10 Summer-Worthy Events Happening This August in Chicago

By Urbanmatter Chicago @UMatterChicago

Get Your Kicks While You Still Can

How can it already be August? Chicagoans know that summer flies by, and it’s important to make the most of it.

Since August is typically thought of as summer’s last ‘hoorah,’ we pulled together a list of the best events happening this month so you can live it up this summer before it’s gone. So get out there!

Chicago Hot Dog Fest

Photo Credit: Life in Leggings

You can’t get more Chicago than this. Join other hot dog lovers from August 5 – 7 at Stockton and LaSalle to enjoy tasty different ‘dawg’ varieties.

Retro on Roscoe

Photo Credit: Clip Art Kid

Head over to Roscoe Village from August 12 – 14 to check out their annual vintage-inspired celebration, Retro on Roscoe. It’s the best family event that the city has to offer.

Northalsted Market Days

Photo Credit: Northalsted Business Alliance

Believe it or not, this Boystown event is the largest outdoor street festival in the Midwest! Visit the neighborhood from August 13 – 14 and enjoy a summer celebration that has all the necessities: food, drinks, music, and fun.

Brooklyn Brewery Mash

Photo Credit: Brooklyn Brewery

In a New York state of mind? You’re in luck because Brooklyn Brewery is embarking on a national tour and the Windy City’s their next stop. Check out four days worth of beer, music, food, and cultural immersions from August 11 – 14.

Reggae Fest

Photo Credit: Reggae Fest Chicago

Don’t worry, be happy. We think that’s a perfect mantra for summertime. Chill to the feel-good vibes of reggae music from a lineup of 11 artists in Addams Medill Park on August 13.

Festa Italiana

Photo Credit: Chicago Now

Pasta, pizza, meatballs – keep ’em comin’! From August 18 – 21, enjoy authentically delicious samples of your favorite hearty Italian eats at this cultural event in Little Italy on historic Taylor Street, with music, dancing, and more.

Chicago Air & Water Show

Photo Credit: Youtube

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, grab a perfect viewing spot at North Avenue Beach.

Taste of Greektown

Photo Credit: FSR Magazine

From August 27 – 28, 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!

Bucktown Arts Fest

Photo Credit: Timeout

This creative neighborhood is hosting a nonprofit event from August 27 – 28 that supports local artists, artists in residence, and art programs at local schools. Stop here to admire the talent of others and pick up a new decorative item for your place.

Motor Row Craft Beer & Wine Fest

Photo Credit: The Chef’s Connection

Beer and wine. Need we say more? Aside from displays of impressive automobiles and live music, enjoy all the craft cocktails, wine, and brews that your heart desires at this fest on Michigan Avenue between Cermak and 24th, from August 27 – 28.

How do you like to spend your last weeks of summer? Tell us below!