10 Things to Do in Chicago This Mayon March 3, 2020 at 2:30 pm

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 are the best things to do in Chicago this May!

Chicago Beer Classic

may events chicago
Photo Credit: Chicago Beer Classic

May 2 | 12 – 4 pm OR 5 – 9 pm @ Soldier Field

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 $49. VIP tickets are $69 and extend each session by an hour.

Kids & Kites Festival

may events chicago

May 2 | 10 am – 4 pm @ Cricket Hill in Lincoln Park

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 5 | 12 pm @ Cermak Rd. & Damen Ave. to Marshall Blvd.

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 9 | 7:30 – 10 pm @ Lincoln Park Zoo

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. Ticket entry is $10.

Night Nation Run

may events chicago
Photo Credit: Night Nation Run

May 16 | Gates Open 6 pm, Pre-party Begins 7 pm, Race Begins 8:30 pm @ Soldier Field

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 prices are only $29.99. Full registration is $49, so get your tickets as soon as possible!

Memorial Day Parade

may events chicago
Photo Credit: City of Chicago

May 23 | 12 pm @ State St. from Lake St. to Van Buren

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 11 am and the parade begins at noon.

Belmont-Sheffield Music Festival

may events chicago
Photo Credit: Lakeview East Chamber of Commerce

May 23 – 24 | 11 am – 10 pm @ Sheffield from Belmont to Roscoe

Here to welcome the warm weather is one of Chicago’s best neighborhood street fests. From noon to 10 pm, 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 24 | 5:30 – 10 am @ Lake Shore Drive

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. Registration varies for members and non-members and will increase on the day of the event.


may events chicago
Photo Credit: Raney Images for Mayfest

May 29 – 31 | Fri 5 – 10 pm, Sat/Sun 12 – 10 pm @ 1000 W Armitage Ave

By now an annual Chicago tradition, 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.

Do Division

Photo Credit: Do Division Facebook

May 29 – 31 | Fri 5 – 10 pm, Sat/Sun 12 – 10 pm @ Division St. from Damen to Leavitt

This area of West Town is famous for throwing a street fest to kick off summer all along Division Street. Thanks to local vendors providing delicious bites and beer along the way, you can travel from Empty Bottle to Subterranean while shopping independent stores.

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