Sleepy Hollow, IL
Chicago
Visit Sleepy Hollow
Popular places to visit
Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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
Chicago Bulls Basketball Game at United Center
Chicago: Navy Pier Centennial Wheel Ticket
Chicago Blackhawks Ice Hockey Game at United Center
Chicago Museum of Contemporary Art: General Admission Ticket
Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting
Sleepy Hollow Hotel Deals
Congress Plaza Hotel
Room was clean. Only interaction i had with staff is when i checked in and checked out. You should add on your advertisement, parking that you pay 62 a day for has no in and out privileges. No one rents a car to leave parked. How many times a day do i have to keep paying 62? I gave it a food rating ...
Reviewed on Jan 20, 2026
Hilton Chicago
Did not have breakfast
Reviewed on Jan 19, 2026
The Royal Sonesta Chicago Downtown
GREAT HOTEL
Reviewed on Jan 22, 2026
River Hotel
Good
Reviewed on Jan 23, 2026
DoubleTree by Hilton Chicago - Magnificent Mile
Service was nice. Dinner was good. Breakfast leave a little to be desired though.
Reviewed on Jan 21, 2026
Hilton Chicago/Magnificent Mile Suites
Great stay
Reviewed on Jan 24, 2026
Other neighborhoods around Sleepy Hollow
Lawndale
When in Lawndale and the surrounding area, you'll want to check out sights like United Center or Garfield Park Conservatory and hop on the metro to see more the city at Central Park Station (Pink Line) or Pulaski Station (Pink Line).
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.
Sleepy Hollow, IL
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