Explore thrilling adventures and serene beaches in this 7-day journey from Chicago to Playa del Carmen.

<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

Playa del Carmen, Quintana Roo, Mexico

<p>Experience New York City, the ultimate urban adventure. Explore iconic landmarks, diverse neighborhoods, world-class dining, and unforgettable cultural experiences in the city that never sleeps.</p>

New York City

Texas City

Arrive in Chicago and explore the city’s iconic landmarks.

Millennium Park

The Art Institute of Chicago

Iconic, 110-story skyscraper featuring expansive views of Chicago from its 103rd-story Skydeck.

Willis Tower

Experience the vibrant nightlife and dining in Chicago.

Lou Malnati's Pizzeria

Chicago Riverwalk

The Aviary

Fly from Chicago to New York City for a day of exploration.

Iconic National Monument opened in 1886, offering guided tours & a museum, plus harbor & city views.

Statue of Liberty National Monument

Sprawling park with pedestrian paths & ballfields, plus a zoo, carousel, boat rentals & a reservoir.

Central Park

A grand setting for one of the world's greatest collections of art, from ancient to contemporary.

The Metropolitan Museum of Art

Discover more cultural gems in New York City.

Iconic, art deco office tower from 1931 with exhibits & observatories on the 86th & 102nd floors.

Empire State Building

Bustling destination in the heart of the Theater District known for bright lights, shopping & shows.

Times Square

Popular park 30 feet above street level on an old rail line, with river & city views.

7-Day Adventure and Leisure Trip: Chicago to Playa del Carmen

Bookable Tours and Experiences - Chicago, IL

Bookable Tours and Experiences - Playa del Carmen, Quintana Roo, Mexico

Bookable Tours and Experiences - New York City

Need a hotel or flight? Search below:

Download The Tripographer app!