Things to Do in Chicago in May

As the temperatures climb, restaurants open their decks, sidewalk patios and beer gardens, boats fill the marinas, and the sound of the seventh-inning stretch drifts out of Wrigley Field. Everything good about summer in Chicago starts in May. Some days are still cold, wet and windy, but even a gray afternoon can't keep Chicagoans indoors once they've made it through another winter.

Here's what's on in May, when it usually happens, and what to do when the weather doesn't cooperate. Exact dates move from year to year, so check the city's festival and event dates page or each event's own site before you plan around anything. For weather, crowds and packing, see our planning page, Chicago in May.

Buckingham Fountain switches on

Buckingham Fountain in Grant Park runs from early May through mid-October, depending on the weather. The park district turns it on at a free "Switch on Summer" party. Once it's on, the fountain is open 8am to 11pm, and the big 20-minute water displays start at 9am and go every hour, with the center jet shooting 150 feet up. Go after dark, when the hourly shows add lights and music. It opened in 1927 and it's still the best free show in the Loop.

Farmers markets and outdoor workouts

The city's own farmers markets open in May, including the Thursday market in Daley Plaza, right in the Loop, and the Saturday market on Division Street. The Maxwell Street Market runs one Sunday a month from May through October at 1330 S. Halsted. Green City Market sets up at 1817 N. Clark in Lincoln Park on Wednesdays and Saturdays from 7am to 1pm, with a second Saturday market in the West Loop. More in our guides to farmers markets in Chicago and Green City Market.

Starting in mid-May, the free Millennium Park Summer Workouts take over the Great Lawn on Saturdays. Bring a mat and join in, then walk over to the Bean.

Gardens in bloom

Lurie Garden, in the southeast corner of Millennium Park, has more than 100,000 bulbs planted over the years. Daffodils come first, then the tulips, including big drifts of dark purple 'Queen of Night'. The garden posts a weekly bloom list from March on, so you can see what's flowering before you go. It's free and open 6am to 11pm.

If it's raining, the Garfield Park Conservatory on the West Side runs its Spring Flower Show from February into May, included with general admission. It makes a good Mother's Day outing, as long as that year's show hasn't closed yet. Mother's Day is the second Sunday of May. If you're doing brunch instead, book early. Our list of the best brunch spots is a place to start.

Illinois Craft Beer Week

What used to be Chicago Craft Beer Week became Illinois Craft Beer Week in 2018, to include brewers from the whole state. It still happens in May, with taproom events all over the city. The kickoff is Beer Under Glass, a ticketed tasting with more than 80 Illinois breweries on the Harris Theater rooftop terrace in Millennium Park. Participating breweries sell a commemorative pint glass during the week. Plan your own crawl with our guide to breweries and brewpubs in Chicago.

Cinco de Mayo on 26th Street

Little Village, which Block Club Chicago calls the Mexican capital of the Midwest, has long marked the day with a Cinco de Mayo parade down 26th Street, and local shop owners count on it for sales. Organizers canceled it in 2025 and again in 2026 over fears of federal immigration enforcement, and business owners told the Sun-Times the street was quiet without it. Check whether it's back before you plan around it. The bakeries, taquerias and shops along 26th Street are open either way, and they could use the business.

Baseball and the lakefront

Baseball season is in full swing by May, and a day game at Wrigley Field is about as Chicago as it gets. See Chicago Cubs games for tickets and how to get there, and where to eat and drink near Wrigley.

May is also a good month for the Chicago Architecture Center river cruise, a 90-minute tour led by volunteer docents aboard a First Lady boat. The cruises run from March to November, and May gets you on board before the summer crowds. Boats leave from the southeast corner of the Michigan Avenue Bridge at Wacker Drive. Bring a jacket for the open upper deck. For other ideas, see ways to get out on the water. One thing that doesn't belong on a spring list is Open House Chicago, the architecture center's free weekend inside buildings that are usually closed to the public. That's in October.

Memorial Day weekend

The last weekend in May is the unofficial start of summer, and a lot happens at once.

• The Belmont-Sheffield Music Fest, running for more than 40 years, fills Sheffield Avenue in Lakeview from Friday evening through Sunday. Organizers ask for an optional $10 donation at the gate. Take the Red, Brown or Purple Line to Belmont and you're there.
• The city holds its Memorial Day wreath-laying and parade downtown that weekend. Check DCASE for the date.
• The beaches open. Chicago Park District beaches have lifeguards from the Friday before Memorial Day through Labor Day, 11am to 7pm, and swimming is only allowed then, the park district says. The lake will be cold. See beaches in Chicago.
• Navy Pier starts its free summer fireworks, which run on Wednesday and Saturday nights through Labor Day weekend.

Our Memorial Day in Chicago page has more.

Maifest in Lincoln Square

The German community in Lincoln Square welcomes spring with Maifest, a weekend of food, beer, live music and dancing in late May. In 2026 it moved back to its original home at Lincoln and Western Avenues, by the Western Brown Line stop. It's the first of several street fests on our neighborhood festivals list, and there are plenty more once June hits.

When it rains

May is the wettest month of the year in Chicago, so have a backup. The Art Institute, the Field Museum and the Shedd Aquarium can each fill a day, and the Griffin Museum of Science and Industry in Hyde Park can fill two. Illinois residents get free days at most of the big museums, which we track on our free museum days page. If you'll see several, compare prices on a discount city pass. After dark, catch a show from our theatre guide. There's a longer list of things to do on rainy days, and museums in Chicago covers the rest.

More seasonal ideas are in things to do in Chicago in spring, Chicago in spring and our year-round holidays and events calendar.

Photo by gingerbydesign