What to Do on a Day in Chicago

Chicago is one of the world’s great cities. That means finding things there for one day is both easy and a challenge. Easy, because there’s so much. Challenging, because you don’t have the time to do it all!

The perfect Chicago day trip is different for everyone. But there are some things that any visitor should experience if they can. Here are some of the best.

Take in the downtown architecture

Chicago is renowned for its architecture. It’s one of the easiest things for you to enjoy on a day in the city, because wherever you turn, you’ll see something to impress.

Just getting to know the city on foot is a fun way to spend a day. But if you want the highlights, visit the Chicago Architecture Center or take an architecture river tour with Shoreline Sightseeing or Wendella Sightseeing.

Eat the local delicacies

Name a cuisine—Chicago does it all. From street food to fine dining, you will not go hungry or unsatisfied during your day in the city.

But for the true Chicago experience, it’s worth trying food the locals invented. So use the opportunity to try the Chicago Hot Dog, Deep Dish Pizza or Italian Beef.

Explore the Art Institute

The Art Institute of Chicago by @agentlewoman

The Art Institute of Chicago is consistently rated among the world’s top museums by TripAdvisor users. Once you see its collections, you’ll understand why. Must-see highlights include Edward Hopper’s Nighthawks, Grant Wood’s American Gothic and Georges Seurat’s A Sunday on La Grande Jatte.

Visit Millennium Park

Overlooking Millennium Park in Chicago - by @mattbweitz

Millennium Park is a remarkable outdoor park, free to the public, bringing together architecture, landscape, design and art. It might be Chicago’s most popular outdoor spot, attracting five million visitors a year. Many come for the concerts and festivals, but no matter what day or time of year you’re there, you’ll discover a whole lot of amazing sights and photo opportunities.

Cloud Gate (fondly referred to as “The Bean”) is its most well-known attraction, but you’ve also got to check out the Jay Pritzker Pavilion and Crown Fountain, a spectacular blend of water, video and interactive art.

Shop the Magnificent Mile

Got some shopping to do? There’s no better place in Chicago than The Magnificent Mile. You’ll find all the big-name brands, boutiques, department stores and luxury labels lining a magnificent avenue stretching 13 blocks, and a square-mile outward. But remember, you’re pressed for time, so make those purchases worth it!

See the animals at Lincoln Park Zoo

Lincoln Park Zoo by @genericsteve

A visit to the Lincoln Park Zoois an easy choice. Admission is free, it’s located in beautiful surroundings and it provides a home to more than 200 species. Don’t miss the great apes or polar bears.

Catch a Chicago sports team in action

Wrigley Field by @stevegogreen

Chicagoans love their sport. You’re unlikely to walk down a street without seeing a flag, a cap or a sticker promoting one of the city’s winning teams.

What you can see depends on the time of year and the teams’ schedules. But do your very best to catch either the Cubs at Wrigley Field (baseball), the White Sox at Guaranteed Rate Field (baseball), the Bears at Soldier Field (football), or the Blackhawks (ice hockey) and Bulls (basketball) at United Center.

Watch some improv

Chicago is renowned for its improvisational comedy scene. Its theaters and schools have turned out some of America’s best-known talents over the past half century. Catch the next superstars at the world-famous Second City or iO.

Ascend a tower

Watching over the city from the Willis Tower Skydeck by @mayaramverhulst

Take in spectacular views of the city from the top of two of Chicago’s tallest buildings. The Skydeck is on the 103^rd story of the 110-story tall Willis Tower (formerly Sears Tower), Chicago’s tallest building. 360 Chicago sits at a similar height in 875 North Michigan Avenue (formerly John Hancock Center). Both provide a perspective of the city you just won’t get at street level. If you can, time it for sunset. You’ll get to see the city at its finest, both in daylight, and lit from within. It might just happen to be the perfect way for you to end a day in the Second City.

Chicago from Chicago360 by @relatablered