improve."
Reviewed on Jun 4, 2026
Discover the most popular places to visit in Sleepy Hollow
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Wendella's 90-min Chicago River Architecture Tour
