Best things to do when travelling on business to Chicago

Known by several nicknames – including The Second City, The Windy City and The City of Big Shoulders – Chicago is the business capital of the Midwest and an economic engine that’s home to major financial exchanges, Fortune 500 companies such as JLL, Kraft Heinz and McDonald’s, plus more than 6,000 tech start-ups. It’s also a cultural powerhouse, with world-class architecture, museums and performing arts institutions. This is how to make the most of your time there.

Where to start

Chicago’s central business district is known as The Loop and gets its name from the shape formed by the train lines that encircle it. Framed on two sides by the Chicago River and on one side by Lake Michigan, this downtown area is home to some of the city’s top attractions: the green spaces of Millennium Park and Grant Park , The Art Institute of Chicago ’s incredible collection, and architectural landmarks like the Willis Tower , The Rookery and the Chicago Board of Trade Building . Directly to the west, two formerly industrial neighbourhoods, the West Loop and Fulton Market , are now filled with hip restaurants, bars and hotels, not to mention the offices of companies like Google. 

Where to take clients

Chicago is a big sports town, so consider taking your clients to an ice hockey, basketball or baseball game. Depending on the season, you can catch a Blackhawks or Bulls game at the United Center or a Cubs game at iconic Wrigley Field , the second-oldest baseball ground in the country. For meals, steakhouses are always popular. There are many to choose from, but Chicago Cut Steakhouse is a safe bet with its timeless charm and river views, while RPM Steak has a glitzier, more contemporary vibe. 

Of course, there’s more to the city’s dining scene than just steakhouses. For fine dining to impress, Oriole and Smyth are both Michelin-starred spots in the West Loop with tasting menus that are constantly changing. For something more casual in the area, Trivoli Tavern is an American-style pub with a fun atmosphere and wide-ranging menu; alternatively, Aba features skyline views and Mediterranean-inspired dishes. For drinks, make a reservation at The Office , an intimate speakeasy serving classic cocktails and vintage spirits. If the weather is nice, grab a table on the terrace of Z Bar , which overlooks the famous Magnificent Mile. 

Where to stay

The city’s best hotels are located downtown along the Magnificent Mile and in The Loop and West Loop. Claim bragging rights by staying at The St. Regis Chicago , the city’s newest five-star stunner designed by celebrated architect Jeanne Gang. Located on the bustling riverfront, LondonHouse Chicago offers spectacular views and an extremely popular rooftop bar. Directly across the street from Millennium Park, the Chicago Athletic Association is an elegant hotel occupying what was once a private members’ club; its multiple restaurants and bars are well worth a visit. In the West Loop, Nobu Hotel Chicago features sleek, minimalist rooms with luxury touches. 

What to say

Stimulate intelligent conversation by asking for opinions on the current temperature of Chicago’s business environment. For something lighter, ask where to find the best pizza, hot dog or Italian beef sandwich – and prepare for a variety of passionate responses. 

What to know 

Chicagoans take a great deal of pride in their city, coupled with the pervasive feeling of being underrated in comparison to New York and Los Angeles. You’ll endear yourself to locals by sharing genuine praise for Chicago and all that it has to offer. Also, don’t be surprised if your clients or colleagues urge you to drink a shot or two of Jeppson’s Malört, a bitter-tasting liqueur that’s considered a rite of passage for first-time visitors. 

Downtime done right

If the weather is pleasant, hop on a 90-minute Chicago Architecture Center River Cruise (runs between March and November), during which you’ll learn all about the impressive skyscrapers lining the Chicago River. For high-end shopping, head to the northern stretch of Michigan Avenue known as the Magnificent Mile . In the mood for museums? The Art Institute of Chicago is home to some of the world’s most famous artworks, while The Field Museum features historical artefacts and wonders from the natural world. If it’s a clear day, take in the incredible view from Skydeck Chicago on the 103rd floor of the Willis Tower, the city’s tallest building. 

Take something home 

For books, games, toys and gifts inspired by the city, head to the gift shop at the Chicago History Museum . If you enjoyed that taste of Jeppson’s Malört, why not bring a bottle home? Find it at Binny’s Beverage Depot or any store selling spirits. For another local speciality, grab a jar of pickled spicy peppers, known as giardiniera, from sandwich shop Potbelly .