Never Been Kissed with Drew Barrymore. Caught it on cable over the weekend and it seems the El just jumped out at me.

Ocean's Eleven. All about Vegas, but there is a scene in Chicago with Matt Damon picking pockets on the el.

My Best Friends Wedding for a movie, for actors...Bonnie Hunt and Gary Sinise are both Chicago natives. The movie Return to me was filmed in Chicago and Bonnie Hunt was in that.