Explore the best of Chicago and Toronto with this romantic 5-day itinerary.

<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

Arrive in Chicago and explore iconic landmarks.

Millennium Park

The Art Institute of Chicago

Lou Malnati's Pizzeria

Discover more of Chicago's vibrant culture.

Shedd Aquarium

Field Museum

Chicago Riverwalk

Travel from Chicago to Toronto, relaxing in the city.

Chicago O'Hare International Airport

Toronto-area airport featuring lots of eateries & shops, free WiFi & rotating art displays.

Toronto Pearson International Airport

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

Royal Ontario Museum

Experience Toronto's lively neighborhoods and attractions.

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

St. Lawrence Market

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

CN Tower

Distillery District

Enjoy a relaxing day in Toronto before departure.

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

Toronto Islands

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

Memorable 5-Day Chicago to Toronto Adventure for Couples

Bookable Tours and Experiences - Chicago, IL

Bookable Tours and Experiences - Toronto

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