Chicago Mixtape

If Chicago’s streets could talk, they’d regale you with tales of the countless musical icons who have performed at the city’s storied clubs and venues — and the lucky few who began their illustrious careers in the Second City.

To properly experience Chicago’s music scene, you’ll need to embrace a night owl mentality. To prepare, we begin our adventure with a hearty lunch.

Dine among a massive collection of autographed guitars, legendary costumes and other music memorabilia at the famous Hard Rock Cafe, or enjoy the Caribbean vibe of Havana Grill, which offers a seasonal patio that looks and feels like a tropical oasis. 

Next, book an afternoon show at the world-renowned Chicago Symphony Orchestra. Close your eyes and listen, and you’ll understand why these moving performances frequently win international awards. 

Just outside the venue, you’ll find the landmark street sign that marks the beginning of historic Route 66. Walk a block or two up Michigan Avenue, and you’ll see the Jay Pritzker Pavilion, a beautiful amphitheater that regularly hosts free outdoor concerts during the summer months.

After a leisurely stroll through downtown Chicago, you’ll be ready for dinner and a show. If you head to Andy’s Jazz Club & Restaurant, prepare to be serenaded by some of the area’s top talent as you munch on anything from steak to pasta. 

If you opt for Carnivale instead, you can expect an evening of flavorful Latin-inspired cuisine and one-of-a-kind performances featuring South American and Afro-Brazilian music, feathered showgirls and stunning salsa dancers.

Country music lovers may want to eschew the aforementioned options for Bub City, which dishes out quality whiskey and barbecue to go with the live, upbeat tunes that typically attract a crowd to the dance floor. 

Hopefully dinner left you feeling reinvigorated, because the night is far from over. Are you familiar with the term, “nothing good happens after midnight?” Well, these places prove that old adage is wholly inaccurate. 

At The Hangge-Uppe, you can dance until your legs give out — or until closing time at 4 a.m., whichever comes first. Kick it to today’s hits in the upstairs area, or sing along to classics from the 70s and 80s on the wild-and-crazy lower level.  

If you’re lucky enough to score a coveted seat around the piano at The Redhead Piano Bar, you may want to hold onto that spot until the wee hours. And for those who prefer the nightclub scene, check out The Underground, a vibrant hotspot frequented by celebrities. 

When it’s time to finally succumb to the lure of a comfortable bed, you’ll have a variety of choices. The ACE Hotel Chicago offers modern digs in the West Loop, with two year-round rooftop bars and an indoor cafe for farm-fresh food. 

Or stay downtown at the Virgin Hotel Chicago, a reimagined boutique with a restaurant, bar and live music performances on some nights. Of course, you can always go with the ACME Hotel as well, conveniently located in the middle of the action in the River North neighborhood. 

If you’re still having trouble deciding on a hotel, no worries, just continue your search!

Today isn’t the day to feel guilty about a late start — you deserve a sleep-in after last night’s epic outing. 

The morning kicks off on the city’s South Side. Take a walk through Bronzeville, a historic neighborhood that’s home to the residence where the late, great Louis Armstrong spent several of his formative years. While in the area, you can stop by the future site of the National Museum of Gospel Music, where the former Pilgrim Baptist Church is being transformed into a state-of-the-art cultural institution. 

For another dose of Chicago culture, let’s head up the street to Chinatownfor lunch. The culinary scene in this vibrant Chinese American community is remarkable, with everything from authentic bakeries to dim sum spots and barbecue restaurants. If you’re feeling bold and theatrical, you’ll find that several establishments are famous for their karaoke offerings as well.

Speaking of theatrical, how about a Broadway in Chicago matinee? Choose a particular show or your favorite venue in the elegant Downtown Theater District, and enjoy a spectacular performance you won’t soon forget.

For the evening, you’ll have the option to choose your own adventure. Boogie down to Pilsen for a night at Thalia Hall, a neighborhood landmark that combines historical charm with a modern flair. Before catching a show at the intimate venue, grab dinner at the elegant but unassuming Dusek’s, which is part of the same building. 

The fun doesn’t end with the show’s final note — after the performance, head upstairs to the Tack Room, a cozy cocktail bar where you’ll likely discover a pianist banging out fan favorites deep into the night. 

Or, perhaps, you’ll choose to venture to the South Loop to kick off your evening at Reggies Chicago. What was once a dilapidated auto bumper repair shop has morphed into a bustling destination for those looking to experience cutting-edge bands and other exciting events.  

Indefatigable types can continue the fun at Buddy Guy’s Legends, the premier blues club owned by the Rock & Roll Hall of Famer himself. Both Reggies and Buddy Guy’s are known for their food, so make sure to eat your fill before all that grooving and head bopping.