Experience the best of family-friendly activities, delicious food, and natural wonders in Chicago, Windsor, and Toronto.

<p>The Windy City is an eclectic mix of modern art, buzz-worthy dining, cutting-edge comedy, and beloved sports teams. Snap a photo of your reflection in the silver Cloud Gate sculpture at Millennium Park before heading to Grant Park to get hit with the refreshing spray of Buckingham Fountain. There are dozens of museums and theater companies in Chicago, so a cultural experience is never hard to find. You’re sure to laugh to the point of tears at the Second City Theater, the launch pad of many famous comedians.</p>

Chicago, IL

Toronto

Windsor

Explore the vibrant city of Chicago.

Chicago O'Hare International Airport

Wrigley Field

Navy Pier

Discover the culinary delights of Chicago.

Portillo's & Barnelli's Chicago

Millennium Park

Magnificent Mile

Embark on an exciting adventure in Windsor.

Detroit Metropolitan Wayne County Airport

Adventure Bay Family Water Park Presented by WFCU Credit Union

Point Pelee National Park

Indulge in the flavors of Windsor.

The Twisted Apron

The Foundry Pub

Sand Point Beach

Experience the cosmopolitan charm of Toronto.

Landmark, over 553-metre tower featuring a glass floor & a revolving eatery with panoramic views.

CN Tower

Spacious market with 100+ vendors, bakers, butchers & artisans, with produce & antiques on weekends.

St. Lawrence Market

Sprawling natural history & world cultures galleries, plus dinosaur fossil skeletons.

Royal Ontario Museum

Enjoy nature and wildlife in Toronto.

Immense zoo with outdoor pavilions housing hundreds of species, plus a large botanical collection.

Toronto Zoo

Sprawling park with hiking trails, a zoo, sports fields & a large children's playground.

High Park

Islands across from mainland Toronto with various recreational activities, beaches & a theme park.

Family Fun in Chicago, Windsor, and Toronto

Download The Tripographer app!