A Whirlwind Weekend in Chicago
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.
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
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 in Willis Tower to see the city from 1,353 feet up.
Beach Play on the shores of Lake Michigan.
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.
Theaters Improv comedy, Shakespeare, Broadway shows—the stage is set.
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.
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.
Popcorn Get the Garrett Mix, a combo of cheddar cheese with buttery caramel, at Garrett Popcorn Shops.
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.
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. In a special exhibit, Underwater Beauty, jellyfish pulse and eels change colors.
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.
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, 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 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 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. Free tours of Millennium Park leave twice a day. Or sign up 10 days in advance to be paired with a volunteer who’ll tailor a sightseeing tour to your interests, whether you’re into architecture, food, kid stuff, ethnic neighborhoods, LGBTQ-friendly stops or anything else. And just like with a friend, it’s all free.