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.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
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.
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.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Sleepy Hollow Hotel Deals
Congress Plaza Hotel
"O"
Reviewed on May 18, 2026
Hotel Riu Plaza Chicago
"Excellent stay!!! Staff was very helpful and breakfast was delicious. We will stay here again!!!"
Reviewed on May 18, 2026
The Chicago Hotel Collection - Magnificent Mile
"Good location, definitely walkable to a lot of shops and restaurants."
Reviewed on May 18, 2026
Hotel Felix River North/Magnificent Mile
"Staff is excellent. Breakfast was below standards - muffins, fruit, juice, and a couple breakfast sandwiches the staff put in the microwave. I’d pass on the breakfast. Nice location. Rooms were okay - the bed in our room was full of cat scratches."
Reviewed on May 18, 2026
River Hotel
"My stay at the River Hotel was excellent from start to finish. The location is unbeatable, making it easy to explore the surrounding area, and the views were a great bonus. The room was clean, comfortable, and well-maintained, with everything I needed for a relaxing stay."
Reviewed on May 18, 2026
Freehand Chicago
"Rated 3 as We stayed at a 1 king bedroom on the 3rd floor for 3 nights. Room was a bit dusty and only provided 2 towels. Our shower gel was empty when we got to our room, good thing we had extra. We asked for refill 3 times but was never completed. Room was dark and didnt have a rug for the bathroom ..."
Reviewed on May 18, 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.
