Kiddieland started out as a small venture of Arthur Fritz in 1929 when he purchased six ponies and offered rides as an escape for parents reeling from the Great Depression. Miniature gasoline-powered cars were added a few years later after Fritz learned that they were being given away to children by a Chicago newspaper as a subscription promotion.
In 1940, the "German Carousel", two Miniature Steam Locomotives, the "Little Auto Ride", the "Roto Whip" and the "Ferris Wheel" were added. The "Roto Whip" and "Ferris Wheel" would last until the park's closing. The park saw its first major expansion in the 1950s with the addition of the Little Dipper and the Carousel, both of which lasted until the park's closing. Bumper cars were added in the 1960s as they replaced the original pony ride.
The park transferred ownership in 1977, as Arthur Fritz's grandchildren took over the park and its operation. The park continued its expansion and installed several major attractions, including a Log flume, a swinging pirate ship, a 40-foot (12 m) long water coaster, and numerous other attractions.
A dispute developed between Shirley and Glenn Rynes, who owned the land that Kiddieland occupied, and Ronald Rynes, Jr. and Cathy and Tom Norini, who owned the amusement park itself. The landowners sued the park owners in 2004, claiming that the park had an improper insurance policy and that fireworks were prohibited in the lease. The case was thrown out in a Cook County court and later in an appeals court. The landowners declined to extend the lease on the land in early 2009. In late June 2010, it was announced that Kiddieland would be demolished, nine months after the park closed to the public. A Costco store now occupies the land.