Chicago Food, Festivals and Family Fun for Labor Day! - Checkexpress

Chicago Food, Festivals and Family Fun for August!

Summer flies FAST when you’re having fun! Chicagoans know how to enjoy the sunshine in the city before the chill of fall and snowy winters. August is thought of as summer’s last month of celebration before brisk air fills the street and the leaves begin to change. Checkexpress wants you to enjoy as many festivals and fun before the Chicago winds breeze through and shift the weather. Check out these end of summer activities & create more best of summer 2019 memories while there are plenty of opportunities!
Chicago Food, Festivals and Family Fun for Labor Day! - Checkexpress


Renaissance Fair
August 3 – September 2

Watch knights joust, shop in an artisan market, mingle with costumed minstrels, play games, and attend shows at Bristol Renaissance Faire in 16th century England (also known as Kenosha, WI). Open weekends and Labor Day, September 2, 2019.

Chicago Jazz Festival 
August 23 – September 9 
Free Admission 

The oldest of Chicago’s free lakefront music festivals boasts an incredibly diverse lineup during its carefully curated 10 days, which includes free neighborhood concerts leading up to the main show at Millennium Park. The range of artists comprising the Chicago Jazz Festival runs the gamut from jazz legends to influential modern masters and crucial new voices in the genre’s continuing evolution.

An all-ages, multi-venue music event, the Chicago Jazz Festival brings free jazz to downtown’s beautiful Millennium Park, as well as inside the nearby Chicago Cultural Center.

North Coast Music Festival 
August 30 – August 31

The North Coast Music Festival brings an array of electronic artists to Chicago’s Northerly Island. This year’s headliners include Bassnectar, Major Lazer, and Flux Pavilion.


Great American Lobster Fest 
August 30 – September 1

The Great American Lobster Fest is the Midwest’s largest Lobster and Seafood Festival. We’re returning to Chicago’s legendary Navy Pier on Labor Day Weekend to celebrate Summer’s Last Hurrah! Enjoy live lobster flown in fresh from the cold waters of the East Coast courtesy of our official seafood provider, Lobster Gram, live music performances, family-friendly games and activities, unique arts/craft shopping, land food options, and cold beverages.

Chicago Food, Festivals and Family Fun for Labor Day! - Checkexpress

And, even more family fun! 

Chicago Air & Water Show
August 17 – August 18 
Free Admission 

Chicago Air & Water Show features daredevil pilots, parachute teams, jets flying in formation, an air/sea rescue demonstration, and military airplanes. Watch it from the waterfront near North Avenue Beach.

Figures of Speed
Now through September 22 at the Museum of Contemporary Art 

This is the first ever exhibit dedicated to the work of Virgil Abloh, a multimedia, multi-genre artist, architect, DJ, and Chicago native. He was Kanye West’s top creative collaborator, designing album covers and merchandise, and he started his own fashion brand Off-White. His trajectory continues, though: Last year, he was named Men’s Artistic Director of Louis Vuitton. The exhibition covers the many aspects of his multi-disciplinary career and how they intersect.

Visit Choose Chicago for more events happening in Chicago for Labor Day 2019! Or, visit Events12 for even more family fun ideas for August! 


What we can do to help you prepare for a fun day…

Prepaid Debit Cards

No need to carry around dollar bills and loose change, which you may lose in the crowded festivals and concerts. A prepaid debit card will act as your cash, so you may spend as much or as little as you wish. Plus if your teens want to go out with their friends, you can set an appropriate spending limit.

Check Cashing

If you’d prefer using cash for your activities and purchases, then we have the perfect option for you! We have nine locations throughout Chicagoland. Use your phone to easily find one of our currency exchanges so you can cash your check quickly and be on your way to the fun.