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Lately, away from the website, I've been thinking about and getting more and more interested in the big city I now live in, namely Chicago, Illinois.  You can probably thank the Stanley Cup winning Chicago Blackhawks for doing that lately.  For those who don't know me, I grew up on a dead-end country road about an hour south of the city in a little town called Peotone.  The "Windy City" and "Second City" of Chicago has always been a close and accessible mecca of cultural enrichment and urban excitement just a stone's throw of traffic away.

With my career evolving in the past two years from elementary school teacher to an instructional coach for a charter school company, I get to call the city itself home.  At the office of my work, I count as the the local-est of the locals in a office of mostly former foreigners.  I somehow have become the unofficial "tour guide" and host for visiting teachers and company members.  I've had a blast showing off the history, architecture, sights, and sounds of Chicago to new visitors of this gorgeous city.  There's just to much to show, from the two tallest buildings in the country to oldest bricks and pieces.

As a movie nerd at heart, the visuals of the city and its skyline that have shown up in popular movies have become my go-to landmarks and conversation starters.  I point to a spot, mention the movie, and it all clicks.  Since it's been quite a while since I've written a good editorial "10 Best" list, I've decided to make Chicago the subject.  Here, with a couple of shameless ties, are my picks for the ten best movies filmed and set in Chicago.  The three rules for making this list were:

1. The movie had to be predominantly filmed in and around Chicago, NOT somewhere else standing in for Chicago.
2. The movie had to be set in Chicago, NOT using the city as a backdrop for something or somewhere else.
3. The movie had to show the city off in a beautiful or unique way.

It was a hard list to narrow, but here are my picks.  Enjoy and chime in with your own picks and votes in the comments section!  

(Listed movie images: www.imdb.com)

1. Ferris Bueller's Day Off-- The top spot is an absolute no-brainer.  This 80's classic might as well be a unofficial tour of the Chicagoland area.  No other movie is as cool or covers as much of the city's glory.  We all wanted to ditch school, join Matthew Broderick, Alan Ruck, and Mia Sara, as they took in the Art Institute, a Cubs game, the Sears/Willis Tower, the Chicago Mercantile Exchange, eat at a fine restaurant, and crash a parade while prancing about in a vintage Ferrari (and future "sarcastic guy-cry" subject).  While I would love to mark this movie down for Alan Ruck wearing a Red Wings sweater all movie, there's too many great things that outnumber that.  The late great John Hughes, who moved to the Chicago area as a teen from Michigan, wrote, filmed, and set many of his cult (and not-so-cult) classics (both as a writer and a director) in and around Chicago.  I could fill this entire list with just his movies like The Breakfast Club, Sixteen Candles, Weird Science, Uncle Buck, National Lampoon's Christmas Vacation, Home Alone, Dennis the Menace, and Baby's Day Out.  To be fair, I'm only going to give Hughes credit for one and Ferris Bueller's Day Off is his best movie at showcasing the city of Chicago.  It earns the number one ranking.   (trailer)

BEST CHICAGO SCENE:  That awesome parade scene is the best of so many to choose from.

2. The Fugitive-- A distant, but worthy second place is Harrison Ford's wrongfully-accused 1993 thriller.  While Ferris played casual tour guide, Ford's Richard Kimble made his stomping grounds the playing field for clearing his name for his wife's murder and dodging the hot pursuit of Tommy Lee Jones' U.S. Marshal and posse.  With all the necessary Chicago stereotypes (the accents, the weather, the sports, the cops, etc.) and some incredibly quotable lines (especially when performed by local sports radio personalities like Mark Grote), the movie  trampled around hotels, rooftops, and parades with its cat-and-mouse game, putting the city in the center of the action.  It also earns points for casting actual Chicago media members in similar roles.  (trailer)

BEST CHICAGO SCENE:  Watching the chase for Richard Kimble cross paths with the downtown St. Patrick's Day parade, dyed green river and all.

