With August in full swing, a reluctant countdown to fall has begun—but the season’s fast-approaching end certainly hasn’t encouraged Chicagoans to slow down. The opposite: from music festivals to rooftop soirees, the city’s social calendar is spilling over with can’t-miss events to fill the remaining warm-weather days.
Back for the 59th year, the city’s longest-running free show of its kind continues to soar above expectations. U.S. Navy Blue Angels, U.S. Army Parachute Team Golden Knights, and U.S. Navy Parachute Team Leap Frogs will take center sky with serious gravity-defying stunts, simulated water rescues, and parachute drops from 12,500-feet. August 19-20, 10 am – 3pm. Viewable on lakefront from Fullerton Ave. to Oak St.
After a season of culturally enriching Millennium Park concerts, catch indie-rock duo—and Chicago natives—Wild Belle, as well as singer/songwriter Sam Trump with 6-piece ensemble Acoustive Audile, as they take the Jay Pritzker Pavilion stage to close out Chicago’s favorite (and free!) summer music series. August 21, 6:30 pm. 201 E. Randolph St.
For the first time in over 90 years, a near-total solar eclipse will hit the Chicago sky. Slated for an 11:54 am appearance, this once-in-a-lifetime spectacle is the perfect excuse to sneak out of the office for a mid-day Monday break. IO Godfrey invites guests to sip on frozen, color-changing Eclipse-themed cocktails while watching the real thing. August 21, 11 am – 4pm. 127 W. Huron St
Prep yourself (and your stomach) for the return of Logan Square’s second annual Food Truck Social. The three-day foodie affair brings more than 25 of the city’s favorite mobile eats to one of Chicago’s trendiest dining districts. Crack open a cold Revolution brew, kick back to live music, and pig out on Chicago’s finest “truck fare.” August 25, 5 pm – 10 pm, August 26-27, 11 am – 10 pm. Humboldt Blvd. between Armitage Ave. & Bloomingdale.
This year’s North Coast Music Festival is sure to hit high notes when hip-hop superstar Gucci Mane, reggae royalty Damien “Jr. Gong” Marley, and more A-list acts take the stage for "summer's last stand." Hosted in Union Park over Labor Day weekend, the star-studded affair helps wind down festival season in boisterous style. September 1–3. 1501 W. Randolph St.
Whether you’re a red, white, or rosé connoisseur, the Windy City Wine Festival is a surefire way to beat the end-of-season blues. Hosted at Buckingham Fountain, the two-day event boasts local eats from leading Chicago restaurants, along with seminars, cooking demonstrations, and tastings that will undoubtedly boost your spirits. September 8, 5 pm – 10 pm., September 9, 3 pm – 8 pm. 301 S. Columbus Dr.
Every Wednesday through the September 13, the Shedd Aquarium’s 32,000 aquatic residents share the spotlight with the city’s best jazz performers. Each week, the Lakeside Terrace welcomes a new live act for guests to enjoy as they explore the exhibits and sip on a cocktail. Wednesdays through September 13, 5 pm. 1200 S. Lake Shore Dr.
Before cooler temperatures settle in, get a few last outdoor workouts in at the Park at Wrigley’s workout series. Whether you’re down for a CrossTown Fitness-led session or are looking to balance out with Bloom Yoga, these exclusive mornings at the Park are dedicated to keeping you fit and fresh. Wednesday and Thursdays through October 26, 7 am. 3637 N. Clark St.