WICKER PARK FEST
July 26 – 28
Three days and dozens of bands make this neighborhood street party one of Chicago’s most anticipated shindigs, with a mix of art, music, and fashion that taps into the city’s creative core. There’s even a festival-within-a-festival for the young attendees. Kids Fest at Wicker Park Fest has child-friendly performers, face painting, games, and quirky activities to rival the action on the main stage. wickerparkbucktown.com
FIESTA DEL SOL
July 27 – 30
Family-friendly entertainment, local art, and carnival rides are a yearly celebration of the Midwest’s vibrant Latino communities, and more than a million visitors show up for the party. You might need all four days to eat your way through the eight-block-long festival, where culinary highlights go from tacos to tostadas. Plan your festival strategy from the fiesta’s classic Ferris wheel, where you can get a birds’-eye view of the boisterous fun happening at street level.
August 1 – 4
Chicago’s biggest music festival turns Grant Park into an open-air performance space, with bucket-list headliners to bring in huge
crowds. The 2019 lineup includes Childish Gambino, Ariana Grande, the Chainsmokers, J Balvin, and the Strokes, but the music doesn’t stop at the big names. More than 170 performers are plugging in for Lollapalooza this year, from country favorites to DJs, while some of Chicago’s hottest venues host after shows that rock into the early hours.
BUD BILLIKIN PARADE AND PICNIC
August 1 – 4
The largest and longest-running African-American parade in America fêtes 90 years of music, oats, and fun this summer, and the 2019 celebration is going to be big. A two-mile parade route winds from Bronzeville to Dr. Martin Luther King Jr. Drive, with performance teams that have spent all year perfecting crisp moves and stylish duds. Marching bands, cheer, dance, and drill teams come from around the country to compete for top honors.
NORTHALSTED MARKET DAYS
August 10 – 11
A half mile of arts, crafts, food, drinks, and community spirit, this open- air shindig is the biggest street festival in the Midwest. It cuts a colorful swath through Chicago’s historic Boystown neighborhood — the first- ever designated gay village in the United States — but Northalsted Market days welcomes all. Four stages feature a long list of musical acts who help make this a neighborhood event with global reach.
AIR & WATER SHOW
August 17 – 18
Daredevil pilots take to the sky above Lake Michigan for a heart- stopping two-day program that brings big crowds to the waterfront. Stars of the show include flyers from U.S. Navy’s Blue Angels and
the Royal Air Force Red Arrows, an aerobatic team from the United Kingdom known for spectacular feats in tight formation. In-the-know spectators come early to North Avenue Beach, staking out a prime spot for a day of plane-spotting in the summer sunshine.
CHICAGO JAZZ FESTIVAL
August 23 – September 1
Syncopated rhythms ll Millennium Park with finger-snapping grooves at a festival that draws together great Chicago musicians and international names — the 2019 headliners include vocalist Cécile McLorin Salvant and the globe-hopping Eddie Palmieri Sextet. The music doesn’t stop at Pritzker Pavilion, either. Chicago stays jazzed up with after-hours shows at theaters and jazz clubs across the city, where you might spot big-name musicians nodding along with the crowd.
NORTH COAST AT NORTHERLY ISLAND
August 30 – 31
A new location on Northerly Island means blissful breezes to cool down crowds at this electronic dance music festival, where energetic performances keep attendees dancing until well after dark. This year’s big names include Bassnectar and Major Lazer, while more than 20 acts will keep two stages thrumming for the two-day event. After a long season of music, North Coast at Northerly Island is billed as “Summer’s Last Stand,” and artists deliver with career-making sets.