Laugh, shop, sip: Chicago's top events

Experience vintage shopping, a wine walk, comedy and more!

😆 D.L Hughley

• Laugh alongside the stand-up comedian and actor.
• Friday and Saturday 7 and 9:30pm and Sunday 6pm at Chicago Improv in Schaumburg.
• Tickets start at $40

🎨 West Town First Fridays

• Stroll through the neighborhood's many galleries, including an exhibition curated by artists at Esperanza Community Services.
• Galleries stay open until 8pm and later.
• Free.

🚚 Food Truck Festival

• Sample everything from shaved ice to jerk chicken, funnel cakes and more.
• At Naper Settlement in Naperville.
• Tickets start at $10, free for kids 10 and under.

🛍️ Oddities Flea Market

• Discover unique treasures, including handcrafted jewelry and art.
• Saturday and Sunday 11-6pm at Morgan MFG in Fulton Market.
• Tickets start at $25.

🍷 Andersonville Wine Walk

• Celebrate the event's 20th year by strolling through the North Side neighborhood with a glass of wine in hand.
• Sunday 3-6pm in Andersonville.
• Tickets are $50.

🧺 Wicker Park Farmer's Market

• Feel the summer vibes at the opening day of the neighborhood market as you shop baked goods, local art, produce and more.
• Sunday 8am-2pm in Wicker Park.
• Free.

🎶 The October Nights Tour: Calling All Lovers

• Grab tickets for a R&B concert featuring October London, Tamar Braxton and Ro James.
• Sunday 7pm at the Chicago Theatre in the Loop.
• Tickets start at $53.50.