Sleepy Hollow Travel Guide
Tourist Guide
Visit Sleepy Hollow
Popular places to visit
Wrigley Field
A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.
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.
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.
Navy Pier
One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Millennium Park
See mind-bending sculptures, a musically-inspired lawn and giant water fountains that double-up as video screens.
Activities
Chicago: Navy Pier Centennial Wheel Ticket
Chicago Crime and Mob Bus Tour
Skydeck - Willis Tower Admission
Our pick of the best Sleepy Hollow Hotel Deals
Congress Plaza Hotel
Yes perfectly clean
Reviewed on 24 Jan 2026
Embassy Suites by Hilton Chicago Downtown River North
Too few elevators working…
Reviewed on 28 Jan 2026
DoubleTree by Hilton Chicago - Magnificent Mile
Great
Reviewed on 27 Jan 2026
Hilton Chicago
Did not have breakfast
Reviewed on 19 Jan 2026
Hotel Riu Plaza Chicago
Perfect
Reviewed on 24 Jan 2026
Hilton Chicago O'Hare Airport
Great stay
Reviewed on 23 Jan 2026
Other neighbourhoods around Sleepy Hollow
Lawndale
When in Lawndale and the surrounding area, you'll want to check out sights like United Center or Garfield Park Conservatory and hop on the metro to see more of the city at Central Park Station (Pink Line) or Pulaski Station (Pink Line).
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 Polk Station (Pink Line) or Racine Station 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.
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.
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.
