14 Summer-Worthy Events Happening in Chicago This August

How can it already be August? Chicagoans know that summer flies by until we’re doomed to a grueling 7-month winter. And, since August is typically thought of as summer’s last ‘hoorah’ before September changes Chicago’s colors, we pulled together a list of the best events happening this month, so you can live it up before the warmth is gone.

Get out there and make the most of summer ’19 while you still can!


These are the best August events happening in Chicago!


Photo Credit: Lollapalooza Facebook

August 1 – 4 @ Grant Park


Chicago’s most popular music festival phenomenon returns for another four days this year, with headliners such as The Strokes, The Chainsmokers, Childish Gambino, Tame Impala, Twenty One Pilots, Ariana Grande, Flume, and more. Check out lineup and aftershows info here. And make sure to steer clear of these people.


Photo Credit: EdgeFest

August 3 – 4 @ Broadway from Thorndale to Ardmore


An annual event that is perfect for family, friends, and even pets, this neighborhood street fest has all the essentials – food, drinks, local retail vendors, and live music. Don’t miss the best of Edgewater all in one spot!

Chicago Hot Dog Fest

august in chicago
Photo Credit: Life in Leggings

August 9 – 11 @ Lincoln Park at Stockton & LaSalle


You can’t get more Chicago than this. Join other hot dog lovers at Stockton and LaSalle to enjoy tasty ‘dawg’ varieties.

Retro on Roscoe

Retro Cars
Photo Credit: Clip Art

August 9 – 11 @ 2000 W Roscoe St


Head over to Roscoe Village to check out their annual vintage-inspired celebration, Retro on Roscoe. It’s the best family event that the city has to offer and you’re bound to find yourself starstruck by all the classic cars on display.

Bud Billiken Parade

august in chicago
Photo Credit: Bud Billiken Parade

August 10 @ S Martin Luther King Drive


The oldest and largest African American parade in the nation returns to Chicago to honor hometown heroes and celebrate the talented youth community. Speaking of hometown heroes, one of our previous Grand Marshal was none other than Chance the Rapper, so you never know who you’re going to find at this popular event.

Northalsted Market Days

august in chicago
Photo Credit: Northalsted Business Alliance

August 10 – 11 @ North Halsted St from Belmont to Addison


Believe it or not, this Boystown event is the largest outdoor street festival in the Midwest! Visit the neighborhood to enjoy a summer celebration that has all the necessities: food, drinks, music, and fun.

Chicago Air & Water Show

august in chicago
Photo Credit: Youtube

August 17 – 19 @ North Avenue Beach

When people think of Chicago summers, the Air & Water Show is usually one of the first things that comes to mind. Don’t miss the spectacle that wows us year after year, and grab a perfect viewing spot at North Avenue Beach.

Wizard World Comic Con

august in chicago
Photo Credit: Wizard World

August 22 – 25 @ Donald E. Stephens Convention Center

Head to this iconic convention for graphic novels, gaming, cosplay, and pop culture featuring seminars, panels, and special guests. This year’s celebrities include Aquaman‘s Jason Momoa and Gotham‘s Ben McKenzie. The full schedule has yet to be released this year!

Taste of Greektown

august in chicago
Photo Credit: FSR Magazine

August 23 – 25 @ 400 S Halsted St & Van Buren

Celebrate Mediterranean flavors from the restaurants that line the streets of Greektown, right near the West Loop, in this cultural event that also features music and entertainment. Opa!

Chicago Jazz Festival

labor day weekend in chicago

August 23 – September 1 @ Various Venues

The Chicago Jazz Festival promotes appreciation for jazz through live music performances. They combine the city’s jazz talent with national and international artists to entertain and educate audiences. And it’s free!

Lagunitas Beer Circus

Photo Credit: Lagunitas Beer Circus Facebook

August 24 @ Douglas Park

Get weird at the most unusual circus you’ve ever attended! Taste the sweet, summery aftertaste of Lagunitas beer as you watch trapeze artists, daredevils, strongmen, and some even stranger still perform bodacious acts on stage at Douglas Park.

Bucktown Arts Fest

august in chicago
Photo Credit: Timeout

August 24 – 25 @ Senior Citizens Memorial Playlot Park

This creative neighborhood is hosting a nonprofit event that supports local artists, artists in residence, and art programs at local schools. Stop here to admire the talents of others and pick up a new decorative item for your home.

North Coast Music Festival

labor day weekend in chicago
Photo Credit: North Coast Festival

August 30 – 31 @ Huntington Bank Pavillion

The 2019 North Coast Music Festival features headliners that include Bassnectar, Major Lazer, and Flux Pavillion. From EDM to indie rock, there’s music for everyone to enjoy. Weekend, single-day, and VIP tickets are still available for purchase!

Taste of Polonia Festival

september events
Photo Credit: Copernicus Center

August 30—September 2

Celebrate Chicago’s renowned Polish culture at this outdoor festival near the Copernicus Center featuring delicious Polish eats, live music, Polka dancing, carnival rides, and craft vendors.


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