Explore Chicago's Vibrant Arts, Music, Food, and Sports Scene This Week

Listeners heading to Chicago this week have an array of experiences to dive into, from iconic festivals to unique local treasures. Right now, the Taste of Chicago lights up Grant Park through September 7, offering samplings of legendary deep-dish pizza, gourmet bites, and international treats, plus live music and celebrity chef demos. Over in Edgewater, the Edgewater Music Fest this weekend pulses with over 35 bands, dozens of food vendors, and the feel of an authentic neighborhood block party, making it a draw for music lovers and foodies alike.

Downtown, Millennium Park hosts monumental art installations by Franz West, where sculptures like Stonehenge and Dorit create a dramatic fusion of art and cityscape. For a dose of immersive pop culture, The Messi Experience Chicago on Logan Boulevard offers an interactive journey through the legendary career of Lionel Messi—perfect for soccer fans or families seeking a multimedia adventure.

Tonight and tomorrow, the United Center transforms into a pop paradise as Dua Lipa brings her Radical Optimism Tour to town. For a more spontaneous Chicago experience, Chicago Greeter InstaGreeter Walks give free, hour-long guided tours through the Riverwalk or Loop, starting from the Chicago Cultural Center or Vietnam Veterans Memorial—no reservations required, just show up and soak in the sights.

Sports fans can catch the White Sox at Guaranteed Rate Field through September 21, or seek out Northwestern University’s collegiate action for a taste of Chicago’s sports scene. For a break from urban energy, the Chicago Botanic Garden is alive with blooming displays and special Friday plant giveaways; stroll the seasonal gardens and breathe in the late-summer color.

Outdoor adventurers and photographers should check out the Woods Walks hosted by the Forest Preserve District of Will County, which stretch into November and guide you through serene woodlands on Chicago’s outskirts. If you love uncovering hidden history, John Binder's True Crime: Gangster Tour visits the homes of infamous Chicago mobsters like Tony Accardo and Sam Giancana in nearby Oak Park and River Forest, led by a renowned local historian.

In arts and culture, visit the vibrant outdoor art of the Oak Park Plein Air Festival, where artists paint live across village landmarks, and finished works go on display and sale September 7. If storytelling is your thing, spend Friday evening at Hemingway’s birthplace home in Oak Park for “Fridays at Hemingway’s,” featuring local storytellers sharing “Dear John” tales in a cozy historic parlor.

Classic experiences include the famous Chicago architecture cruise, praised on Tripadvisor for its lively guides and up-close views of architectural marvels on the river and Lake Michigan. Food lovers can savor the Chicago Favorites Ultimate Food and Walking Tour, sampling deep-dish pizza, Chicago dogs, Italian beef, and more, all interwoven with behind-the-scenes tales of the city’s food culture and history.

Throughout the city, pop into the Swap-O-Rama Flea Market in Alsip for vintage finds, or explore art at the Tall Grass Arts Association’s student exhibition in Park Forest. No matter your taste—whether music, art, sports, outdoor escapes, or iconic eats—Chicago this week is a city of possibility, pulsing with both world-famous attractions and hidden gems.

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