3. Backdraft-- I'm going to surprise some people by putting this movie so high, but I think it's an incredible movie for giving the city of Chicago some real heroic character.  Chicago has always been proud of its blue-collar background.  It's a city at the crossroads of multiple immigrant heritages that have taken on Midwestern values.  You can't get more blue-collar and heroic than an intermingled family tree of Chicago firefighters played by Kurt Russell, William Baldwin, and Scott Glenn (all of which did many of their own stunts).  I've previously ranked Backdraft as my #1 firefighter movie and it earns its stripes as a pure Chicago movie as well.  Filmed all over the city's neighborhoods for fire locations, these are the guys on this list that you want to go have a beer with.  You won't have Rescue Me or Chicago Code as TV hits without Ron Howard's Backdraft paving the way on the silver screen.  (trailer)

BEST CHICAGO SCENE:  Not to keep the parade thing going, but that massive firefighter funeral march through downtown is impressive.

4. The Blues Brothers-- I'm going to get some crap for putting this Chicago favorite so low, but I stand by this ranking, especially after reviewing the merits of the Top 3.  The Blues Brothers put Chicago back on the  Hollywood map in 1980 after most movies skewed to L.A. or New York.  There's a good chance the amount of drugs used by the cast members also put the Chicago drug scene back on the map.  Kidding aside, the movie does a bang-up job, literally and figuratively, in bouncing around the city and suburbs.  That car chase through the former Dixie Square Mall in Harvey comes to mind the most.  Where I put the movie down a few rungs, according to my aforementioned criteria, is that it spends an awful lot of time indoors at singing gigs.  Ferris's parade karaoke trumps "Jailhouse Rock."  Sorry, but it does.  (trailer)

BEST CHICAGO SCENE:  The mall chase, hands down.

5. The Untouchables-- Ask just about any educated American outside of Chicago who Al Capone was and they will bring up the city of Chicago.  To many, he's likely the most famous former resident of the Windy City.  By far, the best Al Capone movie Hollywood has produced is Brian DePalma's crime opus The Untouchables from 1987.  Kevin Costner was nearing the height of his stardom as Capone crimefighter Elliot Ness and Sean Connery netted his only Academy Award as his right-hand man versus Robert De Niro's Capone.  Of all of the movies on this list, I think The Untouchables does the best job of showing off the city's historic and groundbreaking early 20th century architecture, inside and outside, much of which still stands today.   Michael Mann's Public Enemies can't come close to The Untouchables  in that regard, neither can Sam Mendes's Road to Perdition.   (trailer)

BEST CHICAGO SCENE:  Astute movie fan eyes will notice that the climatic battle in this summer's Man of Steel ends in the same train station (Union Station) where this film's slow-mo baby rescue shootout occurred.  A close second goes to "batter up!"

6.  (TIE) High Fidelity and Love Jones-- I'm going with a pair of very different romances next that show smaller sides of Chicago.  Evanston native John Cusack is one of the "favored sons" of Chicagoland-bred actors.  When British director Stephen Frears adapted Nick Horby's novel High Fidelity and moved the setting from London to Chicago, they made a cult hit with Cusack in the lead of Jack Black's coming-out party.  Filmed at a fictional record store in the trendy Wicker Park neighborhood, High Fidelity showed an approachable and accessible Chicago and a rich underground music scene away from the glamorous downtown traps and sunny suburbs.  

The same goes for Love Jones, a little 1997 movie that many of you probably haven't seen or heard of.  Menace II Society's Larenz Tate and The Best Man's Nia Long play a hot-and-heavy, on-again/off-again pair of lovers with a penchant for poetry and old music.  First-time filmmaker Theodore Witcher's goal with this gem of an independent film was to show a modern slice of African-American adults that didn't revolve around drugs or crime.  In a city where 1/3 of the population is in the African-American demographic, he succeeded with a mature romantic drama that also highlighted the little neighborhoods between the skyscrapers.  (trailer and trailer)  

BEST CHICAGO SCENE #1:  One of John's character's many Top 5 lists in High Fidelity, this one about what she misses about his departed girlfriend overlooking downtown and the river.

BEST CHICAGO SCENE #2:  It's indoors, but "A Blues for Nina" by Larenz Tate, working the spoken word in Love Jones is the best scene in the whole darn movie.  

