“Chicago is constantly changing; there’s constantly innovation here, even with our established institutions like the Art Institute of Chicago, among others,” Choose Chicago’s new President & CEO Kristen Reynolds tells Recommend.
“Coming up next year,” Reynolds continues, “is America’s 250th Anniversary [with celebrations taking place in Chicago] and the centennial of Route 66,” which starts in this Midwest city and runs all the way to Santa Monica. “We have the Obama Center opening [in 2026],” she adds. There’s also the Bally’s casino resort coming up, which, as of press time, will encompass a 500-room hotel tower, six restaurants, cafes and a food hall, a rooftop restaurant and bar, a 2,000-ft.-long publicly accessible riverwalk and an onsite casino.
Reynolds notes that the city’s visitor numbers are heading toward pre-pandemic levels: “We’ve had some really great momentum this year, with a lot of record-breaking occupancy weekends. I feel like Chicago is a city that is really hungry for the business, and they understand the connection between tourism and visitation to the economy.”
She says that her first impressions of Chicago have been that “it’s friendly and beautiful, but also vibrant, cultural and eclectic. There are so many layers to this city.”
We recently got to experience of few of Chicago’s “layers.” Here are 5 not-to-miss:
1. I hopped on ToursbyLocals’ “The Bear”-inspired Ok, Chef! tour, guided by a local who knows every corner of this stunning city. Aside from, of course, stopping in at Mr. Beef and sampling those famous sandwiches, we also visited filming locations that have been showcased in the series, drove into lesser-known neighborhoods, viewed some of Chicago’s famous murals and got insider tips on the best dining spots in town—from local bakeries (Chi Quon Bakery in Chinatown) to some of the best BBQ joints (The Tonk), not to mention Pilsen Yards for tacos. Like our knowledgeable, personable, engaging and fun tour guide told us, “In Chicago, you can spend days just eating.” One of Jeremy Allen White’s favorite restaurants? La Scarola.
2. Have clients who love “Saturday Night Live”? Then Second City, an improvisational theatre and comedy troupe founded in Chicago, is a must-stop. This is where many SNL cast members and writers—ranging from Gilda Radner to Tina Fey—trained and performed before joining the show. The theater is arranged cabaret-style, creating an intimate setting where the ensemble interacts with the audience as guests enjoy small bites and drinks.
3. Baseball fans will want to head to Wrigley Field, of course, as it’s MLB’s second-oldest ballpark (built in 1914). And yes, it’s a very cool place to catch a baseball game, but why not recommend your clients head to one of the Wrigley Rooftops, 16 residential rooftops outfitted with bleachers and F&B served with a side of amazing views.
4. Chicago is known for making a splash on the big screen and the “sets” came to life for me (a huge film buff) during the 2-hour On Location Tours’ Downtown Chicago TV & Movie Sites tour. We hopscotched across downtown, taking in the Art Institute of Chicago and Federal Plaza (“Ferris Bueller’s Day Off”); Chicago’s Union Station and the lobby of The Roosevelt University (“The Untouchables”); LaSalle Street (“The Dark Knight,” “Batman Begins” and “Home Alone 2”); and Richard J. Daley Plaza and City Hall (“The Blues Brothers”). By the way, art lovers will want to know that the two aforementioned plazas are home to a Calder sculpture and a Picasso sculpture, respectively.
5. I might not have been able to check out the American Writers Museum while in town, but I did get the scoop on this spot from a local and it’s definitely on my to-do list next time around. Located in the heart of downtown just steps from Millennium Park, it’s the only museum in the nation dedicated to celebrating American writers. Museum-goers will find interactive experiences, including typewriters where they can craft their own story, as well as engaging exhibits such as “American Prophets,” which explores the intersection of religion and writing and opens Nov. 21.
