Best Outdoor Festivals in Chicago You Can’t Miss

The numerous Chicago festivals are the city’s way of making the most out of the warm summer weather before it plunges back into the harsh Chicago winter. Here’s a list of some of the more popular outdoor festivals in Chicago.

Taste of Chicago

The granddaddy of outdoor festivals, Taste of Chicago is Chicago’s biggest event. Having started out as a modest one day festival in 1980, Taste of Chicago has blossomed into one of the world’s largest outdoor food festivals attracting over 3 million people each year lining up to scarf down deep dish pizza and giant BBQ turkey legs.

Chicago Blues Festival

Over a half million music fans turn out each year for the Chicago Blues Festival in this “Blues Capital of the World.” The festival attracts performers ranging from seasoned blues men to promising up-and-comers.

Chicago Jazz Festival

Jazz aficionados mark Labor Day weekend on their calendars each year so they don’t miss the Chicago Jazz Festival in Grant and Millennium Parks, which plays host to some of the world’s greatest jazz artists. The Chicago Jazz Fest also holds the distinction of being the city’s longest running music festival.

Lollapalooza

The traveling music festival organized by Jane’s Addiction singer Perry Farrell started in 1991 and has grown into one of the world’s largest—and most annually anticipated—live music events. Lollapalooza takes place in Chicago’s Grant Park during the last weekend of July. It consists of several stages, including one for children and a main stage, plus Chowtown (where restaurant vendors reside), a retail component and more.

In previous years, the festival occurred for three days. There will be 170 bands, which consist of major headliners, up-and-coming acts, and deejays. The festival has hosted the likes of Lady Gaga, Sam Smith, A Tribe Called Quest, Beastie Boys, The Black Crowes, Metallica, and Kanye West on the main stage.

Chicago Gourmet

Chicago Gourmet in Millennium Park celebrates the city’s vibrant culinary scene. For one flat (albeit pricey) fee, guests can sample various cuisines prepared by some of Chicago’s top chefs, watch numerous cooking demonstrations, and taste wine and spirit samples from over 300 wineries and 65 spirits producers.

Chicago Ginza Holiday Festival

The annual Ginza Holiday festival, presented by the Midwest Buddhist Temple, is a celebration of Japanese culture, featuring master craftsmen from Tokyo demonstrating their skills learned over generations. The crafts, along with other Japanese merchandise, are offered for sale. Beyond the demonstrations and sale, children will especially enjoy performances of taiko drumming and martial arts demonstrations. Plenty of Japanese cuisine and beer are available as well.

Kids & Kites Festival

Venture up north to picturesque Montrose Harbor along Lake Michigan for the annual Kids and Kites Festival, a day of fun and sun where the city provides materials for children to make and fly their own kites. Moreover, there are demonstrations by expert kite makers featuring amazing “large form” kites. Those not satisfied with the basic diamond-shaped kite can peruse the fancier kites available for sale. Food vendors will also be on hand to delight festivalgoers.

Chicago World Music Festival

The Chicago Department of Cultural Affairs started the Chicago World Music Festival in 1999 with the goal of celebrating the diverse music of cultures around the world, hosting a week-long festival each September. Instead of harboring the music all in one location, the DCA spreads events throughout the city, hosting performances at some of the city’s museums, cultural centers, parks, and music clubs, with most events being free or charging a very low ticket price.

Chicago Pride Fest

Dubbed the “first official party of summer,” the two-day Chicago Pride Fest, held the Friday and Saturday before the annual Chicago Pride Parade, packs the revelers in along North Halsted Street who come for the celebration, food, live entertainment, and scores of vendors selling arts and crafts.