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.
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.
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.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
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
Volo Auto Museum: Admission Ticket
Top hotels in Sleepy Hollow
Congress Plaza Hotel
The room was cold, temperature in room was about 63 degrees, front desk sent up maintenance engineer, temperature never got any warmer, had to sleep in our clothes with coats.
Reviewed on 2 Mar 2026
Hotel Riu Plaza Chicago
amazing staff and beautiful rooms and lobbies. i just loved the free breakfast
Reviewed on 1 Mar 2026
Embassy Suites by Hilton Chicago Downtown River North
Excellent, everything was perfect. We have no complaints. I will be booking again in April
Reviewed on 2 Mar 2026
Hilton Chicago/Magnificent Mile Suites
Everything was nice, only complaint was the water pressure in the shower was pretty terrible.
Reviewed on 2 Mar 2026
Eurostars Magnificent Mile
I really appreciated the staff who worked here. Furthermore, the view from my room was gorgeous.
Reviewed on 2 Mar 2026
Hilton Chicago
When we arrived we were put in not only incorrect rooms, but a room that was already occupied. Instead of upgrading us for the extremely uncomfortable experience of swiping into a room already occupied by another guest, they gave us a $10 credit. Not even enough to cover one of their water bottles. ...
Reviewed on 1 Mar 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 Old St Patrick’s Church 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.
