It's not often that movies remain popular for as long as John Hughes's 1980's teen classics have-- and it's even more rare to find teen movies that were (and still are) as well received as Hughes's. Part of what makes his movies so awesome is how authentic they are-- which probably has something to do with the fact that he wrote his movies to take place in the suburbs where he grew up, just outside Chicago; he even filmed a majority of them in and around the Windy City, too. So hop in your 1961 Ferrari 250 GT California Spyder (if you can pick one up, I highly recommend it. It is so choice) and head for Illinois to check out some of the many filming locations with this John Hughes guide to Chicago!
Ferris Bueller's Day Off: John Hughes described this movie as his "love letter to Chicago", and it definitely shows. The city's landmarks are highlighted as Ferris and friends ditch school one last time to have the ultimate day off that only Chicago can provide. According to the Internet, the specific day was likely June 5th 1985 based on the baseball game Ferris, Cameron and Sloan attended at Wrigley Field, although the Von Steuben Day Parade (where Ferris jumped on the float and did a rousing lip synch to "Twist and Shout") always takes place in September.
And don't forget, you have to start your trip at Glenbrook High School.
And, you still need to make time to visit the Art Institute Of Chicago, the Chicago Board Of Trade, and The Willis Tower.
The restaurant where Ferris claims to be Abe Froman (the sausage king of Chicago) is a private residence now, so you'll have to find somewhere else to eat (may we suggest The Radler for some tube steaks?)
When your bud spazzes out, take him to Glencoe Beach to unwind before heading back to Cameron's house.
Unfortunately, Ferris Bueller's House is actually in Los Angeles, so if you want to have a final showdown with Ed Rooney, you'll have to get out to California...
Otherwise, visiting Save Ferris Watertower (which, sadly, was repainted) makes for a good ending to your day off.
16 Candles: Who doesn't relate to Molly Ringwald's sassy Sam Baker in this 80's teen classic? First and foremost, there's the high school: the building where the exterior scenes were shot is no longer, but the gym and cafeteria from Niles North High School were used in the film.
Or, stop by Jake Ryan's House-- hopefully there won't be any carnage from a huge rager the night before.
There's also Glencoe Union Church, where Sam's sister's ill-fated wedding took place (word to the wise, go easy on the muscle relaxers).
And, of course, there's always Sam Baker's House: if you look really closely, you just might be able to see Sam and Jake Ryan (swoon to the max) sitting in the bay window by the candlelight of a birthday cake.
The Breakfast Club: John Hughes intended this to be his first film, so he wrote it to take place in one location and feature relatively unknown actors to keep costs down and convince investors to fund the movie-- little did he know that what started as a small movie would become a classic. It was all filmed at Maine North High School, which closed in 1981 and is now a police communications center/Illinois lottery payment office/government building. Fun fact: since the school's actual library was too small, they built a larger library set in the gymnasium.
Oh, and that iconic last scene, where Bender walks across the football field? That was shot at Maine West High School.
Home Alone: KEVIIIIIIIIIN! Roll up to the Home Alone House, where the wily 8-year-old Kevin McCallister spent a few days all on his own in this Christmas classic-- it's actually a really swanky mansion (no wonder the neighborhood was being targeted by burglars in the film).
There's also the pharmacy where Kevin went to buy a toothbrush (preferably approved by the American Dental Association), which is now a Panera, and the church, Trinity United Methodist Church, where Kevin finally talks to the South Bend Shovel Slayer. When you're around the area, just be sure to keep an eye peeled for the Wet Bandits-- those guys can be brutal, and take a beating to boot.
Weird Science: Northbrook Court Shopping Center is a great place to scope out babes, or just have a slushie poured on you by Robery Downey, Jr.
The only houses from the movie that are still standing are Gary's House and Deb's House, though, so don't expect to find a wild party (complete with missiles) at Wyatt's. And, to top it off, the high school was the one that was used in 16 Candles...furthering the theory that all of John Hughes's movies take place in the same universe (which I, for one, want to believe so bad).