The Ultimate End of Summer Chicago Bucket List

I know, it’s kind of hard to imagine that summer is already coming to a close, but that time of year has finally arrived. Welcome to the final days of warm weather as we slowly descend into 10 months of winter madness.

As college campus neighborhoods once again overflow with student life and the hottest days gradually cease to exist, you’ve either completely given up hope of planning anything else the rest of the season, or you’re aching to get a few last-minute events in before the warmer months are totally over.


Whatever the case, it’s time to finish off the summer right. Consider this your ultimate, end-of-summer Chicago bucket list.


Photo Credit: Lollapalooza Facebook

August 1-4 @ Grant Park


While this may already be on some of your lists, it’s not too late to purchase a ticket to see some of the best bands of our generation head to Grant Park for this massive extravaganza of a music fest.

Chicago Hot Dog Fest

Hot Dog Fest
Photo Credit: Chicago History Museum Facebook

August 9-11 @ Lincoln Park


Yup, this entire festival is dedicated to the grandeur of the hot dog, specifically celebrating the glorious condiments used on the Chicago dawg. Hot dog vendors from all over the city gather at the corner of Stockton and Lasalle for a day of beefy goodness.

Taco Bar Crawl

Zombie Taco
Photo Credit: Zombie Taco Facebook

August 10 @ River North


Tickets to this tasty crawl include seven delicious tacos, some amazing drink specials, and various prizes during the event. You’ll hit up taco bars like AceBounce, Bar Louie, El Hefe, Hubbard Inn, Ironside, Moe’s Cantina, Old Crow, Taco Joint, Kerryman, Theory, Zombie Taco, Bub City, and more TBD.

Lagunitas Beer Circus

Photo Credit: Lagunitas Beer Circus Facebook

August 24 @ Douglas Park


Yeah, I realize I’ve given you two things to do on the same day, but c’mon, can’t you decide for yourself? This one’s a little more out there—Lagunitas Brewing Company presents a day-long circus performance, complete with samples of their savory brews and all the food you can eat.

Chicago Air and Water Show

Air and Water Show
Photo Credit: Chicago Air and Water Show Facebook

August 17-18 @ North Avenue Beach


One of the most classic events of the year, the Chicago Air and Water Show is always an unbelievable sight. Watch as U.S. fighter pilots take to the skies and showcase their talents to the crowds on North Ave Beach.

North Coast Music Festival

North Coast Music Festival
Photo Credit: North Coast Music Festival Facebook

August 30-31 @ Union Park


With headliners like Bassnectar, Major Lazer, and Flux Pavilion, this year’s North Coast Music Festival is destined for greatness. Make this grand three-day music festival your final goodbye to summer ‘19.

See a Movie in the Park

Millennium Park
Photo Credit: Millennium Park Facebook

Through August 20 @ Various Locations

While you’ve missed the grand majority of them (nice job), there’s still a month and a half left of movies in the park to attend. Catch at least one of them before mid-September for a night to remember.

Chicago Half Marathon

Chicago Half Marathon
Photo Credit: Chicago Half Marathon Facebook

September 29 @ Lake Shore Drive

Whether you’re participating yourself or watching bae shed 20 pounds of pure sweat, the Chicago Half Marathon is an event you have to add to your bucket list. It’s always satisfying both to cross that finish line and to watch others who do.


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Featured Image Credit: Lagunitas Beer Circus