Sleepy Hollow Travel Guide
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 find the perfect gifts to bring home 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
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
Top hotels in Sleepy Hollow
Congress Plaza Hotel
"Room floor was filthy Air conditioning didn’t work in the room. The only good thing was the pillows and the view of Grant Park."
Reviewed on 27 May 2026
Hotel Riu Plaza Chicago
"Staff was super friendly. Rooftop bar is awesome. The breakfast was fantastic. This may sound weird, but the toilet seats had abnormally large openings."
Reviewed on 27 May 2026
The Chicago Hotel Collection - Magnificent Mile
"Just parking"
Reviewed on 27 May 2026
River Hotel
"had an excellent stay.... very nice hotel for the price. Great location. Great room."
Reviewed on 27 May 2026
Hotel Felix River North/Magnificent Mile
"Staff was wonderful. Would’ve stayed an extra night if we didn’t need to go back to work."
Reviewed on 27 May 2026
Freehand Chicago
"The Hotel is in bad need of a update & remodel. Rooms are very small and dark and Dingy. carpet is very warn. We went to the room we were given an there was some kind of very loud running contently outside the window had to go to the front desk and ask for a new room. The next room was on the same ..."
Reviewed on 27 May 2026
Other neighbourhoods around Sleepy Hollow
Near West Side
Live music, theatres 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
Soldier Field and Lake Michigan are a few top attractions in South Loop. Hop around the city on the metro at Roosevelt Station or Cermak-McCormick Place Station and check out the area's fascinating museums, panoramic lake views and popular shops.
West Town
Noted for its live music and theatres, 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
Travellers choose Near South Side for its ample dining options. Hop aboard the metro at Cermak-McCormick Place Station or Roosevelt Station and check out top sights like Soldier Field.
Wicker Park
Spend some time visiting places like Milwaukee Avenue while getting to know Wicker Park, and be sure to check out the abundant dining options. You can hop aboard the metro at Damen Station or Division Station to see more of the area.
