Sleepy Hollow, IL
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.
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.
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.
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 ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Things to do
Skydeck - Willis Tower Admission
Wendella's 90-min Chicago River Architecture Tour
Sleepy Hollow Hotel Deals
Congress Plaza Hotel
"Bath tub didn’t drain, elevator/s didn’t work, we could hear the people next door like there weren’t even walls in between us."
Reviewed on May 31, 2026
Hotel Riu Plaza Chicago
"Great location, nice room, great buffet breakfast with very attentive and friendly staff."
Reviewed on May 31, 2026
The Chicago Hotel Collection - Magnificent Mile
"Great location for shopping. Well maintained, slightly dated rooms."
Reviewed on May 31, 2026
Fairmont Chicago at Millennium Park
"We had reserved a king bed, but since we checked in later in the evening, I guess none were available and my wife and I ended up with twin beds instead. Overall, our experience with the front desk staff was mixed — some were very friendly and helpful, while others were not."
Reviewed on May 30, 2026
The Chicago Hotel Collection Ambassador Gold Coast
"Great location!!!"
Reviewed on May 31, 2026
Freehand Chicago
"Overall, we had a good stay at the Freehand Chicago. The location was convenient, and despite being in a busy area, we slept peacefully throughout the night. The hotel was also accommodating in holding our luggage after checkout since we had a later flight, which we appreciated. That said, there ..."
Reviewed on May 30, 2026
Other neighborhoods 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.
