Best of May: 50 Things To Do in Chicago with Kids for Mother's Day, Memorial Day Weekend, and More

Celebrate Chicago River Day this month! Photo courtesy of the Friends of the Chicago River, Facebook
Celebrate Chicago River Day this month! Photo courtesy of the Friends of the Chicago River, Facebook

Get ready for a lot of pictures of Justin Timberlake on your Facebook feed because It's Gonna Be May! Parades are back and there are two big ones downtown this month: The Polish Constitution Day Parade and the Memorial Day Parade. Has being outside again got you thinking about nature?  Check out environmentally themed fun at Chicago River Day, World Migratory Bird Day or Cosley Zoo's Party for the Planet. Fairy tales are also a big theme this month, with a new presentation of Into the Woods in Des Plaines, Once Upon a Symphony performing Jack and the Beanstalk,  Lookingglass Alice on the Mag Mile, and Alice in Wonderland from the Salt Creek Ballet. If all of that is enough to make you want to go fly a kite, you can do so in Wheaton or Homer Glen.

There's still time to book a reservation at one of our top 25 destinations for Mother's Day brunch, or to plan another activity for Mother's Day. Check out one of our favorite tot lots and toddler playgrounds to get your littlest kids out and moving. Or get away from it all with a hike in or around the Windy City.

Here are some of our favorite things to do in May with kids in Chicago!

While we are trying to promote safer activities that occur outdoors or with social distancing guidelines in place, please keep your family and others safe by always wearing a mask and maintaining an appropriate distance. If you arrive at an event that appears too crowded, try using the “nearby” search feature on our event calendar to find something else to do

Places featured in this article:


Tinley Junction Mini Golf and Batting Cages

Lake Ellyn Park & Boathouse

Zoom - Online

Zoom - Online

Zoom - Online

Zoom - Online

Hard Rock Cafe Chicago

McCormick & Schmick's Chicago

McCormick & Schmick's Oak Brook

Eckhart (Bernard) Park

Herrick Lake Forest Preserve

Little Red Schoolhouse Nature Center

Midewin National Tallgrass Prairie

North Branch Trail (south trailhead)

North Park Village Nature Center
Bitter Jest Musical Festival
Port Clinton Square - 6:00 PM Pick
Art on the Mart
Merchandise Mart - 8:30 PM Pick
Movies in Cantigny Park
Cantigny Park - various times Pick
Westmont Spring Fling Red, White and BBQ
Ty Warner Park - various times Pick
Mole de Mayo
18th and Ashland - various times Pick
Neighborhood Guides
Activity Guides