The Best Chicago Street-Festival Dates

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If Chicago summers could be defined by one thing (excluding the sweltering heat and suspicious influx of hot-dog stands), it’d be street festivals. Beginning in May and running through early September, the sheer number of events per weekend is enough to send even the savviest among us into an indecisive tailspin.

After sifting through schedule upon schedule, we’ve determined which festivals have the best summer-date vibes, and of course, which ones are sure to set the scene for mixing and mingling.

Chicago Craft Beer Festival – June 21-23

St. Michael in Old Town
1633 N. Cleveland Ave.

Though it’s only in its second year, this brew-enthusiasts paradise is the ideal place to take a date who knows a thing or two about hops (or, you know, someone who wants to learn). With tents hosting over 100 specialty-beer tastings from favorites like Jolly Pumpkin, Lagunitas and Virtue Cider, the drinks alone make for fantastic conversation starters.

Chicago Pride Fest June 21-23


One of Chicago’s most anticipated events of the summer, Pride Fest boasts every element of the perfect festival – the three F’s (friends, food, and fun), hundreds of bars with great drink specials, and of course, the opportunity to dress head-to-toe in neon without having to endure a Deadmau5 set in the process.

West Fest July 13 & 14

West Town 

With live music from acts like Javelin and Born Ruffians (booked by the always-fantastic Empty Bottle) and food from tons of local vendors, West Fest is basically a less-congested, more laid-back version of another highly publicized Chicago summer staple. But, there’s one notable difference – and forgive me in advance for sounding like a cheesy realtor – location, location, location. Instead of being in some remote park 10 miles from civilization, West Fest is nestled in the hottest part of town, right between Damen and Wood on Chicago Ave.

Sheffield Garden Walk & Festival July 21-22

Lincoln Park 

An undeniable “adult” version of everyone’s favorite college day-drinking events, the Sheffield Garden Walk take the typical street festival down a notch, trading tents and overpriced snacks for people’s yards, patios and homes. It’s technically a home-tour/festival hybrid, but hey, we Chicagoans will take any excuse to sip early-morning mimosas (or shotgun beers before noon), meet other garden-walkers, and feign an overall air of classiness whenever possible.

North Coast Music Fest August 30-September 1

Union Park

Always a great way to end the summer, North Coast has provided the people of Chicago with awesome acts like Dan Deacon, Knife Party and Yelawolf, as well as sets from DJs like Axwell and Alesso – so whether you’re looking to chill with your significant other or fist-pump the night away with a thousand of your closest friends and neighbors, you can be pretty certain that North Coast has something for you.