3 Days in Chicago: Suggested Itineraries

Chicago is renowned for its stunning and original architecture, and the most relaxing way to see it is on a cruise on the Chicago River! You'll learn all ...  Read more

Location: Chicago, Illinois
Duration: 75-minutes

Gaze upon the city sights from the pinnacle of Chicago, the Skydeck. Located on the 103rd floor of Willis Tower, formerly Sears Tower -- the third-tallest ...  Read more

Location: Chicago, Illinois
Duration: Flexible

Get an exclusive view inside four famous Chicago pizzerias on this 3.5-hour tour and enjoy delicious slices at each! With your small group, go beyond the ...  Read more

Location: Chicago, Illinois
Duration: 3 hours 30 minutes (approx.)

See all the sights of Chicago at your own pace! On a Chicago City Hop-on Hop-off Tour you can get off the bus at any scheduled stop to visit Chicago's most ...  Read more

Location: Chicago, Illinois
Duration: Flexible

Experience all of Chicago’s best sights from the air on this exciting helicopter tour! Aboard a state-of-the-art helicopter, you'll enjoy a magnificent view of ...  Read more

Location: Chicago, Illinois
Duration: 30 minutes (approx.)

This comprehensive half-day tour of Chicago is the perfect introduction to the Windy City! Discover the highlights of Chicago’s North Side and South Side and ...  Read more

Location: Chicago, Illinois
Duration: 4 hours (approx.)

Discover Chicago's culinary side on this three-hour walking tour to taste the delicious flavors of the Gold Coast and Old Town. Along the way, your guide will ...  Read more

Location: Chicago, Illinois
Duration: 3 hours (approx.)

On this Chicago pizza-tasting tour with a friendly guide, visit four local pizzerias to try Chicago’s famous pizza and relax over cold beer or fine wine. ...  Read more

Location: Chicago, Illinois
Duration: 3.5 hours

Feel the need for speed? This exhilarating speedboat ride takes you out onto Lake Michigan for the ride of a lifetime. Experience the roar of the ...  Read more

Location: Chicago, Illinois
Duration: 30 minutes (approx.)

Don’t miss Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert ...  Read more

Location: Chicago, Illinois
Duration: Varies

Tour Chicago aboard a comfortable coach bus and enjoy a unique dining experience on this 3-hour progressive dining tour. Visit three Chicago restaurants for ...  Read more

Location: Chicago, Illinois
Duration: 3 hours (approx.)

Explore Chicago's international, modern and postmodern movements, from the powerful, minimalist work of Mies van der Rohe's to contemporary styles that ...  Read more

Location: Chicago, Illinois
Duration: 2 hours (approx.)

For fast, fun connections between some of Chicago’s top attractions, purchase a day pass for the city’s water taxi service. You can board the red, white and ...  Read more

Location: Chicago, Illinois
Duration: Varies

Follow the path of the Chicago blues music genre and the famous Blues Brothers on a luxury coach tour through the city. Hear interesting facts about how the ...  Read more

Location: Chicago, Illinois
Duration: 90 minutes (approx.)

Explore Chicago at your own pace on an independent bike tour. With your full-day bike rental, pedal along Lake Michigan and visit top Chicago attractions such ...  Read more

Location: Chicago, Illinois
Duration: Flexible

Accompanied by a local guide, take a city tour of Chicago and see its spectacular sights before ending the tour with a famous Chicago-style deep-dish pizza! ...  Read more

Location: Chicago, Illinois
Duration: 5 hours 30 minutes (approx.)

Experience the vitality and excitement of Chicago on this sightseeing tour! Explore Chicago's main business district, one of the financial epicenters of the ...  Read more

Location: Chicago, Illinois
Duration: 2 hours (approx.)

Get into the holiday spirit with this trolley tour in Chicago! See famous landmarks such as Lincoln Park, the Magnificent Mile and Daley Plaza, all beautifully ...  Read more

Location: Chicago, Illinois
Duration: 90 minutes (approx.)