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May Chicago festival calendar

Hit the streets with the family for ribs, music, culture and more at these top Chicago summer festivals
Photograph: Maddie Blecha Do Division - June 2, 2013
By Time Out Chicago staff, compiled by Zach Long |
Traditionally, May marks the arrival of summer in Chicago, bringing sun and outdoor events to the city's streets. If you're not outside enjoying a meal at a patio or garden, you're watching some bands play at a music festival or persuing some local art at a craft fair. May is one of those months that makes us truly glad that we live in Chicago. If you're still looking for an excuse to get out of the house, you should check out our list of the best Chicago festivals that are happening this month.
Things to do, Festivals

Chicago International Movies and Music Festival

In its sixth year, CIMMfest is a sprawling affair spread across the city—venues include the Metro, Concord, Double Door, City Winery, the Logan, Subterranean, Hideout, Empty Bottle, Concord, Lincoln Hall, LSA and more. With dozens of music-centric films and live bands, it can be a task to navigate, so we'll cut to the highlights. Yo La Tengo headlines the first night, neo-disco act Escort the second. Italian psych legend Goblin plays its score to the classic horror flick Suspiria at Metro on May 3. Nineties rock dudes Jimmy Chamberlain (Smashing Pumpkins) and Scott Lucas (Local H) team to provide a live score to Sergei Eisenstein’s pioneering silent protest film Battleship Potemkin (No, really).

Things to do, Quirky events


icon-location-pin Various locations throughout Chicago,

The newest series of events presented by Chicago Loop Alliance transforms mundane, downtown alleys into glowing laser light shows. Each month, the party will move to a different alley in the city, transforming the space for a single evening. The inaugural event in the Sullivan Center alley will feature immersive art from Johalla Projects, a Zipcar DJ booth and a cash bar.


Found Footage Festival

Featuring VHS finds from garage sales, thrift shops and dumpsters, curators Joe Pickett  and Nick Prueher provide live commentary as they present their unearthed oddities. This year's festival includes an instructional video titled "How to Have Cybersex on the Internet and video for dog breeders detailing the process of "whelping."

Things to do, Festivals

Cinco De Mayo Festival

Yes, it takes place on the Dos, Tres and Cuatro of Mayo, but no Cinco celebration is more authentic than the fete in Little Village. The kiddies can ride live ponies and carnival attractions, and there's food, arts, crafts and music in this massive celebration of Mexican culture in the Midwest.

Things to do, Festivals

Kids and Kites Festival

Celebrate the arrival of spring at this free, outdoor family-friendly festival at Cricket Hill in Lincoln Park where kids can fly a kite or watch professional demonstrations. Free paper kites will be provided, but families will also be able to purchase more intricate flying creations from a variety of vendors.

Things to do, Festivals

Derby Days Street Festival

If you can't make it out to Chruchhill Downs for the big race this year, just head to Joe's Bar on Weed Street. The bar will be shutting down the street, setting up a jumbotron and serving up Mint Juleps to thirsty attendees. Pick your favorite, place your bets (the bar offers off-track betting, for a $2 fee) and get ready to experience in the Kentucky Derby in the streets of Chicago.

Things to do, Festivals

Polish Constitution Day Parade

The Polish Constitution was signed on May 3rd, 1791 and for the past 123 years Chicago has celebrated the date with a parade in Grant Park. Over 250,000 attendees flock to Columbus Drive to watch the procession and honor Europe's first democratic constitution.

Shopping, Arts, crafts & hobbies

Revolution Craft Show

Peruse arts and crafts from more than 40 Midwest artisans, enjoy live music and refuel with snacks from food trucks in Salvage One's vintage-decorated space.

Things to do, Festivals

Cinco De Mayo Parade

Although most Americans use Cinco De Mayo as an excuse to drink margaritas, the holiday actually commemorates the victory the Mexican forces had over the invading French army on 5 May, 1862. This annual celebration in Pilsen fills the streets with colorful attire and traditional music. The parade starts at Cermak and Wood and travels west to Kedzie.

Things to do, Festivals

Studs Terkel Festival: "Let's Get Working"

The University of Chicago celebrates the life and work of Studs Terkel, a famous writer, broadcaster and activist who won a Pulitzer Prize. Terkel passed away in 2008, but his work has inspired a new generation of socially conscious journalists, including featured speakers like This American Life host Ira Glass and The Interrupters producer Alex Kotlowitz. You'll find a complete list of events at the festival website.

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