April showers bring May flowers. May flowers bring Chicago’s festival season. Now that may not be a real saying but it might as well be. There are few things in this city that evoke excitement quite like being on the front doorstep of festival season. Whether it be music festivals like Lollapalooza or Heatwave, food festivals such as Windy City Smokeout or the Taste of Chicago, or your every-weekend neighborhood street fest like Do Division or Wicker Park Fest; this city has no shortage of outdoor activities for families of all sizes.

We have your breakdown of all things Chicago Festival Season. You’ll be able to bop around UrbanMatter as your one-stop shop for festival round ups, detailed ticket giveaways, lineup breakdowns, food vendor spotlights, and more. If it’s going on in Chicago this summer, you can check it out and maybe come say hi…we like beer!

That being said, here’s your Chicago Festival Guide for May 2023. Cheers!

Mexico Fest

When: May 5-7th | Where: Navy Pier | Editor’s Take: A family-oriented pier festival free of charge with live performances and creative workshops for kids. 

Manifest Urban Arts Festival

When: May 12th | Where: Columbia College | Editor’s Take: A righteous festival-like setting aimed to celebrate young, talented artists and creatives of all types. 

Chicago Mayfest

When: May 12-14th | Where: Lincoln Square | Editor’s Take: A proper re-introduction to Chicago’s summer season with great food, drinks, and live music. 

Mole de Mayo Festival

When: May 26-28th | Where: Pilsen | Editor’s Take: A relatively new festival that seemingly grows every year featuring a super cool open air market and lots and lots of delicious mole. 

Belmont-Sheffield Music Fest

When: May 27-28th | Where: Lakeview | Editor’s Take: One of the more classic North side festivals great for listening to tribute bands and drinking good beer. 

Sueños Festival

When: May 27-28th | Where: Grant Park | Editor’s Take: A two-day party celebrating everything Latin culture in one of Chicago’s most iconic festival locations. 

Featured Image Credit: StarEvents

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