Travel Magazine

10 Things to Do in Chicago This May

By Urbanmatter Chicago @UMatterChicago

We’ve got a pretty serious case of spring fever now that May has arrived. Luckily, this is the time of year when the city of Chicago really starts ramping up for the best outdoor events. Here’s the best of what’s happening this month:

Chicago Beer Classic

may events chicago

Photo Credit: Chicago Beer Classic

May 6

Head to Soldier Field to enjoy endless samples of craft beer from breweries like Half Acre, Pollyanna Brewing Company, Abita, Brooklyn Brewery, and tons more. Tickets are selling fast, get a general admission ticket for $65.

Kids & Kites Festival

may events chicago

May 6

The perfect spring event for families invites you to Cricket Hill in Lincoln Park for a day of kite flying. Don’t have a kite? You can build your own during the event. The best part is admission is free!

Cinco de Mayo Parade

may events chicago

Photo Credit: The DePaulia

May 7

Kicking off at noon on Cermak and Damen, enjoy a festive parade in Little Village with live music, arts and crafts, and food and beverage that celebrates Mexican culture.

Lincoln Park Zoo Food Truck Social

may events chicago

Photo Credit: Todd Rosenberg Photography for Lincoln Park Zoo

May 13

Treat yourself to an after-hours event at the zoo with delicious meals on wheels, such as donuts, tacos, pierogis, and more. The food truck social welcomes all ages from 6:30pm – 9:30pm and entry is $10.


may events chicago

Photo Credit: Raney Images for Mayfest

May 19 – 21

Now in its 22nd year, Mayfest returns to bring live music, delicious food, and a great time to Lakeview. Hang out under the massive big-top tent, grab a drink from the beer garden, and kick back with your friends for only $10.

Night Nation Run

may events chicago

Photo Credit: Night Nation Run

May 20

Join in on the world’s first running music festival storming Soldier Field. This 5k features live EDM music, lights, lasers, an illuminated race course, and a main stage after party with celebrity DJ performers. Early bird tickets are only $29.99.


may events chicago

Photo Credit: Youtube

May 20

Rock out at this one-day music festival at the Hollywood Casino Amphitheatre presented by Chicago’s WKQX, featuring bands like The 1975, Jimmy Eat World, Sum 41, and Warpaint. Tickets are selling now for $25.

Memorial Day Parade

may events chicago

Photo Credit: City of Chicago

May 27

This annual parade honoring fallen men and women of our nation’s armed forces is one of the largest in the country, and is certainly a spectacle all should witness. The wreath-laying ceremony takes place at 11am and the parade begins at noon.

Belmont-Sheffield Music Festival

may events chicago

Photo Credit: Lakeview East Chamber of Commerce

May 27 – 28

Here to welcome the warm weather is one of Chicago’s best neighborhood street fests. From noon to 10pm, enjoy plenty of food, drinks, and live music by tribute bands on Sheffield from Belmont to Roscoe.

Bike the Drive

may events chicago

Photo Credit: Bike the Drive

May 28

The month of May calls for a scenic bike ride down Lake Shore Drive, free of cars! Join others for this event that benefits the Active Transportation Alliance. Ticket prices vary for members and non-members and will increase on the day of event.

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