Best Seasonal Events in Chicago for Kids & Families

Looking for the best seasonal events in Chicago for kids? As big-city energy with Midwest friendliness, Chicago offers holiday celebrations, festivals, and limited-time experiences that families won't find anywhere else. Whether you're visiting for the first time or looking for something new, we've rated every option for age-appropriateness, stroller access, and value so you can skip the guesswork.

Seasonal events are some of the most memorable family experiences — but they sell out fast and often have age restrictions that aren't obvious on the website. We update dates, pricing, and age recommendations as events are announced. In Chicago, expect legendary winters — summer is prime family season. Fall is stunning but brief.. Pro tip: CityPASS saves serious money on the top attractions. Many museums have free days — check schedules.

Below you'll find our curated list of seasonal events in Chicago, IL — each with detailed age ratings (infants through teens), cost estimates for a family of four, and the practical parent details that matter: parking, stroller access, nursing rooms, and honest reviews of what makes each spot worth your time.