First, be sure that the films you're showing are ones that are of interest to the general audience. Films, which don't appeal to a considerable number of people, have no value when shown. There are several film companies available from which to rent. Since they handle many of the same films, be sure to shop around and get the best deal you can. Also, if you're planning a series of movies, it may be beneficial to get them from the same distributor since they may give you a discount rate on a package deal.
Many public libraries have films available to members for free or for a minimal charge.
Though their catalogues of films may not be extensive, many organizations have found that they can provide a few evenings of entertainment for very little money. Catalogues tend to extend from 1940 educational films to relatively current feature films. Comedy shorts are normally available as well. You could also check the Chicago Public Library system. Ordering the Film You may call the distributor or write to them.