Things to Do in Chicago in May

After the rainy spring season, most Chicago locals and visitors want to head outdoors and enjoy the thrilling activities the city has to offer. You’re in luck! We’ve got a list of things to do in Chicago in May that will leave you craving more fun in the sun throughout the summer season.

Chicago Beer Classic

If you’re a fan of authentic brews and summer fun in Chicago, May is the best time to make your way downtown to Soldier Field for this Chicago festival. Several local and national brewers kick off the summer at this popular May Chicago event that features not only brews, but also food, music and fun. Join in the tailgate activities before the event and then head onto Soldier Field to sample some of the best beers in the city.

Walking Tours

When the weather is not yet too warm and muggy, yet a cool breeze is abundant, put on your walking shoes and sightsee the downtown area on foot with a guided Chicago walking tour. See Chicago architecture, listen to city-related ghost stories and span the neighborhoods and Chicago attractions. Hosted by Greeter Tours these walking tours offer you and the family the perfect opportunity to have some fun in the city in May while also getting in some exercise.


What better way to experience Chicago than by attending one of the city’s most popular festivals? MaiFest, hosted in Lincoln Park, is one of the most popular kick-offs to summer with food, live entertainment and games for all ages. This popular German festival is hosted the last weekend of May each year. Join in the Gemütlichkeit this year to treat the family!

Night Nation Run

If you love music and running, combine the two by participating in Chicago’s Night Nation Run event in May. This Chicago festival includes a 5K run, a light show, an illuminated race course, lasers, celebrity DJ performers and a main stage after party. The best part is that you get to run along the Chicago riverfront with spectacular views of the city’s skyline.

May is the perfect time to get out and about with the family or that special someone. And, Chicago attractions give you plenty of opportunities to enjoy the windy city in style. From walking tours that get your heart rate moving to homemade brews at May Chicago festivals, you can find just the right activity that suits your needs. Check back often for even more suggestions for enhancing your time in downtown Chicago.

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