Is there anything more classic than the movie-and-dinner combo for date night? Sure, you can go to the movies any season, but summer offers up more opportunities to catch a flick with the city’s many outdoor movie offerings. Lakeview’s Music Box Theatre is playing classic ’90s films like Office Space and Hackers in their outdoor garden space through the end of June, and family-friendly movies will be screened at attractions like Navy Pier, Millenium Park and other Chicago parks all summer long.