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.

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

Wendella's 90-min Chicago River Architecture Tour

Chicago: Navy Pier Centennial Wheel Ticket

Chicago Blackhawks Ice Hockey Game at United Center

City Cruises Chicago: Lake Michigan Premier Dinner Cruise
Sleepy Hollow Hotel Deals

Hilton Chicago/Magnificent Mile Suites
Awesome
Reviewed on Dec 15, 2025

Silversmith Hotel Chicago Downtown
Awesome stay in an amazing room - lobby and bar/restaurant area were excellent as well. Location was perfect for our show at the CIBC Theatre nearby.
Reviewed on Dec 10, 2025

Club Quarters Hotel Wacker at Michigan, Chicago
Very clean and the staff was wonderful!
Reviewed on Dec 13, 2025

Palmer House a Hilton Hotel
The staff was so friendly and helpful and the hotel was beautiful
Reviewed on Dec 15, 2025

Embassy Suites by Hilton Chicago Downtown River North
Breakfast was delicious as always. But being in Chicago at this time of year, no AC was needed. LoL. Staff was exceptional! No complaints other than our room was directly in front of the elevator so it was a little loud on occasion 😔 but at the same time, it was convenient. ☺️
Reviewed on Dec 14, 2025

Eurostars Magnificent Mile
staff was very helpful & friendly, hotel was clean.
Reviewed on Dec 14, 2025
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.

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.

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.
Sleepy Hollow, IL
- Michigan Avenue
- Wrigley Field
- Navy Pier
- Soldier Field
- United Center
- Chicago Riverwalk
- Millennium Park
- Lake Michigan
- Grant Park
- University of Chicago
- Northwestern University
- Willis Tower
- State Street
- Donald E. Stephens Convention Center
- Chicago Theatre
- Loyola University Chicago
- Allstate Arena
- Griffin Museum of Science and Industry
- Water Tower Place
- 875 North Michigan Avenue
- Rosemont Theatre
- University of Illinois Chicago
- Merchandise Mart
- Lincoln Park Zoo
- House of Blues Chicago
- Chicago History Museum


