Chicago skyline landscape

A Lawyer's Guide to Chicago

 | DRI
Updated February 13, 2024

The Windy City offers something for every lawyer – on and off the clock.

Everyone needs a break from the grind of their job, and lawyers are no exception. A legal hub for some of the top firms in the country, Chicago is also one of the best cities in the world for embracing culture, art, history, and recreation. From fine dining in the Loop to water sports on Lake Michigan, there’s something for every lawyer in the Windy City. Next time you’re in town for a conference or interview, or if you already live and work in the city, we encourage you to explore all there is to see in Chicago’s unique neighborhoods.

Check out the guide below for some of the best activities for lawyers in Chicago and plan your next visit today!

Lion statue Art Institute Chicago

Museums & Art Galleries

Chicago has a long history of art and culture, and you can see it on display at any number of museums and art galleries throughout the city. From the iconic Field Museum of Natural History and the Art Institute of Chicago to smaller galleries like the Zhou B Art Center in Bridgeport, you can find plenty to do and see here. For those who prefer modern art, The Museum of Contemporary Art is also worth a visit and located just down the block from Chicago’s iconic Water Tower. If aquatic life is more your speed, be sure to check out the Shedd Aquarium, conveniently located on Chicago’s Museum Campus! Many of the city’s museums offer free days, as you can see on this list from Choose Chicago.

Landscape of Lincoln Park Zoo

Outdoor Activities

If you’re lucky enough to plan your visit during the warmer months, Lake Michigan is the perfect place to relax and unwind after a long day. There are plenty of beaches to choose from—whether laying in a hammock with a book or renting a paddleboard is more your speed. Even in the colder months, the Chicago Riverwalk or the lakefront are great places for a walk or a jog—just keep an eye on the weather! If you’re more of a biker, the North Branch Trail or Bloomingdale Trail (otherwise known as the 606) are perfect for a long ride. Get your steps in by window shopping up Chicago’s Magnificent Mile on Michigan Avenue, or take a stroll through the Lincoln Park Zoo, which is free for everyone!

Restaurant scenery

Culinary Scene

Chicago is more than just deep-dish pizza and hot dogs; it’s home to many world-class restaurants featuring cuisines from across the world. Visit an experimental Michelin Star restaurant, hit Chinatown for the best authentic dim sum, or grab a Chicago-style hot dog from the nearest Portillo’s—the city is your oyster! When it comes time to finish off your night, be sure to check out some of Chicago's legendary music venues such as The Empty Bottle or The Metro, where you can listen to local bands, or catch a late-night comedy show at The Second City. Did you know that Chris Farley, Tina Fey, Tim Meadows, and Stephen Colbert, among many other legends, all performed on The Second City stage?

Soldier Field landscape chicago

Sporting Events

No matter what time of year you visit, you’ll have the chance to catch a Chicago professional sports team in action! Visit the United Center for a Chicago Bulls or Blackhawks game or cheer on the Bears at Soldier Field. During baseball season, catch a Cubs game at the iconic Wrigley Field or head south for a White Sox game. Going to a sporting event is a great thing to do as a work event—be sure to check out group deals on tickets. No matter what team you root for, the energy Chicago sports fans have is contagious!

Chicago downtown buildings landscape

A World-Class Legal Community

Chicago is the proud home of DRI, the largest international membership organization of attorneys defending the interests of business and individuals in civil litigation. During March, DRI is presenting several top-notch seminars that you can attend to build your business and experience firsthand the lively legal community found in Chicago. But don’t take our word for it – see for yourself by checking out DRI’s upcoming seminars!

Whether you're looking for an afternoon spent exploring museums or an evening spent enjoying food and drinks at one of Chicago's famous restaurants, there's no shortage of fun things for lawyers in this city! With so much diversity in its offerings – from shopping on Michigan Avenue to cheering the Cubs on – there's truly something here for everyone. So, grab your friends (or colleagues) and head out into this vibrant city for an unforgettable experience!

Not from Chicago? Don’t worry – DRI offers events across the U.S., as well as virtual programming, throughout the year. Learn more about our upcoming events.

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