Experience the best of Chicago's arts, sports, and adventure in this action-packed 5-day itinerary for couples.

<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

Discover Chicago's iconic landmarks and cultural spots.

Chicago O'Hare International Airport

Millennium Park

Renowned art museum holding nearly 300,000 works from all over the world, spanning many centuries.

The Art Institute of Chicago

Cloud Gate

Embrace adventure and sports in Chicago.

Bike and Roll Chicago - Navy Pier

Lakefront Trail

Wrigley Field

Immerse in Chicago's vibrant arts and culture scene.

The Second City

Museum Of Contemporary Art Chicago

The Chicago Theatre

Savor Chicago's culinary delights and relax in its beautiful parks.

South Loop - Lou Malnati's Pizzeria

Grant Park

Navy Pier

Experience the rich history and architecture of Chicago.

Chicago History Museum

360 CHICAGO

Magnificent Mile

Explore the Vibrant Culture of Chicago in 5 Days

Bicycle

Adventure & Sports

Arts & Culture

Explore the Vibrant Culture of Chicago in 5 Days

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