Sleepy Hollow Travel Guide
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 find the perfect gifts to bring home 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 Sightseeing River and Lake Cruise
Wendella's Lake and River Architecture Tour
Top hotels in Sleepy Hollow
Congress Plaza Hotel
Reviewed on 20 Oct 2025
Hilton Chicago/Magnificent Mile Suites
Reviewed on 20 Oct 2025
Freehand Chicago
Reviewed on 19 Oct 2025
citizenM Chicago Downtown
Reviewed on 18 Oct 2025
Embassy Suites by Hilton Chicago Downtown River North
Reviewed on 20 Oct 2025
The Allegro Royal Sonesta Hotel Chicago Loop
Reviewed on 20 Oct 2025
Other neighbourhoods around Sleepy Hollow
Near West Side
Live music, theatres 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
Soldier Field and Lake Michigan are a few top attractions in South Loop. Hop around the city on the metro at Roosevelt Station or Cermak-McCormick Place Station and check out the area's fascinating museums, panoramic lake views and popular shops.
Near South Side
Travellers choose Near South Side for its ample 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 theatres, 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
Spend some time visiting places like Milwaukee Avenue while getting to know Wicker Park, and be sure to check out the abundant dining options. You can hop aboard the metro at Damen Station or Division Station to see more of the area.
Sleepy Hollow Travel Guide
- Wrigley Field
- Navy Pier
- Millennium Park
- Grant Park
- Chicago Riverwalk
- Lake Michigan
- Northwestern University
- Art Institute of Chicago
- Willis Tower
- Chicago Theatre
- Allstate Arena
- Chicago Museum of Science and Industry
- Field Museum of Natural History
- Water Tower Place
- University of Illinois Chicago
- Northwestern Memorial Hospital
- Lincoln Park Zoo
- 875 North Michigan Avenue
- Cloud Gate
