Best movies like Windy City
Last updated March 2024
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Plot Summary:
The lives of a group of young Chicago men, as seen through the eyes of one of them, a writer.
IMDB Rating: 5.8
IMDB Votes: 311
Genere: Drama, Romance
Country: USA
Duration: 103 min
Plot tags: independent film, nostalgic
Best tv shows and movies like Windy City (1984):
Similar in 78%
Threesome (1984)
Plot Summary:
A New York stockbroker (Stephen Collins) introduces a girlfriend (Deborah Raffin) to his buddy (Joel Higgins) from out of town, then regrets it.
IMDB Rating: 6.9
IMDB Votes: 48
Genere: Drama, Romance
Country: USA
Duration: 100 min
Plot tags: sex comedy
Similar in 77%
The Souler Opposite (1998)
Plot Summary:
Barry (Christopher Meloni) is a bitter, sexist thirtysomething stand-up comic with a penchant for aggravating the wrong people. When his act provokes a knuckle sandwich one night, the sensible, idealistic and much younger Thea (Janel Moloney) picks him up. Although the two have nothing in common, that doesn't stop them from falling in love. Romance is rough, however, when opposites attract in this thoughtful romantic comedy.
IMDB Rating: 5.5
IMDB Votes: 190
Genere: Comedy, Drama, Romance
Country: USA
Duration: 104 min
Plot tags: independent film
Similar in 82%
A Christmas Stray (2021)
Plot Summary:
A man finds himself hopelessly stranded in a small town on Christmas Eve, unable to shake the stray dog who ran him off the road, and irresistibly drawn to the free-spirited, local veterinarian.
IMDB Rating: 6.2
IMDB Votes: 337
Genere: Drama, Romance
Country: Canada, USA
Duration: 84 min
Plot tags: sincere, captivating, disturbing
Similar in 88%
How Not to Disappear Completely (2015)
Plot Summary:
'How Not To Disappear Completely' follows a week in the life of a young photographer Tom as he returns to London after spending two years traveling in India. Tom is at a crossroads in his life. A stranger in the cold hard city, he struggles to reconnect with his friends whilst searching for his half sister. Along the way Tom is forced to face up to his past and soon realises that it may not be his life he's been running away from but himself.
IMDB Rating: 8.3
IMDB Votes: 14
Genere: Drama, Romance
Country: UK
Duration: 74 min
Plot tags: psychological, sincere, touching, melancholic
Similar in 76%
The Photograph (2020)
Plot Summary:
When famed photographer Christina Eames dies unexpectedly, she leaves her estranged daughter, Mae, hurt, angry and full of questions. When Mae finds a photograph tucked away in a safe-deposit box, she soon finds herself delving into her mother's early life -- an investigation that leads to an unexpected romance with a rising journalist.
IMDB Rating: 6.1
IMDB Votes: 6000
Genere: Drama, Romance
Country: USA, China
Duration: 106 min
Plot tags: uplifting, disturbing, sweet, romantic, romantic comedy, visual, romantic drama, touching, sentimental
Similar in 82%
LAID: Life as It's Dealt (2012)
Plot Summary:
A young male escort falls for the "girl next door", only to find himself caught between two colliding worlds.
IMDB Rating: 6.7
IMDB Votes: 30
Genere: Drama, Romance
Country: USA
Duration: 105 min
Plot tags: sexy, touching, light, sincere, romantic, captivating, erotic, independent film
Similar in 88%
Friends of Friends (2002)
Plot Summary:
Dominik Graf relocates the story of the same name by Henry James from the 19th century to the year 2001.
IMDB Rating: 6.9
IMDB Votes: 280
Genere: Drama, Romance
Country: Germany
Duration: 89 min
Plot tags: light, romantic, captivating, entertaining
Similar in 81%
The Accidental Tourist (1988)
Plot Summary:
After the death of his son, Macon Leary, a travel writer, seems to be sleep walking through life. Macon's wife, seems to be having trouble too, and thinks it would be best if the two would just split up. After the break up, Macon meets a strange outgoing woman, who seems to bring him back down to earth. After starting a relationship with the outgoing woman, Macon's wife seems to think that their marriage is still worth a try. Macon is then forced to deal many decisions.
