Sleepy Hollow Travel Guide
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 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.
Things to do
360 CHICAGO Observation Deck
Chicago Sightseeing River and Lake Cruise
Chicago By Night River and Lake Cruise
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
Top hotels in Sleepy Hollow
Congress Plaza Hotel
"Nice room, hotel and housekeeping was great."
Reviewed on 21 Jun 2026
Hilton Chicago/Magnificent Mile Suites
"We stayed here for my daughter's birthday. The front desk staff was not the friendliest, they called us to let us know our room was ready when in fact it was not ready. We were already waiting in the lobby, so I went up to the front desk only to be told that actually our room was not ready. We waited ..."
Reviewed on 21 Jun 2026
The Chicago Hotel Collection - Magnificent Mile
"Very noisy in hall near elevator. Aggressive housekeeping (knocking on door repeatedly after saying no.) No “do not disturb” door hanger available. Room smelled of cigarettes. TV didn’t work."
Reviewed on 21 Jun 2026
Hyatt Regency O'Hare Chicago
"Property was really clean, restaurant was great especially one of the waiters (an older Hispanic gentleman). The check in lady was a bit rude and the staff from the Starbucks were super rude and not helpful. Stay was great and aside from that would stay again there."
Reviewed on 21 Jun 2026
The Chicago Hotel Collection Ambassador Gold Coast
"Beautiful lobby, clean rooms except the bathroom could’ve been cleaner. The only downside was the insulation kind of sucks, you can hear everything from other rooms. Other than that, amazing staff & quiet location."
Reviewed on 21 Jun 2026
Hilton Chicago O'Hare Airport
"Worn and tired room. Needs better deep cleaning and attention to chipped and damaged paint, bathroom surfaces, etc. I chose this hotel because of the free airport shuttle. Nowhere was it noted that I had to phone for pick-up. After waiting for more than 30 minutes, another hotel’s driver told me ..."
Reviewed on 21 Jun 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
Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.
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.
