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.
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
A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.
Millennium Park
One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.
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
Wendella's 90-min Chicago River Architecture Tour
Chicago Crime and Mob Bus Tour
Top hotels in Sleepy Hollow
Congress Plaza Hotel
Yes
Reviewed on 15 Mar, 2026
Hotel Riu Plaza Chicago
Great stay! No complaints! Breakfast buffet was a great plus!
Reviewed on 15 Mar, 2026
Embassy Suites by Hilton Chicago Downtown River North
Yes great
Reviewed on 15 Mar, 2026
Hilton Chicago/Magnificent Mile Suites
The Let out Couch Had really Bad Brown Stains in The Mattress We Left That Night!!!
Reviewed on 15 Mar, 2026
Hilton Chicago O'Hare Airport
Friendly check in and concierge. Had distilled water for CPAP. Clean room. Beds were not comfortable. Room very hot on arrival. Rooms need a refresh. Dated and worn. Shower water temperature variable (did not stay warm). I expected more from a Hilton, and at almost $400 a night.
Reviewed on 14 Mar, 2026
Hilton Chicago
Room was very clean. It’s disappointing that WiFi costs money unless you are a Hilton Honors member
Reviewed on 15 Mar, 2026
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 Polk Station (Pink Line) or Racine Station to get around town.
West Loop
Consider a visit to Old St Patrick’s Church 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.
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.