IMDB Rating: 6.7
IMDB Votes: 17000
Genere: Drama, Romance
Country: USA
Duration: 121 min
Plot tags: sentimental, touching, emotional, depressing, humorous, melancholic, sincere, realistic, talky, offbeat
Similar in 85%
Dean (2016)
Plot Summary:
A freelance illustrator in New York suffers a quarter-life crisis and leaves his home for the west coast.
IMDB Rating: 6.3
IMDB Votes: 3000
Genere: Comedy, Drama, Romance
Country: USA
Duration: 94 min
Plot tags: romantic, humorous, disturbing, semi autobiographical, independent film
Similar in 90%
One Week (2000)
Plot Summary:
A soon-to-be groom learns that he may have contracted HIV. Waiting a full seven days for the test results turns out to be the most hectic week of his life.
IMDB Rating: 6.4
IMDB Votes: 272
Genere: Drama, Romance
Country: USA
Duration: 97 min
Plot tags: touching, psychological, sincere, serious, realistic, contemplative
Similar in 82%
Noah's Arc: Jumping the Broom (2008)
Plot Summary:
As Noah and Wade prepare to marry in Martha's Vineyard, the personal problems of their friends - and the unexpected arrival of rapper Baby Gat - threatens to permanently end their relationship.
IMDB Rating: 6.7
IMDB Votes: 888
Genere: Drama, Romance
Country: USA, Canada
Duration: 101 min
Plot tags: touching, humorous, realistic, witty, semi serious, crying, queer cinema
Similar in 75%
XX/XY (2002)
Plot Summary:
When two college students, Sam and Thea, meet Coles at a party, their mutual attraction is immediate, leading to a passionate and awkward night together, and the onset of an intensely charged bond. As they continue to push the sexual boundaries of their friendship, however, they are tested by Sam and Coles' incipient romance and Thea's increasing recklessness, until the relationship dissolves amid a cloud of fear, resentment and mistrust. Eight years later they reunite. An animator for a high-profile ad agency, Coles now lives with Claire, his girlfriend of five years. Thea is happily married to Miles, with whom she owns a flourishing restaurant. And Sam has just returned to Manhattan after working in London where she recently broke off her engagement. Yet upon reconnecting, the three are drawn back into the complicated dynamic that defined their relationship from the start and are forced to confront the true meaning of commitment and love.
IMDB Rating: 5.9
IMDB Votes: 3000
Genere: Drama, Romance
Country: USA
Duration: 91 min
Plot tags: melancholic, intense, psychological, touching, humorous, erotic, art house, independent film, talky, sensual
Similar in 86%
Texasville (1990)
Plot Summary:
Summer, 1984: 30 years after Duane captained the high school football team and Jacy was homecoming queen, this Texas town near Wichita Falls prepares for its centennial. Oil prices are down, banks are failing, and Duane's $12 million in debt. His wife Karla drinks too much, his children are always in trouble, and he tom-cats around with the wives of friends. Jacy's back in town, after a mildly successful acting career, life in Italy, and the death of her son. Folks assume Duane and Jacy will resume their high school romance. And Sonny is "tired in his mind," causing worries for his safety. Can these friends find equilibrium in middle age?.
IMDB Rating: 6.0
IMDB Votes: 3000
Genere: Drama, Romance
Country: USA
Duration: 126 min
Plot tags: independent film, crying, sentimental, touching, serious, realistic, light, road movie, feel good, unusual plot structure
Similar in 79%
Charlotte Sometimes (2002)
Plot Summary:
Michael, a young mechanic, is forced to choose between a daring tryst with an alluring stranger and the habitual comfort of his bittersweet obsession: his beautiful young roommate.
IMDB Rating: 6.3
IMDB Votes: 1000
Genere: Drama, Romance
Country: USA
Duration: 85 min
Plot tags: sincere, sexy, light, captivating, romantic, romantic drama, erotic, serious, realistic, contemplative
Similar in 80%
All the Real Girls (2003)
Plot Summary:
In a small North Carolina town, Paul, a womanizer, meets Noel, a confused intellectual returning home for the first time in years since she left for boarding school. The film depicts the typical romance of a good girl and a bad boy, in an interesting way.
