Continuing our “summer vacation” in the movies that we’ll do every Thursday in July, this week’s list is the best Chicago movies. That doesn’t mean the best overall movies that happen to be set in Chicago, but the best portrayals of the city in film.
10. Harry and Tonto (1974)
Two unlikely travel partners join together out of desperation and eventually find great joy from each other’s company and friendship. Their travels take them to many parts of the country, but starting in Chicago we see many sites of the great city as they begin their journey together.
9. Chi-Raq (2014)
Dealing with the realities of gang violence in Chicago using the strange but brilliant background of the Greek comedy play Lysistrata, Spike Lee gives a darkly realistic yet shockingly entertaining view in a part of Chicago that is full of hurt and need but ultimately hope.
8. Some Like It Hot (1959)
Though most of the movie is set in Florida, Billy Wilder’s comedy classic begins with the St. Valentine’s Day Massacre, taking us into the world of 1920s Chicago organized crime and prohibition.
7. Airplane (1980)
Whatever isn’t set in the plane is in the O’Hare airport. Unfortunately, that’s the only part of Chicago many people know but it certainly is an important part of the city. And the insane brilliance of the Zucker Bros. anarchic comedy makes the most of the chaotic nature of the busy airport for some of its most hilarious moments.
6. Only the Lonely (1991)
Like Moonstruck‘s view of Little Italy in New York, Chris Columbus’s remake of the 1955 Academy Award winner for Best Picture, Marty, feels almost like it’s set in a small town because the little Irish community we’re taken to in Chicago is so close-knit, closely linked to the culture of the old country. One of the most underrated and too-little-seen romantic comedies gives a very different view of Chicago than we’re used to seeing.
5. Home Alone (1990)
Kevin’s Christmas Eve escape from the armed robbers attacking his house takes us to one of the oldest, most beautiful church buildings in the country and many of the best decorated spots in Chicago at Christmas.
4. I Am a Fugitive from a Chain Gang (1931)
Another interesting look at Chicago crime, this great classic is set mostly in a chain gang where we don’t see much of Chicago, but we hear the characters talk a lot about the city they either love or hate, what they miss about it, and we get a tour of the city through their conversations.
3. Chicago (2002)
Much more than just the title makes the hilarious musical that satirizes the American criminal justice system worthy of this list. Like Some Like It Hot, it shows the thriving of Chicago’s underworld during the time of prohibition.
2. The Blues Brothers (1980)
We get a thorough, though very fast tour of the whole city during what is probably the longest chase scene in movie history. Running from the police, Jake and Elwood drive past and sometimes even through some of Chicago’s most memorable places of interest.
1. The Sting (1973)
And at the top is yet another movie about Chicago crime. Set in the 1930s, there are enough different chase scenes to probably add up to the same amount of time as the long one in The Blues Brothers. But in The Sting, almost all the chases are on foot. Each chase scene is shot in a way that doesn’t just show the shot but gives a unique view of a part of the city.