The Windy City offers a wealth of cultural and entertainment options that provide attendees with a long list of activities to fill their free time with between meetings. The storied metropolis is brimming with iconic landmarks and revered cuisine and is a popular destination for many local Illinoisans and those from neighboring states like Wisconsin, Minnesota, and Iowa—thanks in large part to its proximity and ease of access. Direct flights to Chicago’s O’Hare and Midway airports are plentiful and typically inexpensive, taking less than an hour and a half by air.
One of the most notable things about Chicago is the famed “L” train system, with its elevated tracks weaving through the downtown—the arteries that pump the lifeblood through the city. As you walk the streets below, the rumble of the train cars overhead is a constant, ever-present soundtrack to the bustling urban life. The electric hum that builds in volume, followed by the thunderous clatter as the cars rattle along the tracks, the air filling with the hissing of brakes. There’s something so old-timey about the rust-covered steel beams, a feeling of nostalgia (perhaps, because they date back to the 1890s). Nonetheless, the rail system sees upwards of 317,000-plus passengers every day.
Whether you’re traveling solo or with colleagues, the sky(scraper) is the limit. You could spend a day exploring the renowned Chicago History Museum, stroll through the striking architecture of the city’s downtown along the river, or take in the energy of Navy Pier. When hunger strikes, you will find an incredibly diverse dining scene, from deep-dish pizza to innovative farm-to-table fare. And for nightlife, Chicago’s hole-in-the-wall bars, comedy clubs, and live music venues provide endless options for evening entertainment.
If you only have a short timespan allotted for exploring the city between networking sessions and keynote speakers, consider this a guide for some exemplary must-dos and must-sees.
Exploring the City
Take a visit to the 360 Chicago Observation Deck, located on the 94th floor of the John Hancock Center. The observation deck offers floor-to-ceiling panoramic views of the city and Lake Michigan from 1,000 feet above the Magnificent Mile. For the more adventurous (and stronger stomached), the TILT experience tilts you out over the city for a thrilling perspective.
For a dose of culture and those in your group that might have an affection for literature, planners can add a visit to the American Writers Museum. This interactive museum celebrates the lives and works of American writers—such as Hemingway, Twain, Steinbeck, and Dickinson—and offers exhibits that delve into the creative process and literary history. It’s an inspiring stop for bibliophiles, and the museum also features group tour rates and on-site venue rentals for events, including its Readers Hall, A Nation of Writers Gallery, and more.
Segway tours are great way to get a unique perspective of the city, while also seeing a lot more sites than walking might allow. Absolutely Chicago Segway Tours offers two-hour tour options that let visitors glide through the bustling streets and along the lakefront, stopping at Millennium and Grant parks, Buckingham Fountain, and the Museum Campus (which, arguably so, offers one of the best hidden-gem views of the Chicago skyline). The guided tour provides insightful commentary on Chicago’s history and architecture, making it both an informative and fun way to explore. Most tours have age restrictions for Segway riders, but bike rentals are a great alternative for attendees bringing their families with younger children along.
Nightlife and Entertainment
Chicago’s nightlife is as dynamic as the city itself, with plenty of options to keep you entertained long after the keynote speakers and breakout sessions conclude. Pizzeria Due is the little brother of renowned Pizzeria Uno, exuding an old-school atmosphere as the eatery dates back to 1955. The walls are lined with antique memorabilia, Shakespeare quotes, and black-and-white marquee photographs. Known for its Chicago-style deep-dish pies, Pizzeria Due also serves up locally made cider, and eventgoers might also while watch a variety of programs on the bar TVs.
A fun group outing might include a visit to The Second City, Chicago’s legendary comedy club. Known for launching the careers of many famous comedians—including Chris Farley, Tina Fey, and Steve Carrell—The Second City offers hilarious performances that will leave you in stitches. Whether you’re a fan of improv or sketch comedy, the talent and wit on display are impressive. The venue can also host private meetings and events on-site.
After the show, you might grab a drink at Snickers, a cozy corner bar that has the vibe of an elevated American Legion (ambient lighting, yet inviting). The bar prides itself on offering an extensive range of drinks, from classic cocktails and craft beers to fine wines and nonalcoholic options, ensuring there’s something for everyone—and the cocktails are cheap, too.
Must-Eats
Bring attendees to these Chicago specialties between meetings, or host your event on-site at any one of them.
The Dearborn
145 N. Dearborn St.; thedearborntavern.com
Tall ceilings, tile-lined walls, and ample window seating abound at The Dearborn—and the food is equally as big on flavor. Try the famous flaky, yet crispy Fish and Chips—Chef Aaron Cuschieri actually beat Bobby Flay with his recipe. Don’t forget to order the Parker House Rolls, served with duck fat butter. For dessert, their beignets rival New Orleans’ Cafe du Mond. Private events of up to 35 seated can be arranged in The Dearborn’s Rialto Room.
Robert’s Pizza & Dough Co.
465 N. McClurg Court; robertspizzacompany.com
For pizza lovers, a visit here is a must. Renowned for its perfect crust and creative toppings, Robert’s Pizza is a delightful experience for any palate. Try the meatballs, a combo of veal and beef, plus red sauce and giardiniera. Next up was the Carne pizza, topped with crumbled fennel sausage, meatballs, cup and char pepperoni, and fresh mozzarella. The waterfront location adds to the charm, offering picturesque views as you savor your meal. Planners have several options for organizing an event here, with private dining rooms and full buyout options available.
Bar Sol
700 E. Grand Ave.; barsolnavypier.com
If you’re seeking seafood, head to Bar Sol. This eclectic eatery on Navy Pier serves a fusion of Latin and American cuisines, with an array of small plates and craft cocktails. Try the chips and homemade hot salsa appetizer; and the fajita platter, which included steak (you can also choose chicken or shrimp), chimichurri potatoes, black beans, guac, and salsa. The vibrant decor and lively ambiance make Bar Sol a great spot for private gatherings, with on-site spaces available including its main ballroom, two private party rooms, and a VIP room.
Gene & Georgetti
500 N. Franklin St.; geneandgeorgetti.com
No trip to Chicago is complete without excellent Italian food, and Gene & Georgetti does not disappoint. Established in 1941, it’s the longest running Italian steakhouse in Chicago. Try the Gnocchi alla Norma, which features homemade gnocchi, sauteed eggplant, basil, and creamy mozzarella di bufala. The Prime NY Strip is char-broiled to perfection—and shareable. Lastly, the Chicken Joe is a steaming heap of juicy roasted chicken with sweet and hot peppers. It’s named after a Gene & Georgetti waiter from the ’70s and has been on the menu ever since. Planners can bring their groups here for private dining experiences of up to 90 people.
