Sleepy Hollow Travel Guide
Chicago
Visit Sleepy Hollow
Things to do
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
Top hotels in Sleepy Hollow
Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel
"The location was stellar. The room itself had long hairs all on the restroom but since we got in at 2am. I didnt have it in me to complain. The space is slightly outdated."
Reviewed on 16 Jul 2026
Hilton Chicago O'Hare Airport
"Very convenient for a quick overnight sleep and shower before connecting flight in the morning. Second time coming into Chicago from Miami at 11pm with connecting flight next day."
Reviewed on 17 Jul 2026
Congress Plaza Hotel
"When we made the reservation in April for July we requested a view, high floor, away from elevator and two extra pillows. We got floor 11 of 14 so pretty good. No view-looking across to other room, no extra pillows, elevator behind king room wall. A/c was horrible, 1st room of suite was 74 degree ..."
Reviewed on 17 Jul 2026
Hotel Riu Plaza Chicago
"what a great location, and the rooftop bar was sensational. Service was friendly and solid, breakfast was enough to last you till dinner, and the rooms (especially the showers) were great."
Reviewed on 17 Jul 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 Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.
