May 2023
- Rosemont Uncorked
- Bark at the Ballpark
- Jazz in the Court
- Millennium Park Summer Workouts
- FACETS
- These Chicago burgers are among the best in America according to Yelp
- Randolph Street Market
- "Van Gogh and the Avant-Garde: The Modern Landscape"
- Bounce The Mall
- Unleash the Bubbles at Pioneer Court
- Heatwave Music Festival
- West Side Story
- Pride Bowl 2023
- Pride Flotilla
- Chicago is a Dollhouse
- Bar Esmé
- The Pitchfork Music Festival 2023 lineup is here
- Taste of Greektown
- Ruido Fest
- My House Music Festival
- West Town Brewing District's Dancing in the Streets
- Pizza City Fest
- Millennium Art Festival
- Roscoe Village Burger Fest
- Silver Room Sound System Block Party
- Pride in the Park
- Logan Square Arts Festival
- Old Town Art Fair
- Maifest
- The best dishes for alfresco dining at Time Out Market Chicago
- Uncle Jerry's Pizza Company
- Nino's Pizzeria
- Louisa's Pizza & Pasta
- Watch movies on a Fulton Market rooftop this summer
- Modernism Road Rally Tour of Homes
- Spring Fun Fest
- Mac's Wood Grilled
- Two Chicago spots are among the 50 best bars in North America
- You'll be able to take a bite out of LEGO-shaped burgers this fall
- The Pearl Club
- Auditorium Theatre
- Duck Sel
- The most luxurious dishes and drinks in Chicago