Chinatown Summer Fair, White Sox v Cubs, Chicago Sky WNBA - Unwrap a Windy City Weekend

Chicago listeners, get ready for an unforgettable experience in the Windy City—packed with music, art, sports, outdoor fun, culture, and downright amazing food. For something unique this weekend, the Chinatown Summer Fair kicks off July 26 and 27 on Wentworth Avenue. This festival is famed for its dazzling lion dance, live Asian performances, kung fu demos, street food, art vendors, and a real neighborhood buzz. Admission is free, and the event is perfect for families.

If live sports are your thing, Guaranteed Rate Field is the battleground for the Chicago White Sox and Chicago Cubs rivalry on July 26 at 6:10 p.m. and July 27 at 1:10 p.m. For basketball fans, the Chicago Sky face off against the Indiana Fever at the United Center on July 27 at 2 p.m.—a historic WNBA event drawing record-breaking crowds with stars like Angel Reese and Caitlin Clark.

Music lovers can dive into iO Fest 2025 at iO Theater July 26 from 5 p.m. onward, where over 120 global improv and comedy acts take the stage, making it Chicago’s biggest improv event. Hyde Park’s Promontory hosts a Handmade Goods + Music Pop-Up on July 28 from 2–7 p.m., blending local DJs, craft vendors, and South Side flavor. Catch mural masterworks at the “Exquisite Canvas: Mural Takeover” exhibition by Andy Bellomo and others at the Chicago Cultural Center through July 26, transforming gallery walls into a living tapestry.

Outdoorsy types can start their Saturday morning with Millennium Park’s Summer Workouts, stretching and sweating on the Great Lawn until 11:45 a.m. Art fans can stroll through Millennium Park, where Franz West’s “Stonehenge” and “Dorit” sculptures loom amid the cityscape—unmissable for public art enthusiasts. Or cruise the iconic Chicago River with an architecture boat tour, learning how the city’s skyscrapers shaped history while snapping jaw-dropping skyline photos.

Sample Chicago’s global food scene at the Division Street Farmers Market on July 26 from 7 a.m. to noon, where fresh produce, creative eats, and one-off local products abound. For a deep dive into flavor, the Chicago Summer Tequila Tasting Festival takes place July 26 at 2:30 p.m., letting guests sip and savor distinctive tequilas downtown.

Nightlife in Chicago is truly special. Navy Pier’s legendary Summer Fireworks return every Saturday at 10 p.m., with panoramic views best enjoyed along the pier. For an A-list experience, hop on the Tall Ship Windy’s Fireworks Cruise at 9 p.m. on July 26, where you’ll sip a cocktail on Lake Michigan as explosions burst above the skyline. On July 26, the Chicago Water Lantern Festival in Humboldt Park invites you to release a glowing lantern onto the water in a stunning mass display of light and reflection, paired with delicious bites from local food trucks.

Chicago is also teeming with hidden gems. The Messi Experience at 2367 W Logan Blvd is an immersive nod to the legendary footballer’s life, complete with interactive multimedia installations. Locals rave about the Big Bus Hop-On, Hop-Off Tour—running daily from 10 a.m. to 5 p.m.—for hitting downtown highlights and quirky secrets in one seamless loop.

If you’re in the mood to mingle, the Wicker Park Outdoor Vendor Pop-Up on July 27 boasts fashion, baked goods, and Latin food trucks, while West Loop’s CLVR LABs Summer Showcase is an invite-only vendor preview for Chicago’s coolest creators. Both events offer rare finds and genuine local culture.

Art fans—don’t overlook the National Public Housing Museum’s “Living in the Shade” exhibition at 919 S. Ada St., which explores the social impact of open spaces in Chicago’s housing heritage.

Sports fans can look ahead to July 30, when Soldier Field hosts a Premier League Summer Series soccer match—an incredible chance to see world-class football up close.

Foodies and adventurers should add the Taste of Chinatown Food Walking Tour to their must-do list for...