Sleepy Hollow
Chicago
Visit Sleepy Hollow
Popular places to visit
Wrigley Field
Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.
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.
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
A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.
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.
Millennium Park
One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour
Chicago Crime and Mob Bus Tour
Top hotels in Sleepy Hollow
Hilton Chicago/Magnificent Mile Suites
Great location. Very clean. Staff was helpful and very attentive. Our room was spacious and clean. Loved the in house food options. All the food we had there was amazing. Bar and bartender was awesome. Chris makes the BEST drinks. Pool area and gym on the top floor had spectacular views of the city ...
Reviewed on Apr 4, 2026
Congress Plaza Hotel
Stayed here several times. This is the only place I stay in Chicago and always a five star experience!
Reviewed on Apr 3, 2026
Embassy Suites by Hilton Chicago Downtown River North
It's a good hotel - but it can be very crowded. Expect long lines/waits for the elevator and breakfast. We were there end of March / beginning of April and the pool was so crowded we could not use it.
Reviewed on Apr 4, 2026
Hotel Riu Plaza Chicago
Comfortable Room
Reviewed on Apr 4, 2026
Hilton Chicago O'Hare Airport
I think you took advantage of people needing a place to stay when their flight was cancelled. The price was very inflated but we had very little choice about where we could stay.
Reviewed on Apr 4, 2026
The Wade
Clean room, great view, close to lake! Loved!
Reviewed on Apr 3, 2026
Other neighbourhoods 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 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
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.
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.
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.
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.