IMDB Rating: 6.7
IMDB Votes: 11000
Genere: Drama, Romance
Country: USA
Duration: 108 min
Plot tags: romantic, sexy, melancholic, independent film, atmospheric, sincere, touching, contemplative, realistic, talky
Similar in 80%
Four Sheets to the Wind (2007)
Plot Summary:
After his father's untimely suicide, Cufe leaves his home in a Native American reservation in search of a more fulfilling life.
IMDB Rating: 6.2
IMDB Votes: 633
Genere: Drama, Romance
Country: USA
Duration: 81 min
Plot tags: sincere, touching, serious, realistic, romantic, romantic comedy, gloomy, crying
Similar in 86%
Ruby in Paradise (1993)
Plot Summary:
Reeling from her mother's recent death, Ruby Lee Gissing relocates to Florida to start anew. After finding a job at a souvenir store, Ruby becomes friends with the shop's owner, Mildred Chambers, and slowly acclimates to her new surroundings. Before long, she's juggling the affections of Mildred's Lothario son, Ricky, and the good-natured Mike. As she wavers between Ricky and Mike, Ruby also tries to come to terms with her past.
IMDB Rating: 6.9
IMDB Votes: 3000
Genere: Drama, Romance
Country: USA
Duration: 114 min
Plot tags: independent film, touching, realistic, road movie, mumblecore, romantic drama, psychological, tense, sentimental, sincere
Similar in 90%
Our Friend (2019)
Plot Summary:
After learning that his terminally ill wife has six months to live, a man welcomes the support of his best friend who moves into their home to help out.
IMDB Rating: 7.3
IMDB Votes: 15000
Genere: Drama, Romance
Country: USA
Duration: 124 min
Plot tags: sad, captivating, touching, family comedy, cult classic, entertaining
Similar in 80%
Moonlight Mile (2002)
Plot Summary:
As he copes with the death of his fiancee along with her parents, a young man must figure out what he wants out of life.
IMDB Rating: 6.6
IMDB Votes: 15000
Genere: Drama, Romance
Country: USA
Duration: 117 min
Plot tags: sentimental, emotional, realistic, clever, romantic, art film, romantic drama, serious, gloomy, crying
Similar in 86%
The Good Girl (2002)
Plot Summary:
A discount store clerk strikes up an affair with a stock boy who considers himself the incarnation of Holden Caulfield.
IMDB Rating: 6.4
IMDB Votes: 47000
Genere: Drama, Romance
Country: USA, Germany, Netherlands
Duration: 93 min
Plot tags: dark comedy, realistic, sincere, independent film, melancholic, disturbing, intense, humorous, semi serious, cult classic
Similar in 81%
St. Elmo's Fire (1985)
Plot Summary:
Seven friends - Alec, Billy, Jules, Kevin, Kirby, Leslie and Wendy - are trying to navigate through life and their friendships following college graduation. Alec, who aspires to political life, has just shown his true colors by changing his allegiance from Democrat to Republican, which freaks out girlfriend Leslie, who he wants to marry. Budding architect Leslie, on the other hand, has an independent streak. She believes she has to make a name for herself to find out who she is before she can truly commit to another person in marriage. But Leslie and Alec have decided to live together. Because Leslie refuses to marry Alec, he believes that justifies certain behavior. Kirby, who wants to become a lawyer and who pays for his schooling by working as a waiter at their local hangout called St. Elmo's Bar, and struggling writer Kevin are currently roommates. They are on opposite extremes of the romance spectrum.
IMDB Rating: 6.4
IMDB Votes: 45000
Genere: Drama, Romance
Country: USA
Duration: 110 min
Plot tags: sentimental, intense, sincere, serious, realistic, talky, cult classic, teen, retro, sexy
Similar in 81%
The Way We Were (1973)
Plot Summary:
Two desperate people have a wonderful romance, but their political views and convictions drive them apart.
IMDB Rating: 7.0
IMDB Votes: 27000
Genere: Drama, Romance
Country: USA
Duration: 118 min
Plot tags: intellectual, sentimental, realistic, serious, captivating, talky, intense, romantic, touching, sweet
Similar in 76%
Evening (2007)
Plot Summary:
As Constance (Natasha Richardson) and Nina (Toni Collette) gather at the deathbed of their mother, Ann (Vanessa Redgrave), they learn for the first time that their mother lived an entire other lifetime during one evening 50 years ago. In vivid flashbacks, the young Ann (Claire Daines) spends one night with a man named Harris (Patrick Wilson), who was the love of her life.
