Can’t Miss May Festivals in and Around Chicago

May is one of the most beautiful months to spend outside in the city.  Skies are blue, everything’s in bloom, and summer is just around the corner.  That means that Chicago is just bursting with all sorts of exciting things to do and see with festival season is in full swing!

So, to better plan your spring activities and make the most of the season, we’ve put together a list of some of the can’t miss may festivals in and around Chicago.  Check it out!

Beer Under Glass

When:  Friday, May 18th

Where:  Garfield Park Conservatory, East Garfield Park

This annual event kicks off Illinois Craft Beer Week in Garfield Park Conservatory.  Come out and sample some of the finest lagers and ales from both local and national breweries under a sea of beautiful foliage.  Of all of the Craft Beer Week events, Beer Under Glass is the festival you won’t want to miss. Tickets include samples from each of the brewers in attendance as well as access to good eats from local food trucks.

Skokie Festival of Cultures

When: Saturday, May 19th – Sunday, May 20th

Where:  Oakton Park, Skokie

Who says you have to leave Chicago to travel the world?  Experience a whirl-wind tour around the world at this popular and free festival in Skokie.  The family-friendly event features ethnic music, dance, food and arts. Event goers can celebrate cultural diversity through all sorts of fun games and activities, including an international beer tasting competition.   

Food Truck Social at Lincoln Park Zoo

When:  Saturday, May 19th

Where:  Lincoln Park Zoo, Lincoln Park

This annual food truck feast at the zoo is every foodie’s dream come true!  Treat yourself to tacos, grilled cheese, pierogis, doughnuts and more through the delights brought to you by dozens of Chicago’s best food trucks.  Guests will also enjoy admission to the zoo, DJs and drinks available for purchase.

Randolph Street Market Festival

When:  The last weekend of each month starting Saturday, May 26th – Sunday, December 16th

Where:  Plumbers Hall

More than 200 vendors will set up their antique housewares, furniture, one-of-a-kind gifts, clothing and more at this Chicago favorite indoor-outdoor festival.  Shop for vintage clothes, jewelry, vinyl, then grab something delicious from the fancy food market and global goods bazaar. You can even bring your own items for appraisal.  And, during the summer months, you can enjoy an expanded outdoor space with even more vintage shops and a beer garden.

Good Libations Beer Fest

When:  Friday, May 25th

Where:  Theater on the Lake, Lincoln Park

This new festival marks the end of Illinois Craft Beer Week, bringing a tropical celebration to the Theater on the Lake.  More than 60 local and out-of-state breweries will be in attendance, sharing island-inspired beer for event goers to sample.  There will also be some good eats on deck from Chicago chef Cleetus Friedman.
Mole de Mayo

When:  Friday, May 25th – Sunday, May 27th

Where:  18th and Blue Island Ave., Lower West Side

Don’t miss out on this true neighborhood tradition, as Pilsen’s annual Mole de Mayo street festival returns to Near South Side to honor the classic traditional Mexican sauce.  The festival features a cook-off, lucha libre wrestling performances and live music. Local art vendors will also show off their wares in the open-air market.

Be sure to mark these festivals down in your calendar, and celebrate the season!  We look forward to sharing in the fun with you!


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