7.  My Best Friend's Wedding-- Now, I'll go from two quirky neighborhood romances to a string of four romantic comedies in a row.  Narrowly beating the tie at #8, is America's Sweetheart Julia Roberts and My Best Friend's Wedding.  She invaded Chicago as a food critic in the summer of 1997 trying to bust up Dermot Mulroney and Cameron Diaz's wedding.  The movie makes great use of many city locations, from U.S. Cellular Field (then Comiskey Park), Union Station, the water taxis of the Chicago River, O'Hare Airport, and much more.  Of the four romantic comedies on this list, My Best Friend's Wedding does the best job at showcasing the city while still being the superior film of the group.  I wish I could include the Chicago-set My Big Fat Greek Wedding, but it was Toronto stood in for Chicago.  More on that later.  (trailer)

BEST CHICAGO SCENE:  Julia and Dermot's characters share a heart-to-heart and missed opportunity on a one-on-one boat ride down the Chicago River.  

8.  (TIE) Return to Me and While You Were Sleeping-- Of this next tie, Sandra Bullock's While You Were Sleeping is the best-known one of the two.  The 1995 film came out the same year as Speed, launching Bullock as America's other sweetheart.  Playing a CTA token collector (which the city doesn't have anymore) attracted to Peter Gallagher (and later Bill Pullman), the "L" elevated train system gets a nice starring role, particularly the State/Lake and Randolph/Wabash stations.  It's one of my wife's favorites.  I counter that with a movie I think is better than While You Were Sleeping.  

2000's Return to Me, starring David Duchovny and Minnie Driver, surrounds a Chicago architect (Duchovny) who tragically loses his Lincoln Park Zoo anthropologist wife in an auto accident and becomes a sullen mess.  Soon, he becomes drawn to a waitress and heart transplant survivor (Driver) who works at a Irish-Italian restaurant.  It's the ensemble around the couple that really makes this movie tick.  Bonnie Hunt, Jim Belushi, David Alan Grier, Robert Loggia, and Carroll O'Conner (in his final film appearance) are an absolute hoot.  If you've never seen it, go seek it out.  (trailer and trailer)

BEST CHICAGO SCENE #1:  Return to Me's fun "Swiss Water" scene is pretty good at showing the ensemble charm of the movie and gives us the necessary "meet cute" for a romantic comedy.

BEST CHICAGO SCENE #2:  Come on, ladies in sweatpants watching While You Were Sleeping  again, that happy ending seals the deal (loose spoiler).

9.  The Break-Up-- The last Chicago romantic comedy of four to make the list is Vince Vaughn and Jennifer Aniston dueling with each other's needs and wants in The Break-Up, a movie where they became a real-life item for a time.  Since this 2006 movie and others (including the far-lesser, Ron Howard-helmed The Dilemma from 2011), Vince Vaughn has likely usurped the torch from John Cusack (who took it away from Jim Belushi a generation before) as the current "favored son" of Chicago-tied actors.  Vaughn plays a chatty (naturally) tour bus guide who out-kicks his coverage with an Aniston that wants more than a slacker.  My favorite Chicago scene in the movie isn't the Old 97's concert at the vintage Riviera Theater, it's the "Crosstown Classic" Wrigley Field scene that opens the movie.  Before Nick Offerman and Craig Robinson did it better in three New Era commercials, it was a treat to watch the not-so-subtle ball-busting between Jon Favreau's White Sox fan and Vaughn's Cub fan in a Swingers reunion.

BEST CHICAGO SCENE:  The aforementioned Wrigley Field banter  that opens the movie.

10.  Rookie of the Year-- Speaking of Wrigley Field, as a Cub fan, I can't leave Rookie of the Year off of this list.  With filming locations that including Oak Park, Westmont, and U.S. Cellular Field/Comiskey Park standing up for Dodgers Stadium, no Hollywood movie has shown the lovable losers that are the Chicago Cubs better than this.  It earns extra points for ruining Thomas Ian Nichols when we see in in the American Pie series years later and getting Gary Busey to play it straight and not crazy.  Unfortunately, we can't say the same for Daniel Stern and his sunflower seed-chomping ways.  (trailer)

BEST CHICAGO SCENE:  Funky butt-lovin'!  Watch and you'll see why.

