A Whirlwind Weekend in 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
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.
Step out onto The Ledge at SkyDeck Chicago to see the city from 1,353 feet up.
Play on the shores of Lake Michigan at one of the area's nearly two dozen public beaches.
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.
Related: 36 Hours in Chicago
Pick a Unique Food Outing
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.
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.
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.
Related: Top Things to Do in Chicago
Visit a World-Class 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.
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.
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
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 knowledgeable guides of a hop-on, hop-of 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 (and details on the history of the L), 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.
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.
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.
For a walk that is never the same twice, stroll through these outdoor galleries that house temporary modern art exhibitions, including large-scale sculptures.
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.