There seems to always be something to do in Chicago: from St. Patrick’s Day festivities to secret speakeasies, the Windy City has some of the coolest activities in the Midwest. But this spring, a few events stick out among the rest, and they’re taking the city by storm. Check out these Chicago events this May and celebrate the warm months the right way.
Chicago Beer Classic
Date: Saturday, May 5th
Cost: $65-GA; $95-VIP
Boasting beer samples from more than 75 breweries, the Chicago Beer Classic is not one to miss this spring. Along with many local breweries, this event brings other beer brewers from across the country to serve up pints to thirsty festival-goers on Soldier Field. General admission for the first or second session (11:30am-2:30pm or 4:30pm-7:30pm) includes 48 two-ounce samples, a souvenir tasting glass, and games and activities. Or, if you feel like ballin’ out, spend $30 more on VIP tickets and add an additional half hour of tasting plus 12 extra beer samples, exclusive seating, giveaways, and more.
Chicago Zine Fest
Date: May 18th – May 19th
Cost: Free!

Are you into illustrations or zines? Want to learn about publishing? The Chicago Zine Fest is the perfect event for you. Celebrating small press and independent publishers, this festival takes place annually and offers workshops, guest speakers, and exhibitors. Learn from some of the most talented illustrators, photographers, and artists as they showcase their work and talk about what it’s like to work in the Zine world. Catch this year’s festival and don’t worry about bringing your wallet; everything about this event is free!
Mayfest
Date: May 18th – May 20th
Cost: $10
Grab that spare $10 bill lying around and head to Mayfest where it will get you admission to this awesome festival. Celebrating its 23rd year, Mayfest takes place annually in the Lakeview neighborhood and provides Chicago residents with some of the best local music, food, and entertainment the city has to offer. Check out the beer garden before watching a local band showcase its talent.
Kids and Kites Festival
Date: May 5th, 10am-4pm
Cost: Free!
This one’s for the whole family. Enjoy a day on Cricket Hill in Lincoln Park where, in conjunction with Chicago’s Year of Creative Youth, the city will be handing out free kite kits (while supplies last!) to children so they can create their very own kites to fly. Kids and adults can also check out the professional kite flyers and their eclectic contraptions, plus face painting stations, balloon artists, and crafts for sale. Admission is free to this family-friendly event, and there’s no better way to celebrate spring’s arrival than by playing outdoors all day.
Night Nation Run
Date: May 19th
Cost: $30 early bird, $60 full price

Coined the World’s 1st Running Music Festival, this 5K fun-run comes to Chicago on May 19th. Rally some friends to join you at Soldier Field where you’ll enjoy a pre-party, replete with a DJ and dancing. The run will go in heats, and the course is filled with party zones, light shows, and DJs bumping music along the way. Once you’ve crossed the finish line, live music on the main stage, confetti, and fog machines will get the crowd pumped up for the surprise headliner DJ make an entrance.
Bike the Drive
Date: Sunday, May 27th; 5:30am-10:15am
Cost: $17-$66

Have you ever wanted to bike freely down Lake Shore Drive without all the traffic? This is your chance! The annual Bike the Drive shuts down the iconic Lake Shore Drive for nearly 5 hours while a 30-mile ride ensues. Open to all skill levels, Bike the Drive’s proceeds benefit Active Transportation Alliance whose mission is to be Chicago’s voice for better biking and walking transit. Live out your biking dreams at this event, and know that your money is going towards a great non-profit.
Lincoln Park Wine Fest
Date: May 18th – May 20th, times vary
Cost: $40-$85
Spread out over the 2-acres of beautiful Lincoln Park, this festival draws a huge crowd every year, and this year will be no exception. This year, Friday’s session will focus exclusively on rosé and sparkling wines, while Saturday and Sunday will feature more than 90 varieties of wines. Grab your tickets and receive 12 tastings with admission. Enjoy live entertainment, music, food and wine pairings, and local artists. Learn about the different wines from expert sommeliers and brand ambassadors while you sip on some tasty vino.
Chicago is calling! Whether you’re looking for a new place or are thinking of moving there in time for these spring events, check out our Chicago apartments for rent and find one that’s right for you.
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