Ahhh the Chicago street festival. Now if I said that Lollapalooza was my happy place, I might have forgotten about how much I love street fests. There really is nothing I love more than an excuse to be outside in different neighborhoods of Chicago feasting on local food and cold beer. And throwing in a live band or two never hurts.

Most importantly, I know I’m not alone. Most Chicagoans love the street fest as much as I do, and that’s why there is one (if not more) every single week/weekend of the summer beginning memorial day weekend. Most are free or simply take donations and are a guaranteed way to make the best out of summer in Chicago. Let the fun begin.

In this series of articles we will include a month-by-month guide of what’s up at this summer’s street festivals, including a separate article on Chicago Food Festivals and Chicago Music Festivals. We’ll start with May — the month that likes to tease us with its on and off summer weather. Screw you May, we’ll act like it’s summer anyway.

Cinco de Mayo Festival
When: May 4-6
Where: 26th St. & S. Kostner Ave
Price: Free
Basic Info: Live music, food vendors, arts & crafts, and kids activities celebrate this Mexican holiday.

Chicago Mayfest
When: May 4-6
Where: 3100 N. Ashland. Ashland and Barry, Lakeview neighborhood.
Price: $5 donation
Basic Info: This street fest kicks off street fest season (aka summer) with different live bands each evening, food and beer vendors, and even a pet parade!

Belmont/Sheffield Music Festival
When: May 26-27
Where: 3200 N. Sheffield. Belmont/Sheffield, Lakeview neighborhood.
Price: $5 donation
Basic Info: This festival has live bands at 2pm, 4pm, 6:30pm, and 8:30pm as well as food, beer, and crafts vendors.

Randolph Street Market Festival
When: May 26-27
Where: 1350 W. Randolph, West Loop.
Price: $8 online ahead, $10, $5 for students.
Basic Info: This is a more serious festival, more for the buying crowd and less for the drinking, eating, and listening crowd. This indoor/outdoor market features antiques, indie designer apparel, fancy foods, and vintage collectibles.

Check back June 1st for our June Street Festivals Preview!