Retro on Roscoe is widely recognized as one of Chicago’s best street festivals of the year. It has all the necessary components of a irresistibly good time. With live music, artisan tables, food vendors, plus the famous Windy City Chili Cook-Off, there won’t even be enough time for you to get bored! A vintage care corner and a great kids’ area, open noon to 6 p.m. both days, with balloon artists, inflatables and face-painting makes for a great family outing as well.
This classic fest combines some of the country’s best children’s entertainers with some of the city’s best rock cover bands all compiled within a four-block radius of each other on Roscoe Street west of Damen Avenue. Past children’s stage performers have included top-notch acts such as Justin Roberts and Ralph’s World. And as if that weren’t enough, last year, the kid’s corner featured a fully operational miniature Ferris Wheel that gave provided quite the joyous experience for the little one’s.
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