Sleepy Hollow
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.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
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
Wendella's Lake and River Architecture Tour
Chicago: Navy Pier Centennial Wheel Ticket
Sleepy Hollow Hotel Deals
Hotel Felix River North/Magnificent Mile
loved my stay!
Reviewed on May 3, 2026
River Hotel
Staff was very friendly!
Reviewed on May 3, 2026
Hilton Chicago/Magnificent Mile Suites
There were blood stains on the carpet
Reviewed on May 3, 2026
Hotel Riu Plaza Chicago
I didn’t like the TV app, but everything else was perfect!
Reviewed on May 3, 2026
Club Quarters Hotel, Central Loop, Chicago
Billy in the front desk was kind and very helpful for my questions and needs
Reviewed on May 3, 2026
Hilton Chicago O'Hare Airport
Stayed there for the convenience, no amenities in the room, ac fan did not work and power cord to lamp and charging outlets next to bed did not work. Soundproof room did not stop us from hearing the elevator bell ding repeatedly from 5:00 am on
Reviewed on May 3, 2026
Other neighbourhoods 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.