IMDB Rating: 6.4
IMDB Votes: 14000
Genere: Drama, Romance
Country: USA, Germany
Duration: 117 min
Plot tags: touching, emotional, sentimental, romantic, intense, realistic, heartbreaking, tear jerker, epic, cult classic
Similar in 82%
After the Rain (1999)
Plot Summary:
Steph, an Afrikaner, struggles with his past and heritage in the new South Africa. When his girlfriend befriends a black South African man called Vusisizwe trouble brews.
IMDB Rating: 5.9
IMDB Votes: 278
Genere: Drama, Romance
Country: South Africa, USA
Duration: 103 min
Plot tags: serious, realistic, crying, tragic
Similar in 78%
Personal Velocity (2002)
Plot Summary:
Three women's escapes from their afflicted lives. Each struggles to flee from the men who confine their personal freedom.
IMDB Rating: 6.5
IMDB Votes: 4000
Genere: Drama, Romance
Country: USA
Duration: 86 min
Plot tags: talky, stylized, intense, touching, psychological, sincere, serious, realistic, anthology, erotic
Similar in 76%
Heights (2005)
Plot Summary:
'Heights' follows five characters over 24 hours on a fall day in New York City. Isabel, a photographer, is having second thoughts about her upcoming marriage to Jonathan, a lawyer. On the same day, Isabel's mother Diana learns that her husband has a new lover and begins to re-think her life choices and her open marriage. Diana and Isabel's paths cross with Alec, a young actor, and with Peter, a journalist. As the interrelated stories proceed, the connections between the lives of the five characters begin to reveal themselves and their stories unravel. Isabel, Jonathan, Diana, Alec, and Peter must choose what kind of lives they will lead before the sun comes up on the next day.
IMDB Rating: 6.8
IMDB Votes: 5000
Genere: Drama, Romance
Country: USA
Duration: 93 min
Plot tags: realistic, stylized, serious, clever, witty, talky, emotional, non-linear, controversial, gloomy
Similar in 84%
New Life (2016)
Plot Summary:
Benjamin Morton's life changed forever the day he met the little girl next door. Ava was and always would be the girl of his dreams. From the innocence of a childhood friendship, through adolescent attraction, their love strengthens and grows. When life takes a turn neither of them expected, their entire future is called into question.
IMDB Rating: 6.1
IMDB Votes: 983
Genere: Drama, Romance
Country: USA
Duration: 88 min
Plot tags: romantic, sincere, rough, thought provoking, touching, captivating, christian film, independent film
Similar in 80%
Poetic Justice (1993)
Plot Summary:
In this film, we see the world through the eyes of main character Justice, a young African-American poet. A mail carrier invites a few friends along for a long overnight delivery run.
IMDB Rating: 6.1
IMDB Votes: 16000
Genere: Drama, Romance
Country: USA
Duration: 109 min
Plot tags: road movie, hood, touching, realistic, sentimental, sincere, serious, emotional, compassionate, erotic
Similar in 82%
Feast of Love (2007)
Plot Summary:
A meditation on love and its various incarnations, set within a community of friends in Oregon. It is described as an exploration of the magical, mysterious and sometimes painful incarnations of love.
IMDB Rating: 6.5
IMDB Votes: 17000
Genere: Drama, Romance
Country: USA
Duration: 97 min
Plot tags: touching, romantic, sentimental, semi serious, feel good, humorous, realistic, erotic, inspirational, emotional
Similar in 75%
We Don't Live Here Anymore (2004)
Plot Summary:
Married couple Jack and Terry Linden are experiencing a difficult period in their relationship. When Jack decides to step outside the marriage, he becomes involved with Edith, who happens to be the wife of his best friend and colleague, Hank Evans. Learning of their partners' infidelity, Terry and Hank engage in their own extramarital affair together. Now, both marriages and friendships are on the brink of collapse.
IMDB Rating: 6.3
IMDB Votes: 10000
Genere: Drama, Romance
Country: Canada, USA
Duration: 101 min
Plot tags: emotional, stylized, psychological, touching, sincere, contemplative, erotic, realistic, scary, sensual