11. The Road to Perdition-- I want to stop at ten, but I have to expand this list to eleven for just one more.  The last movie for the list is an excellent bookend to The Untouchables from up higher on the list.  Sam Mendes'Road to Perdition from 2002 is an outstanding crime drama about fathers and sons, bolstered by an against-type performance from Tom Hanks, the always-perfect Paul Newman, and smaller roles from Jude Law, Stanley Tucci, and Daniel Craig.  It was his follow-up to his Oscar-winning American Beauty.  The movie takes a while for it to reach the gilded streets of Chicago (which leads to its lower rank on this list), but Mendes and company did an excellent job scouting out and hunting down the little Main Street business districts, rural roads, and old bank fronts of many Chicagoland towns, particularly south of the city in Will and Kankakee counties, for the robberies at the center of the movie.

BEST CHICAGO SCENE:  I can't find the exact clip, but there's a dynamite establishing shot over a city bridge when Tom and son arrive to town, hinted at in trailer.

(Image: movies.stackexchange.com)

SPECIAL MENTION: They break the rule of not being set in Chicago, but Batman Begins, The Dark Knight and Man of Steel were all predominantly filmed in Chicago, which stood in for the fictional Gotham City and Metropolis locations.  All three comic book flicks utilized the great and proud skyline to be the prototypical American big city.  Take that New York!  I know anytime I drive my car on Lower Wacker Drive, I pretend my car is the Tumbler and that pulsing Hans Zimmer music comes on.  Any Chicagoan who watches those movies sees their digs as the home to a pair of superheroes.

BEST CHICAGO SCENE:  Here's the excellent Tumbler chase from Batman Begins.  

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TORONTO: "THE SECOND-SECOND CITY"--Toronto has long been Hollywood's go-to modern city stand-in for both Chicago and New York with its urban architecture and Western World look.  Simply put, it's cheaper to film in Canada than in the U.S. sometimes.  Prominent movies "set" in Chicago, but predominantly filmed in Toronto include: Adventures in Babysitting, Chicago (yes, the Oscar-winning movie penultimately named Chicago), John Q., The Time Traveler's Wife, My Big Fat Greek Wedding, and The Vow.  They are, sadly, all disqualified from making the master list.  Fellow Canadian cities Montreal and Vancouver stole most of the Chicago looks for Source Code and I, Robot respectively as well.

HONORABLE MENTION

Finishing the TOP 20 (movies not good enough to make the final cut)

12. Medium Cool  (great history of the famous 1968 Democratic National Convention riots in Chicago)

13.  Primal Fear  (great crime film, too much time inside away from the city)

14. The Negotiator  (great cop film, too much time inside away from the city)

15. The Relic  (guilty pleasure creature-feature set and filmed at the Field Museum of Natural History)

16. Roll Bounce  (fun use of the city's old roller rinks)

17.  Barbershop  (mostly soundstage, but a little bit of Chicago exterior for both)

18.  Soul Food  (see Barbershop)

19. Save the Last Dance   (chicks dig it)

20. Candyman  (the best use of Chicago for horror in making Cabrini Green look more scary than it was)

Others (in no particular order):  A Keanu Reeves triple pack (The Watcher, Hardball, The Lake House), About Last Night..., Risky Business, What Women Want, Red Heat, Stir of Echoes, Code of Silence, Henry: Portrait of a Serial Killer, Prelude to a Kiss, Thief, The Breakfast Club, Uncle Buck, Home Alone, A League of Their Own, Derailed, Mad Dog and Glory, The Dilemma, Child's Play, Wildcats, Above the Law, The Hunter, Chain Reaction, Nothing in Common, Bad Boys (1983), the Sears Tower ending of Michael, and the ending city-versus-robot slug fest of Transformers: Dark of the Moon.

(Image: cinematreasures.org)