Sleepy Hollow, IL
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.
Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
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.
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.
Six Flags Great America
Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.
Things to do
Wendella's 90-min Chicago River Architecture Tour
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
Sleepy Hollow Hotel Deals
Congress Plaza Hotel
"Complicated"
Reviewed on Jun 19, 2026
The Chicago Hotel Collection - Magnificent Mile
"Our stay was amazing! Staff was very helpful!"
Reviewed on Jun 19, 2026
Hyatt Regency O'Hare Chicago
"It’s our go-to place near the O’Hare Airport. Clean, safe, great amenities and friendly staff. I like the newly renovated rooms, too. No complaints!"
Reviewed on Jun 19, 2026
The Chicago Hotel Collection Ambassador Gold Coast
"Air conditioning not working"
Reviewed on Jun 19, 2026
Hilton Chicago/Magnificent Mile Suites
"Clean room exelent"
Reviewed on Jun 19, 2026
Hilton Chicago O'Hare Airport
"It was a great hotel for staying on site"
Reviewed on Jun 19, 2026
Where to stay in Sleepy Hollow
Downtown Chicago
Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
Magnificent Mile
Michigan Avenue and Chicago Water Tower are just a few worthwhile attractions to visit in Magnificent Mile. Travelers also love the fascinating museums, panoramic lake views, and popular shops.
The Loop
Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops, and acclaimed art galleries.
River North
Known for its fantastic nightlife, stunning river views, and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Oz Park, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.
Sleepy Hollow, IL
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