Sleepy Hollow Travel Guide
Tourist Guide
Visit Sleepy Hollow
Popular places to visit
Wrigley Field
Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.
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 waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.
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.
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.
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.
Activities
Skydeck - Willis Tower Admission
Wendella's 90-min Chicago River Architecture Tour
Chicago Crime and Mob Bus Tour
Our pick of the best Sleepy Hollow Hotel Deals
Hilton Chicago/Magnificent Mile Suites
When I looked around the hotels near this one were several times more expensive…ie, The Four Seasons is very close by. While we know that’s a huge upgrade, the Hilton was clean, friendly and in a great location. We came back to sleep! The rooms are dated, but ours separated the king sized “bedroom” ...
Reviewed on 18 Apr 2026
Embassy Suites by Hilton Chicago Downtown River North
Clean and easy check in.
Reviewed on 17 Apr 2026
Congress Plaza Hotel
The hotel is opposite an above ground train and so there’s significant outdoor noise at night if you’re facing that side of the hotel.
Reviewed on 18 Apr 2026
Hotel Felix River North/Magnificent Mile
I found the price you pay for breakfast inclusion there would be more options then a danish, fruit, yogurt, and a coffee that there is a limitation on how much you get. The room was clean, there was issues with plumbing but they were working on fixing it. On the second floor the walls are thin I ...
Reviewed on 18 Apr 2026
Hotel Riu Plaza Chicago
A beautiful and comfortable hotel. Staff is professional and friendly. Breakfast buffet has endless choices.
Reviewed on 18 Apr 2026
Hilton Chicago O'Hare Airport
The room was spotless and the concierge service was excellent.
Reviewed on 17 Apr 2026
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.
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.
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.
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.
