Sleepy Hollow, IL
Chicago
Visit Sleepy Hollow
Popular places to visit
Wrigley Field
Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.
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.
McCormick Place
During your trip, find out what's happening at McCormick Place, a top convention center in Chicago. Discover the acclaimed art scene and notable monuments in this vibrant area.
Navy Pier
With a visit to Navy Pier, a favorite shopping spot in Chicago, you can enjoy some retail therapy. Amble around this vibrant area's lakeside or experience its fascinating museums.
Six Flags Great America
Enjoy the excitement at Six Flags Great America and see why people love this theme park in Gurnee. Stroll along the lakeside or visit the shops in this family-friendly area.
Millennium Park
After visiting Millennium Park, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.
Sleepy Hollow Hotel Deals
Embassy Suites by Hilton Chicago Downtown River North
Clean room; kind and courteous staff; excellent breakfast and happy hour included
Reviewed on 10 November 2025
Hilton Chicago/Magnificent Mile Suites
Restaurant was good, room nice
Reviewed on 11 November 2025
Congress Plaza Hotel
It was fine in general. Location was great but view was not perfect just fine
Reviewed on 9 November 2025
citizenM Chicago Downtown
Yes 10/10 definitely will be back soon
Reviewed on 11 November 2025
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Friendly staff, very comfortable room
Reviewed on 11 November 2025
Freehand Chicago
This is the perfect place to stay. The Red Line station is 1 1/2 blocks away and is the key to public transportation in Chicago.
Reviewed on 4 November 2025
Other neighborhoods 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, 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
- Places of interest
- Sleepy Hollow Hotels by Star Rating
- Hotels in top Chicago neighborhoods
- Sleepy Hollow Hotels by Brand
- Wrigley Field
- Michigan Avenue
- McCormick Place
- Millennium Park
- Navy Pier
- Grant Park
- Lake Michigan
- Soldier Field
- Chicago Riverwalk
- United Center
- University of Chicago
- Northwestern University
- Donald E. Stephens Convention Center
- Art Institute of Chicago
- Willis Tower
- Merchandise Mart
- Loyola University Chicago
- Chicago Theatre
- State Street
- Field Museum of Natural History
- Water Tower Place
- Wintrust Arena
- Rate Field
- Allstate Arena
- Griffin Museum of Science and Industry
- Rosemont Theatre
- SeatGeek Stadium
- Lincoln Park Zoo
- 875 North Michigan Avenue
- Cloud Gate
- Northwestern Memorial Hospital
- University of Illinois Chicago
