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.
Six Flags Great America
Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.
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.
Things to do
Skydeck - Willis Tower Admission
Wendella's 90-min Chicago River Architecture Tour
Chicago: Navy Pier Centennial Wheel Ticket
Sleepy Hollow Hotel Deals
Congress Plaza Hotel
"Our hvac unit in the room was one of the loudest I’ve ever had the displeasure of sleeping near. Had to turn it off to get sleep. Great views but definitely some historic wear that needs new paint in halls, elevator entries, etc. front doors were partially defunct our entire stay. No onsite parking ..."
Reviewed on May 26, 2026
Hotel Riu Plaza Chicago
"The hotel is clean and in a good location. The bathrooms are spacious and the showers were excellent. The rooms, however, are long, narrow, and cheaply furnished, with awkward closets and water-restricted faucets. The hotel feels designed to cut costs, without passing any savings to guests. Tile ..."
Reviewed on May 26, 2026
The Chicago Hotel Collection - Magnificent Mile
"El staff es un poco malhumorado Cuando tienes preguntas, la mayoria. Los tickets de comida o drinks gratis en realidad son descuentos, tienes q pagar. Excepto por el desayuno, solo use una vez cada uno, no me agrado, sali afuera. Regrese todos los demas tickets al hacer checkout. Gracias"
Reviewed on May 26, 2026
River Hotel
"Loved the reusable water bottles that are provided. The espressos throughout was a very nice touch. Will be back again in October for sure!"
Reviewed on May 26, 2026
Hotel Felix River North/Magnificent Mile
"Very understaffed and few amenities. Accommodating when we needed to change rooms though."
Reviewed on May 26, 2026
Freehand Chicago
"Good staff clean good people"
Reviewed on May 25, 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.
