Chicago Means Business: Where to Stay, Meet, and Dine in the Windy City

Is there a more American city than Chicago? Set in the middle of the country, on the shores of Lake Michigan, the Windy City serves as a beacon of industry, creativity, and diversity and exemplifies a can-do spirit. With a population of more than 2.7 million, it’s no longer “the Second City”—that would be Los Angeles—but over 9.6 million people in the 13 counties across Northern Illinois and Northern Indiana that make up Chicagoland call it home. It’s the birthplace of the skyscraper, the refrigerated railcar, even the TV remote control, and it serves as the headquarters of 400 major corporations, including McDonald’s, Allstate, United Airlines and Blue Cross Blue Shield. It’s no wonder that one of Chicago’s other nicknames is the City That Works.

Airports

Two major airports serve the city: Chicago O’Hare International Airport, on the northwest side, and Chicago Midway International Airport, on the southwest. In 2024, O’Hare was ranked the second-busiest airport in the world for aircraft movements (776,036) and the eighth busiest in the world for passengers (more than 80 million). It’s a major hub for both United Airlines, which has a 40-percent market share, and American Airlines, which has a 22-percent share.

Hall of Flags at Chicago O’Hare International Airport / Photo: Rosamar/Shutterstock

This year American is launching Chicago flights to Naples, Italy, Madrid and Halifax, Canada. United also added a flight to Halifax, as well as two domestic offerings: Billings, Montana, and Ontario, California.

Midway, meanwhile, served more than 21 million passengers in 2024 and has approximately 210 daily flights. Southwest Airlines carries more than 90 percent of Midway’s passengers, and some of its most popular routes include New York City, Phoenix and Orlando, Florida.

Founders Suite at the Chicago Athletic Association hotel / Photo: Courtesy of Chicago Athletic Association Hotel

Business Hotels

If you’re working downtown, you’ll want to book at The St. Regis, which opened at the mouth of the Chicago River in 2023, forever changing the city skyline. (At 101 stories, it’s the tallest skyscraper in the world designed by a woman, Jeanne Gang.) The service is impeccable, the views are unparalleled, and the tagliatelle al ragù at chef Evan Funke’s Tre Dita is scrumptious. For a more unbuttoned vibe, try the Chicago Athletic Association, across from Millennium Park. Built in 1893, it was an exclusive athletic and social club until 2007 and then was transformed into a hotel in 2015; it joined the World of Hyatt in 2019. The stately property has 240 rooms and suites and plenty of places to entertain clients—from the vibrant rooftop restaurant Cindy’s to the city’s first Topgolf Swing Suite. You can even hold an event in the Association’s old basketball court.

Various dishes at Maxwells Trading / Photo: Courtesy of Jeff Marini

Power Meals

Chicago was a food city long before The Bear came along. Now it’s just harder to score a table. Two hotspots in town are Maxwells Trading, whose wonderful mixed bag of a menu offers everything from pear and Taleggio tortelloni to pork katsu (and earned its chefs a 2025 James Beard nomination), and Fire, a relatively affordable tasting-menu spot celebrating open-fire cooking from culinary wizard Grant Achatz.

Don’t overlook classic restaurants, though. For a killer filet mignon and impressive Italian-heavy wine list, head to Gene & Georgetti, which has served everyone from Frank Sinatra to Mariah Carey in its 85 years. If you have a big group, book a table at the always popular Frontera Grill, Rick Bayless’ original Mexican restaurant, which is even more delicious than it was when it opened in 1987.

Conference Centers and Venues

McCormick Place is the largest convention center in America. With 2.6 million square feet of exhibition space, it hosts everything from the Chicago Auto Show to the Comic and Entertainment Expo to the NBA draft lottery. Four buildings house 173 meeting rooms, four ballrooms and a high-tech event center, and there’s also the 10,000-seat Wintrust Arena and historic 4,188-seat Arie Crown Theater.

Chicago / Photo: Courtesy of Roy Johnson/Alamy Stock Photo

With its Ferris wheel and fireworks, Navy Pier is one of the city’s biggest tourist attractions, but it’s also a scenic place for a convention. Its Festival Hall has more than 170,000 square feet of exhibit space and 36 meeting rooms. The Aon Grand Ballroom, meanwhile, serves as a stunning location for a 1,100-person dinner, thanks to its 80-foot domed ceilings and sweeping lake views.