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May 2020 events calendar for Chicago

The arrival of May 2020 events in Chicago means summer's just around the corner. Find things to do, festivals and more.

Neal O'Bryan
By Emma Krupp |

Chicagoans come alive again once May rolls around, shaking off the winter doldrums and exploring the city as the days get longer and warmer. You can make the most of spring sunshine by relaxing at a number of newly-opened rooftop bars in Chicago or sampling brews at the string of Chicago beer festivals happening this month. Lovers of the outdoors will also want to spend time in Chicago's best parks, one of which is hosting a kite festival for kids. On days when the weather still feels a little more like winter (because it's Chicago, there are certain to be a few), check out indoor attractions like an affordable art fair at the Chicago Board of Trade or the Art Institute's Monet exhibition. Regardless of what the forecast may throw at us this month, you won't want to miss the best things to do in May.

RECOMMENDED: Our complete events calendar for Chicago in 2020

Featured events in May 2020
Photograph: Tessa Marshall
Things to do, Festivals

Kids and Kites Festival

Cricket Hill, Uptown

Dust off your kite and hope for a steady (but not too strong) breeze! A spring spectacle like no other, this family-friendly tradition gathers hundreds of people at Lincoln Park's Cricket Hill to fill the sky with their colorful flying creations. Bring your own kite or arrive early to build and decorate one.

Things to do, Festivals

Food Truck Social at Lincoln Park Zoo

Lincoln Park Zoo | Chicago, IL, Lincoln Park

If you don’t work in the Loop, your opportunities to eat food-truck cuisine are limited, which is why events like this Lincoln Park Zoo bash exist. Ten dollars gets you entry into the fest, where you can spend an evening listening to live music and sampling dishes from the likes of the Fat Shallot, Aztec Dave’s and Yum Dum.

Chicago Beer Classic
Photograph: Courtesy Chicago Beer Classic
Things to do, Festivals

Chicago Beer Classic

Soldier Field | Chicago, IL, Museum Campus

Ever wanted to stomp around on Soldier Field’s grass? Now you can—and with a beer in your hand! The summer kick-off event always features a respectable roster of local and imported breweries as well as a handful of food-truck vendors and party games spread across two tasting sessions. Attendees receive 48 two-ounce samples, as well as access to exclusive beers, activities and interactive learning opportunities to get better educated about the beer-making process. 

Beer Under Glass, held at the Garfield Park Conservatory, kicked off 2015 Chicago Craft Beer Week.
Photograph: Max Herman
Things to do, Festivals

Beer Under Glass

Garfield Park Conservatory | Chicago, IL, East Garfield Park

Illinois Craft Beer Week kicks off with this annual event at Garfield Park Conservatory, where you can sample some of the finest ales and lagers from local and national breweries amid a sea of foliage. If you're trying to narrow down your list of Craft Beer Week events, this is a good place to separate the worthwhile breweries from the ones you'll save for your next trip to Binny's. Tickets include samples from each of the brewers in attendance and access to grub from local food trucks.

Photograph: Jessica Lynn Capron
Things to do, Festivals


Begyle Brewing Company, North Center

Ravenswood Corridor neighbors Dovetail and Begyle team up for an old-fashioned block party over Memorial Day weekend, complete with live music, food-truck eats and lots of locally brewed beer. Sip a lager from Dovetail or something hoppy brewed by Begyle—all proceeds benefit the Friendship Center, a local food pantry.

Things to do

Memorial Day Parade

Daley Plaza, Loop

After the pigeons are shooed away and a wreath is laid at the eternal flame in Daley Plaza in rememberence of those who have made the ultimate sacrifice for our country, Chicago's annual Memorial Day Parade marches down State Street, from Lake to Van Buren. Crowds line the street, waving flags and paying their respects to members of our armed services as part of this Chicago tradition, which dates all the way back to 1870.

Photograph: Courtesy Star Events
Things to do, Festivals


Armitage and Sheffield Aves, Lincoln Park

Moving from Lakeview to its new home in Lincoln Park this year, Mayfest throws a street party over Memorial Day weekend that’s outfitted with the usual selection of local vendors, tasty food, cover bands and ice-cold beverages.

Things to do, Cultural centers

“Monet and Chicago”

Art Institute of Chicago | Chicago, IL, Grant Park

The Art Institute of Chicago hosted Claude Monet’s debut U.S. solo show in 1895 and was the first American museum to buy one of his paintings. This exhibit acts as an homage to Chicago’s special connection to the “father of Impressionism,” offering a mixture of major works as well as rarely seen sketches and landscapes sourced from local collections.

Music, Classical and opera

Chicago Gospel Music Festival

Various venues, Loop

Now in its 35th year, this fest features a headlining set from Grammy-winning gospel artist (and Kayne West collaborator) Kirk Franklin at Millennium Park, plus a series of performances by local choirs and artists at venues on Chicago’s South and West Sides.

The Other Art Fair
Photograph: Courtesy The Other Art Fair
Art, Fairs

The Other Art Fair

Chicago Board of Trade Building, Loop

A curated group of 120 emerging artists presents their work on the former agricultural trading floor at the Chicago Board of Trade. The pieces start at $150, making this a relatively affordable place to start your art collection and turn the walls of your apartment into a miniature gallery.

Concerts in May 2020

Photograph: Jaclyn Rivas
Music, Music festivals

Chicago House Music Festival

Multiple venues

The city that gave the world house music throws a gigantic celebration every summer, gathering in Millennium Park for a daylong dance party overseen by some of Chicago's top DJs. This year, DJ and producer Steve “Silk” Hurley will headline a concert on Saturday, May 23, capping off an evening that will also feature the presentation of the Chicago House Music Award to local collective The Chosen Few DJs. On Thursday, May 21, and Friday, May 22, fans will be able to attend a series of panel discussions that explore the culture and business of house music.

Tame Impala
Photograph: Jaclyn Rivas
Music, Rock and indie

Tame Impala + Perfume Genius

United Center | Chicago, IL, United Center

Kevin Parker sees himself as a pop producer, collaborating with the likes of Kanye West and Lady Gaga while creating his own extremely popular music under the name Tame Impala. His latest album, The Slow Rush, is more of the same—but in a good way. Pulsing beats, swirling synths and undulating basslines populate Parker's psych-pop soundscapes, which are somehow equally appropriate for late night toking and dentist waiting rooms. If Tame Impala's previous festival apperances are any indication, you can expect lots of fog, trippy visuals and plenty of lasers at this arena performance, which features an opening set from singer-songwriter Perfume Genius.

GYG Chicago TTD