Sleepy Hollow, IL
Chicago
Visit Sleepy Hollow
Popular places to visit
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
McCormick Place
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Things to do
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Ticket
Chicago Sightseeing River and Lake Cruise
Wendella's Lake and River Architecture Tour
Chicago Architecture Center River Cruise aboard First Lady
Sleepy Hollow Hotel Deals
Congress Plaza Hotel
From the moment we walked in the security was very friendly and helpful the first front desk attendant was amazing her name was Jasmine she was incredibly sweet helped us the best she could when we came back to do an early check-in the second person who helped us was incredibly rude service was terrible ...
Reviewed on Oct 26, 2025
Holiday Inn Chicago Dwtn - The Mart by IHG
The room was very nice and clean. The bed was really comfortable. Staff was very helpful and the restaurant was excellent. Definitely would stay here again.
Reviewed on Oct 20, 2025
Hilton Chicago/Magnificent Mile Suites
Hotel was everything i needed for a work trip
Reviewed on Oct 25, 2025
Freehand Chicago
Everything was great
Reviewed on Oct 24, 2025
citizenM Chicago Downtown
Check in was easy and the room was comfortable and the breakfast was excellent
Reviewed on Oct 26, 2025
Embassy Suites by Hilton Chicago Downtown River North
Nice
Reviewed on Oct 24, 2025
Other neighborhoods around Sleepy Hollow
Near West Side
Live music, theaters, and shopping highlight some notable features of Near West Side. Make a stop by United Center or Credit Union 1 Arena while you're visiting, and jump aboard the metro at Racine Station or Polk Station (Pink Line) to get around town.
West Loop
Consider a visit to Milwaukee Avenue and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center.
South Loop
Known for its fascinating museums, panoramic lake views, and popular shops, there's plenty to explore in South Loop. Top attractions like Soldier Field and Lake Michigan are major draws. Catch the metro at Roosevelt Station or Cermak-McCormick Place Station to see more of the city.
Near South Side
Travelers choose Near South Side for its abundant dining options. Hop aboard the metro at Cermak-McCormick Place Station or Roosevelt Station and check out top sights like Soldier Field.
West Town
Noted for its live music and theaters, there's plenty to explore in West Town. Top attractions like The Salt Shed and Milwaukee Avenue are major draws, and you can hop on the metro at Division Station or Damen Station to see more of the city.
Wicker Park
Consider exploring the abundant dining options in Wicker Park. If sightseeing is on the list, Milwaukee Avenue is a top attraction. Hop on the metro at Damen Station or Division Station to see more of the area.
Sleepy Hollow, IL
- Wrigley Field
- Michigan Avenue
- Navy Pier
- Millennium Park
- Soldier Field
- Grant Park
- Chicago Riverwalk
- Lake Michigan
- United Center
- University of Chicago
- Northwestern University
- Donald E. Stephens Convention Center
- Willis Tower
- Merchandise Mart
- Loyola University Chicago
- Chicago Theatre
- State Street
- Allstate Arena
- Chicago Museum of Science and Industry
- Water Tower Place
- Rosemont Theatre
- University of Illinois Chicago
- Northwestern Memorial Hospital
- Lincoln Park Zoo
- 875 North Michigan Avenue
