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.
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.
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
Chicago: Navy Pier Centennial Wheel Ticket
Chicago Architecture Center River Cruise aboard First Lady
Top hotels in Sleepy Hollow
Embassy Suites by Hilton Chicago Downtown River North
First I made phone call day earlier before arriving Ruth answered the phone and her customer skills was absolutely amazing from there on it was great experience . To have to pay for early check in gets me upset because if check out early hotel does not reimburse me back
Reviewed on 11 Nov 2025
Hilton Chicago/Magnificent Mile Suites
Everything. Loved the experience.
Reviewed on 12 Nov 2025
citizenM Chicago Downtown
great hotel
Reviewed on 13 Nov 2025
Warwick Allerton - Chicago
Great
Reviewed on 12 Nov 2025
Hotel Riu Plaza Chicago
My stay at the Hotel Riu Plaza in downtown Chicago was absolutely incredible from start to finish! The location is perfect — right in the heart of the city, close to everything, yet quiet enough for a relaxing getaway. The highlight of my stay was the breakfast buffet. It was hands down one of the ...
Reviewed on 11 Nov 2025
The Whitehall Hotel, BW Premier Collection
Clean room, staff was friendly and very helpful, location was excellen, included buffet breakfast
Reviewed on 14 Nov 2025
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.
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.
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.
