Sleepy Hollow Travel Guide
Tourist Guide
Visit Sleepy Hollow
Popular places to visit
Wrigley Field
A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.
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.
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
One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.
Millennium Park
See mind-bending sculptures, a musically-inspired lawn and giant water fountains that double-up as video screens.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
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
Congress Plaza Hotel
Do not stay here. There was no hotel, you cannot control the temperature of the ac and it was gross. Stayed in room 404.
Reviewed on 15 Mar 2026
Hotel Riu Plaza Chicago
The room was so clean, the staff were very kind and polite, helpful and made the hotel very welcoming!! The area was also safe and had lots of shopping areas and restaurants! 10/10 would recommend for everyone! Made my friend’s birthday wonderful! Thank you RIU!
Reviewed on 15 Mar 2026
Embassy Suites by Hilton Chicago Downtown River North
Just a little loud.
Reviewed on 15 Mar 2026
Hilton Chicago/Magnificent Mile Suites
We stayed at Hilton because of the amazing reviews, however we did not experience the magic, we stayed one night and had intentions of staying for the weekend, however it was cut short, walls were very thin, we could hear toilets flushing, doors closing from our neighbors. We were right next to young ...
Reviewed on 14 Mar 2026
Hilton Chicago O'Hare Airport
Friendly check in and concierge. Had distilled water for CPAP. Clean room. Beds were not comfortable. Room very hot on arrival. Rooms need a refresh. Dated and worn. Shower water temperature variable (did not stay warm). I expected more from a Hilton, and at almost $400 a night.
Reviewed on 14 Mar 2026
Eurostars Magnificent Mile
Friendly staff
Reviewed on 12 Mar 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 Old St Patrick’s Church 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.
