It's a cool night, a slight breeze blowing through your hair. The tranquil waters of Lake Michigan move around your boat in gentle waves. You raise a toast as the sun slowly sets from behind one of America's largest skylines.
The backdrop of the city is familiar, but the vibe is different – clean, modern, purposeful. And the people, they can’t wait to show you around, or tell you a story from the streets of the Windy City. This is Chicago, a town brimming with hometown pride.
As you continue to float serenely through the water, downtown buzzes around you, alive with nightlife, award-winning food, and world-class music. As your tour guide regales you with stories about how Mrs. O’Leary’s cow started a citywide fire in 1871, it doesn't take long to understand that the Second City isn’t like any other city. Chicago musician, Mike Ledbetter, captures this moment best. “There’s a beauty to Chicago that includes a marriage between stunning architecture surrounded by nature, art and the grittiness of a weathered, storied city.”
You can find the city’s flag waving from buildings, tattooed on forearms, and emblazoned on---well, everything. People here know their history, and that history is deeply entwined with the blues. “Music is about telling a story, and there’s no better way to do that than by singing the blues,” Ledbetter states.
During the Great Migration, 500,000 African Americans left the rural south and moved to this Midwest city, often taking jobs in factories. Clubs like the Dreamland Ballroom were more elegant than their southern counterparts, and the music stepped up to the challenge. Building off of the familiar sounds of homegrown blues, jazz, and gospel, Chicagoans began to include instruments like the electric guitar, drums, and piano; musicians began to perform solos on stage. The new style was given a new, groovier name: Boogie Woogie.
Chicago is still home to many local blues musicians, and there are plenty of historic venues dedicated to the craft. If you’re interested in the jazz and slam poetry scene, make sure to hit the Green Mill. And, if you’re just looking for a laugh, you can grab tickets for a night of improv at Second City.
Checking out blues memorabilia with Lurrie Bell
Chicago, like most cities, is full of incredible talent, from the street musicians on Michigan Ave to dancers at the Joffrey Ballet. Chicago, unlike most cities, has a famous improv and sketch comedy scene that continues to thrive to this day.
The Second City opened its doors in December of 1959. Second City success ignited a trend for more performance spaces to open in the city. The talent that graced the stage became some of our most beloved television and movie stars, like Bill Murray and Tina Fey.
Today, The Second City prepares the next generation of comedy titans by hosting classes and workshops. If you can’t snag tickets to the Mainstage or E.T.C. shows, you’ll still be able to drop in and watch different levels of talent perfect their craft.
If you’d like to see a wider sampling of what Chicago performers have to offer, Stage 773 is a hub for comedy festivals. You can grab tickets to the Chicago Sketch Comedy Festival in January, the Chicago Women’s Funny Festival from May to July, and the Chicago Nerd Comedy Festival in May. It’s also home to the city’s longest-running musical comedy, Cupid Has a Heart On, and features a curated selection of independently produced showcases.
Ledbetter reflects, “Chicago is a little bit of everything rolled all into one. It has the big city feel, but it has the small-town kind of family feel to it. Chicago is all about attitude, too. It's fierce, in a good way.” And he’s right. Chicago has interactive art like Cloud Gate, also known as the Bean, and Crown Fountain. There’s a giant Picasso sculpture in Daley Plaza and a huge set of iron legs in Grant Park. There are beaches and a riverwalk and Ferris wheels and deep-dish pizza and a baseball team that overcame a 71-year curse.
Mike Ledbetter, framed by Chicago's iconic architecture
More experiences nearby