Chicago has long been a haven for film-makers, with its extensive mob history and architecture and the various neighborhoods, sports-team obsessed fans, beautiful lakefront views, the emblematic EL train and iconic eateries.
Cult rom coms like When Harry Marry Met Sally and Drinking Buddies, coming-of-age movies ranging from Ferris Bueller’s Day Off to Sixteen Candles, mob movies like The Untouchables to adventure blockbusters like The Dark Knight and Divergent were all filmed in this lake front city. Check out some emblematic spots here (most of which are reachable by public transportation)! For the more avid watchers there are guided tours.
Chicago Union Station
Chicago Union Station, other than home to millions of passing travelers, is also home to the momentous shootout in The Untouchables, in addition to Michael Mann’s Public Enemies where the 110 foot atrium and gigantic marble floor time travel to the notorious mob history. Other famous Chicago gangster films have taken place on the same marble floor including Road to Perdition. So catch Oscar-winner Sean Connery in a movie about the infamous Al Capone amidst an already historic Chicago landmark. Also check out its appearance in My Best Friend’s Wedding.
“The L” Train
Emblematic of the Chicago experience, The L not only gets some serious face time in The Dark Knight, but it also (quite appropriately) plays a huge role in John Hughes film Planes, Trains, and Automobiles. Steve Martin and John Candy say their goodbyes before Martin has an epiphany that leads to a key scene in the movie – which we won’t spoil but look here for details. It’s also the site of A true to name Risky Business sex scene on the train. The train is also featured in the brimming romance of the protagonists, one of which is played by Miley Cyrus in the Chicagoan take of the French Film LOL.
As you can imagine, prime scenes of many a baseball movie have taken place at Wrigley Field including A League of Their Own, Rookie of the Year, About Last Night, 8 Men Out, and Hardball just to name a few. A League of Their Own makes the on-screen jump back to 1943 before women, as the title suggests, had a league of their own, and illustrates the story of Geena Davis’ effort to make it happen. It also is also prominently featured in the hit – pun intended – film Rookie of the Year. The story details the somewhat goofy story of a unexpected accident turning a less than talented 12-year-old little league player into an all-star pitcher for the Cubs with an almost mechanically precise arm.
Music Box Theatre
John Cusack, already a component of Chicago history, filmed part of High Fidelity at the Music Box Theatre about a music snob living in Chicago. Rob, the protagonist snob, visits the Music Box and Biograph’s theatres as well as a variety of other Chicago spots.
O’Hare International Airport
The glam airport that a young Macaulay Culkin finds himself lost in is the setting of the second in the series of the family classics Home Alone 2. After the McCallisters depart from their Winnetka home, they race through O’Hare to make it to Terminal 3 but lose their troublemaking son in the process.
Volcanic Iceland Epic Trip
meet our Local Insider
HOW LONG HAVE YOU BEEN A GUIDE?
WHAT DO YOU LOVE ABOUT YOUR JOB?
It's the personal contact, the personal experiences. I love meeting people from all over the world... I really like getting to know everyone and feeling like I'm traveling with a group of friends.
WHAT DESTINATION IS ON YOUR TRAVEL BUCKET-LIST?
I have so many places on my list, but I would really lobe to go to Africa. I consider myself an “adventure girl” and Africa feels like the ULTIMATE adventure!
Every CULTURE TRIP Small-group adventure is led by a Local Insider just like Hanna.
KEEN TO EXPLORE THE WORLD?
Connect with like-minded people on our premium trips curated by local insiders and with care for the world
Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.
Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.
Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.
Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.
We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.