Chicago Vacation Activities

See for yourself why Chicago was voted the #1 bike-friendly city in the United States by Bicycling Magazine. Explore over 120 miles of bikeways, including the magnificent lakefront.

Journey to the moon, the stars, the edge of the galaxy, and beyond … all without leaving Chicago. The Adler Planetarium has been delighting star-struck audiences for more than 70 years!

Departing from Navy Pier, this 75-minute architectural tour features exciting views of Chicago's most famous architecture as seen from the Chicago River and lakefront.

Turn the Windy City into the shopping city! Explore boutiques in two of Chicago’s hippest neighborhoods—Bucktown and Wickerpark. Your shopping guide leads the way, keeping your hands free of maps so you can carry more bags!

Hop on a bike for an excursion into the art, history, and nature of Chicago’s lakefront. Your tour guide will take you to some of Chicago’s best known sites, including Lincoln, Millennium, and Grant Parks.

Make your day special as you indulge your senses with stunning views of Chicago, a delectable brunch buffet, and live entertainment.

CityPass is the ticket to the Windy City's most popular attractions—including the Shedd Aquarium, Sears Tower Skydeck, Adler Planetarium, and Museum of Science & Industry—at up to 45% savings. With a leisurely nine days to use the tickets and line-skipping privileges, it's perfect for a weekend or a week! Buy now and save 47%—and skip standing in lines!

Break away from the typical tourist locations! As you explore neighborhoods from Gold Coast and Old Town to Lincoln Park and Lakeview, you’ll experience this culturally rich and diverse city as a true Chicagoan does.