Chicago in the Movies: The 9 Most Famous Spots

Chicago Skyline
Chicago Skyline | © Allen McGregor/WikiCommons
Ilana Herzig

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 1943

1. Chicago Union Station

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.

500 W Jackson Blvd, Chicago, IL 60605, United States

UChicago Gate © Rdsmith4 / WikiCommons

2. University of Chicago

Park, University

The Rom-Com about whether men and women can really be friends, When Harry Met Sally, aptly begins its journey on this English gothic-style college campus in the neighborhood Hyde Park. A shot of the beautiful Chicago campus opens preceedings where we meet Harry and Sally for the first time, as fresh-faced college grads about to embark on the stereotypical move to The Big Apple to find themselves. The warbled tones of Louis Armstrong’s Our Love Is Here To Stay crescendos as Harry and Sally drive out the UChicago Gate to start their new lives as New Yorkers.

“The L” Train

The Art Institute of Chicago

3. The Art Institute of Chicago

Museum, Art Gallery

The towering glass and stone exterior of the Art Institute of Chicago
© Richard Ellis / Alamy Stock Photo
A key scene in the classic movie Ferris Bueller’s Day Off takes place in the Art Institute featuring Cameron doing a bang up Magic Eye impression as he stares off into space at George Seurat’s “A Sunday on La Grande Jatte.” The most impressive part” They manage to condense over one million square feet of museum into a miraculous two-minute trip.

4. Wrigley Field

Sports Center, Park

The legendary marquee of Wrigley Field. Wrigley Field is a baseball park located on the North Side of Chicago, Illinois. It is the home of the Chicago
© Jose Campos / VWPics / Alamy Stock Photo

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.

5. Wicker Park

Brewery, Music Venue, Park

The more recent film Drinking Buddies staring the one and only Olivia Wilde, features multiple spots in the “hipster” neighborhood of Wicker Park. A good portion of the movie actually takes place in the protagonists’ place of work Revolution Brewing, an actually brewery with two nearby locations in Avondale and in the Logan Square neighborhood. The protagonists also shoot pool at cool music venue: The Empty Bottle.

6. Pump Room

Restaurant, American

This popular food spot gets its 15 minutes of fame in John Hugh’s 80’s film The Body Guard, where Cliff (the new kid on the block) dines nightly at the Ambassador East Hotel’s restaurant. Go for an omelet for brunch or check out the spot for its air time significance.

7. Music Box Theatre

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.

3733 N Southport Ave, Chicago, IL 60613, United States

O’Hare Concourse C | © Andrew E. Larsen / Flickr

8. O’Hare International Airport

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.

10000 W O’Hare Ave, Chicago, IL 60666, United States

landscape with balloons floating in the air


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.

Winter Sale Offers on Our Trips

Incredible Savings

Edit article