Sleepy Hollow Travel Guide
Tourist Guide
Visit Sleepy Hollow
Popular places to visit
Wrigley Field
A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.
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
One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.
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
See mind-bending sculptures, a musically-inspired lawn and giant water fountains that double-up as video screens.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Activities
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Ticket
Chicago Architecture Center River Cruise aboard First Lady
Wendella's 90-min Chicago River Architecture Tour
Chicago Crime and Mob Bus Tour
Our pick of the best Sleepy Hollow Hotel Deals
Embassy Suites by Hilton Chicago Downtown River North
It was fine
Reviewed on 5 Nov 2025
Congress Plaza Hotel
Yes
Reviewed on 3 Nov 2025
Hilton Chicago/Magnificent Mile Suites
Great staff at the front desk!
Reviewed on 2 Nov 2025
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Easy to get around. Lively area and no need for a car to get around.
Reviewed on 1 Nov 2025
citizenM Chicago Downtown
Receptionist made the stay 100x better
Reviewed on 4 Nov 2025
Freehand Chicago
Staff interactions were excellent in every aspect.
Reviewed on 2 Nov 2025
Other neighbourhoods around Sleepy Hollow
Little Village
Be sure to check out the bars and art galleries while you're strolling through Little Village, and hop on the metro at California Station (Pink Line) to see more of the surrounding area.
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.
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.
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.
Sleepy Hollow Travel Guide
- Wrigley Field
- Navy Pier
- McCormick Place
- Millennium Park
- Grant Park
- Lake Michigan
- Northwestern University
- Art Institute of Chicago
- Willis Tower
- Merchandise Mart
- Allstate Arena
- Field Museum of Natural History
- Water Tower Place
- Wintrust Arena
- SeatGeek Stadium
- Lincoln Park Zoo
- 875 North Michigan Avenue
- Cloud Gate
