Twelve films will be featured throughout the season, starting with the Oscar winning hit Chicago. Dreamgirls and Moulin Rouge are also on the bill.
The films will be shown on a state-of-the-art giant, LED screen.
Moviegoers can sit in seats or have a picnic on the lawn at Pritzker Pavillion.
The program begins Tuesday, June 18, which would have been film critic Roger Ebert's 71st birthday. Ebert often opened Chicago's free movie season at the park.