A Whirlwind Weekend in the Windy City

Famed storefronts and unique boutiques line this shopper’s paradise.

Catch a Cubs game and snap a pic with the famed marquee.

With stunning views and a children’s museum, the city’s playground juts into Lake Michigan.

Improv comedy, Shakespeare, Broadway shows—the stage is set.

Step out onto The Ledge in Willis Tower to see the city from 1,353 feet up.

The joke goes that it’s not pizza unless it’s thicker than the table. Dive into a classic pie at Gino’s East.

This delicacy comes loaded with trimmings, including peppers, tomato and a pickle, but never, ever ketchup. For an authentic experience, try the Jumbo Hot Dog at a Portillo’s restaurant.

Sample the scene and the grilled pork belly at Stephanie Izard’s Girl and the Goat, or ceviche and anything with mole at Rick Bayless’ Frontera Grill. 

Eataly Chicago, a two-story market and high-end food court, celebrates Italian and Mediterranean cuisine. Swing by to taste Sicilian cannoli or see burrata made.

Get the Garrett Mix, a combo of cheddar cheese with buttery caramel, at Garrett Popcorn Shops.

Peer up at Máximo, a titanosaur. He’s not only the biggest dinosaur but the largest land animal—ever—on the planet.

Tap into your inner explorer at the Western Hemisphere’s largest science museum, complete with a tour of the German U-505 submarine captured during WWII.

See more than 32,000 animals from the Great Lakes to the deepest reaches of the Amazon. In a special exhibit, Underwater Beauty, jellyfish pulse and eels change colors.

Cast your eyes to the sky and view celestial objects trillions of miles away at the Adler’s Doane Observatory.

Immerse yourself in art from ancient days to today at the Art Institute, where a pair of bronze lions famously flank the entryway.

Join the volunteer docents of the Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady to learn the history behind the city’s famous skyline.

Catch a lift with the knowledgeable guides of a hop-on, hop-off, double-decker bus tour to hit the city’s downtown attractions at your own pace.

All aboard the elevated train—or the L, as locals call it—for a top-down perspective on 
the city’s must-see sights, courtesy of Chicago Architecture Center guides.

Chicago is known for groundbreaking architecture and trendsetting neighborhoods. To see both in one trip, tour with an expert from Inside Chicago Walking Tours. 

Visit the Chicago Architecture Center above the Riverwalk to explore a model of the city and visit a skyscraper gallery.

Gaze at your reflection—and the skyline’s—in this 110-ton seamless steel sculpture affectionately dubbed The Bean.

Wind along a ribbon-like path framed in glittering stainless-steel panels to earn a full view of Millennium Park.

Stroll this sanctuary where plants rise taller than people.

Splash in the reflective pool between two 50-foot glass towers that project the diverse faces of Chicago’s citizens.

Take in a concert or film beneath a trellis of stainless-steel beams designed for both acoustics and aesthetics.