Chicago Street Festivals: May

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 is 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 6-8
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 20-22
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 28-29, 12pm-10pm.
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 28-29, June 25-26; July 30-31; Aug. 27-28; Sept. 24-25
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!

Tessa McLean

About Tessa McLean

There is just something about that feeling when you have been away — maybe for a weekend, a month, 6 months — and you’re driving into Chicago and that first glimpse of the city skyline appears. It just always makes me smile.

One Comment

  • Jesse Smith
    May 26, 2010 | Permalink | Reply

    I concur with both points: 1) street fairs rock AND 2) screw you May.

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