One of 22 independent park boards consolidated into the Chicago Park District in 1934, the Hollywood Park District formed in 1926 to provide recreational space for the northeastern portion of Chicago's North Park community. The fledgling park district began purchasing property two years later in 1928, acquiring 2.75 acres through 25 separate purchases by 1931.  Land acquisition for the park was not completed until 1949.  The site was known as Hollywood Park. Both the park and the district take their names from Hollywood Avenue, which runs through the North Park neighborhood. John Lewis Cochran, the subdivider of nearby Edgewater and a one-time resident of California, named the street for the West Coast Hollywood. Improvements began in 1931, as soon as land acquisition was complete. Within a year or two, Hollywood Park had an attractive rocky-edged goldfish pond. Concealed pipes brought water to the high points of the stone work, sending streams cascading into the pool below. Although the pool had prairie-style influences, it incorporated a variety of flowers and trees from China and Japan. Hollywood Park's design also featured a flagstone walk, a playground, a wading pool, and a baby pool with a pergola shelter. A neighboring lot was flooded for ice skating in winter. Due to the financial crisis caused by the Great Depression, this was the sole project of the Hollywood Park District. The Chicago Park District took control of the park in 1934, and rehabilitated the pond the following year. The Park District acquired additional property after World War II, more than doubling the park's size. In constructing a fieldhouse and various outdoor recreational facilities in the enlarged park, the pond and much of the original stonework was removed. Twenty years later, the Park District constructed a new spray pool and a fieldhouse addition. Improvements made during the 1990s included installation of a soft surface playground and ornamental iron fencing.

Located at the corner of Jersey and Peterson Avenues, Hollywood Park totals 7.14 acres, with a small fieldhouse, two softball fields, four basketball standards, tennis court, volleyball court, Chicago Plays! playground, and a spray pool.

For its youngest park-goers, Hollywood Park offers preschool, play group, recreational tumbling, and, in the summer, play camp. Youth participate in programs such as arts and crafts, fun and games, after school drop-in, or table fun and games. Teenagers play basketball or become a member of teen club. Adults can help beautify the North Park neighborhood by lending a hand with the park’s community garden. Table tennis is available to be played by all.