Sleepy Hollow, IL
Chicago
Visit Sleepy Hollow
Popular places to visit
Wrigley Field
Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.
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
With a visit to Navy Pier, a favorite shopping spot in Chicago, you can enjoy some retail therapy. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.
McCormick Place
During your trip, find out what's happening at McCormick Place, a top convention center in Chicago. Discover the acclaimed art scene and notable monuments in this vibrant area.
Soldier Field
Catch an event at Soldier Field during your trip to Chicago. Stroll along the lakeside or visit the notable monuments in this vibrant area.
Millennium Park
After visiting Millennium Park, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.
Sleepy Hollow Hotel Deals
Congress Plaza Hotel
Nice room and amazing view of lake Michigan. Very clean and staff was friendly. Only down side was our room was extremely hot.
Reviewed on 16 February 2026
Hotel Riu Plaza Chicago
The room was excellent
Reviewed on 16 February 2026
Hilton Chicago
All of the staff we talked to were extremely kind and helpful. We had something sent to the room twice. Both times the items arrived within 10 minutes. The room, which we paid $99 (after tax) to upgrade to, had a really great view of the lake, Navy Pier and Museum Campus. The room was updated. Even ...
Reviewed on 16 February 2026
Embassy Suites by Hilton Chicago Downtown River North
The clean rooms and the staff was excellent.
Reviewed on 16 February 2026
Hilton Chicago O'Hare Airport
Food at sports bar was great along with the service. Bedding was top notch, room clean& nice TV
Reviewed on 9 February 2026
Hilton Chicago/Magnificent Mile Suites
Very clean amazing staff and valet so convenient
Reviewed on 16 February 2026
Other neighborhoods 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 the city at Central Park Station (Pink Line) or Pulaski Station (Pink Line).
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.
