Mix and match a stop from each category to create your own must-do lineup. The best part? Next time you visit, you can mix it again to create a whole new adventure.
The Ledge at Skydeck Chicago
The Ledge at Skydeck Chicago
| Credit: Courtesy of Choose Chicago

Your weekend in the Windy City will include an iconic Chicago experience, a unique food outing, a world-class museum, an architecture tour and a stop at Millennium Park. Ready to plan? Here's our mix-and-match itinerary:

Choose an Iconic Chicago Experience

Michigan Avenue/Oak Street shopping

Famed storefronts and unique boutiques line the shopper paradises of Michigan Avenue's Magnificent Mile and the Oak Street District.

Wrigley Field

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

Wabash Arts Corridor

Murals abound in this South Loop enclave, where public space is an urban canvas.

SkyDeck Chicago

Step out onto The Ledge at SkyDeck Chicago to see the city from 1,353 feet up.

Chicago beach
Chicago beach
| Credit: Courtesy of Illinois Office of Tourism


Play on the shores of Lake Michigan at one of the area's nearly two dozen public beaches.

Navy Pier

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

Lincoln Park Zoo

A free oasis of wildlife and green space sits among skyscrapers.


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

Lou Malnati's Pizza Chicago
Lou Malnati's Pizza
| Credit: Kevin J. Miyazaki/Redux

Pick a Unique Food Outing

Deep-dish pizza

The joke goes that it's not pizza unless it's thicker than the table. For tangy-sweet sauce, dive into the classic pie at a Lou Malnati's.

Chicago dog

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.

Celebrity chefs

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.

Food Emporium

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.

Field Museum
Field Museum
| Credit: Lucy Hewett/Field Museum

Visit a World-Class Museum

Field Museum

Peer up at Máximo, a titanosaur. He's not only the biggest dinosaur but the largest land animal—ever—on the planet. And he's just the first wonder to greet you at the Field Museum.

Museum of Science and Industry

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.

Shedd Aquarium

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

Adler Planetarium
Adler Planetarium

Adler Planetarium

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

Art Institute of Chicago

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

Chicago boat tour
Chicago boat tour
| Credit: Courtesy of Cruise Chicago

Go on an Architecture Tour

By boat

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.

By bus

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

By train

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

By foot

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

By exhibit

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

Take a Trip to Millennium Park

To mark the turn of the century, the city transformed a rail yard and sea of parking lots into a 25-acre gem. Completed in 2004, the park offers a quintessential city experience, making our must-list with its views, public art, gardens, performances and more.

Cloud Gate

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

BP Bridge

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

Lurie Garden, Millennium Park
Lurie Garden
| Credit: Alyssa Schukar

Lurie Garden

Stroll this sanctuary where plants rise taller than people.

Boeing Galleries

For a walk that is never the same twice, stroll through these outdoor galleries that house temporary modern art exhibitions, including large-scale sculptures.

Crown Fountain, Millennium Park
Crown Fountain
| Credit: Alyssa Schukar

Crown Fountain

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

Jay Pritzker Pavilion

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

McDonald's Cycle Center

Rent or store a bike at this facility built to encourage travel on two wheels.

See the City

It's the next best thing to having a friend take you around the city: a Chicago Greeter walking tour. No registration is needed for free one-hour InstaGreeter tours of downtown, Millennium Park, Uptown or Hyde Park. Or sign up 10 days in advance to be paired with a volunteer who'll tailor a sightseeing tour to your interests.