Best Entertainment in Chicago for Kids & Families

Looking for the best entertainment in Chicago for kids? As big-city energy with Midwest friendliness, Chicago offers shows, arcades, and family fun centers 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.

Entertainment venues vary wildly in kid-friendliness. We flag which shows are too long for little ones, which arcades have toddler sections, and whether that 'family' comedy show is actually appropriate for families. 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 entertainment 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.