Chicago is home to many icons: the Sears tower, two baseball teams with diehard fans, pizza that lives up to its deep dish name. Below, we’ve selected the top-things to do in Chicago whether you’re passing through or a local.
With so many sights, sightseeing shouldn’t just be left to the tourists. Book now and Save!
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What sightseeing tours are available in Chicago?
Chicago offers a variety of sightseeing experiences including architecture boat tours, helicopter tours, lakefront flight tours, segway city tours, and food & culture walking tours that highlight the city's top landmarks and history.
How long do Chicago sightseeing tours typically last?
Tour durations vary by experience — walking and boat tours usually last 1–2 hours, helicopter and flight tours range from 15–30 minutes, and combo experiences can last longer depending on the itinerary.
Do Chicago sightseeing tours operate year-round?
Most tours run year-round, but schedules can vary by season. Boat tours and outdoor experiences operate primarily in warmer months, while helicopter and flight tours run weather permitting throughout the year.
Where do Chicago sightseeing tours depart from?
Departure locations depend on the type of tour — boat tours typically depart from Navy Pier or the Chicago River, helicopter tours depart from Loop heliports, and flight tours leave from local airports like Chicago Executive or Midway.
Are sightseeing tours suitable for children and families?
Yes! Many tours are family-friendly. Age requirements vary by experience (particularly for flights and helicopter tours), so check individual tour details for minimum age or safety guidelines before booking.
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