Best movies like Windy City

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.

Two desperate people have a wonderful romance, but their political views and convictions drive them apart.

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.

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.

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.

A planned evening of debauchery in Las Vegas to celebrate their best friend's wedding goes horribly -- but hilariously -- wrong for five average guys.

Two young couples taste the "free and easy" life on a cross country motor-home tour until love backfires and tragedy follows.

When writer's block derails the literary dreams of Olly Pickering, he has to move in with his friend Murray after losing all his money. Things start to look up when Olly's college pal James asks him to be the best man at his wedding. Prior to the nuptials, Olly is drawn to a woman whom he thinks is the bride's sister -- only she turns out to be the bride, Sarah. Can Murray, who dislikes James, help get Sarah and Olly together?

Seven old college friends gather for a weekend reunion after the funeral of one of their own.

John Twiller takes down his high school yearbook and begins to reminiscence about that time he first moved into the neighborhood in 1956. His teenage self, Jack is obsessed with Lily one of the more popular girls around. The sole obstacle is Angelo, her bullying boyfriend. With the help of his pals Crutch, Floyd, and Spider, he makes every attempt possible to change her mind.

Annie's life is a mess. But when she finds out her lifetime best friend is engaged, she simply must serve as Lillian's maid of honor. Though lovelorn and broke, Annie bluffs her way through the expensive and bizarre rituals. With one chance to get it perfect, she’ll show Lillian and her bridesmaids just how far you’ll go for someone you love.

Friends since childhood, a magazine editor and a hip-hop record executive stumble into romantic territory.

Labor Day in a small Kansas farm town. Hal, a burly and resolute drifter, jumps off a dusty freight train car with the purpose of visiting Alan, a former college classmate and son of the richest man in town.

Weekend trips, office parties, late night conversations, drinking on the job, marriage pressure, biological clocks, holding eye contact a second too long… you know what makes the line between “friends” and “more than friends” really blurry? Beer.

A freelance illustrator in New York suffers a quarter-life crisis and leaves his home for the west coast.

Blue-collar Paulie prepares for fatherhood and his forthcoming wedding to Sue by hanging out with his groomsmen. Brother Jimbo, cousin Mike, and his pals fill the reunion with drinking, boys-will-be-boys antics and a few unexpected personal confessions. But, when the bonding devolves into accusations and regret, Paulie has to decide whether he's ready to tie the knot and take this big step into adulthood.

Lovelife is a 1997 romantic comedy film written and directed by Jon Harmon Feldman. The ensemble cast includes Matt Letscher, Sherilyn Fenn, Saffron Burrows, Carla Gugino, Bruce Davison, Jon Tenney and Peter Krause. Lovelife was nominated for a Feature Film Award at the 1997 Austin Film Festival, and won an Audience Award at the Los Angeles Independent Film Festival. The film was winner of the screenplay award at the L.A. Indie fest.

Two men from Pennsylvania give up hope in their small run down coal mining town, and head off in search of the beaches of California. The two steal cars as they travel across the USA and are joined by a wild young woman.

First of all, the title does not refer to someone sentenced to jail. It is a movie about 6 lifetime friends who are all hitting the big `3-0' together during the same year. Each one looks inside themselves to see where has my life gone and what am I going to do with my future. Actually, what I saw was a black Seinfeld comedy. Tracy Morgan, who is one of the main characters, is a struggling comedian just like Jerry Seinfeld. He gives his opinion of what women want in a man in one of his comedy routines. Melissa De Sousa is looking for a man before time runs out. She is just like Elaine in Seinfeld. I don't remember the big problem with turning thirty, however, all the characters in this movie can show you what they are, such as not having fame, riches, a husband, a thin body, and staying young. Their life stories are probably repeated many times around the world.

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?

Two strangers, whose paths are always crossing, finally meet when fate steps in. It took them twenty years to fall in love at first sight.

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.

After his father's untimely suicide, Cufe leaves his home in a Native American reservation in search of a more fulfilling life.

Mark Anderson, a recent stroke victim who is frail and weak. Also, his best friend Thomas, a classic over the hill drag queen desperate for love and happiness. Mark and Thomas have a master plan, to find Mark's son, James Anderson the love of his life once and for all.

When a group of old college friends reunite over a long weekend after one of them attempts suicide, old crushes and resentments shine light on their life decisions, and ultimately push friendships and relationships to the brink.

A group of guys who sang together in a college a cappella group reunite 15 years later to perform at a friend's wedding and discover how their lives have progressed -- and in some cases regressed -- since their college heyday.

An artist dumps her longtime boyfriend, but her attempt to take a break from dating ends when she quickly finds herself in two passionate romances.

Winning your childhood sweetheart can create more problems than it solves.

When Lacey takes a rare break from work for her friend Ava's Christmas Eve wedding, she reconnects with her former flame, Ean. The two decorate the cottage where the newlyweds will spend their honeymoon – a cottage said to bring true love to anyone who stays there – and feel their chemistry return.

Family friends Sam and Kat spend every Christmas Eve at the Children's Table. They grow up together, sharing the highs and lows of young adulthood. And at thirty, Sam realizes that Kat is the one... but he's afraid that the past will get in the way.

Jennifer and Kevin are childhood best friends who have lived together, platonically, as adults for many years. When Jennifer decides to marry her cheating, manipulative boyfriend, Bryce Kevin has to stop the wedding to protect her from making, what he believes is, a terrible mistake. With a little help from his brother and neighbor Kevin discovers that he and Jennifer are already legally married due to common law, having lived together for seven years and, as such, Jennifer can not marry Bryce.

A woman is determined to stop the wedding of her best friend, since she has been secretly in love with him.

It's always a good day for a funeral at St. Mark's Middle School. Andy and Charlie, two altar servers, don't just get to miss class anytime a parishioner kicks the bucket, they cut out early and play hooky as soon as the service is over. Eventually their irreverent personalities will put them in a situation that is too big for them to handle.

Jed prepares to interview French cineaste and self-appointed expert on the nature of love - Thierry Grimandi. The worldly and somewhat jaded Jed is dead-set on dismissing the auteur's musings as pompous and, well French, until his own relationship with Cheryl starts to fall apart and he is forced to re-evaluate the illusive subject. Soon everyone is talking about love: his relationship counsellor, drinking buddy Marcus and Marcus' girlfriend Sophie Beginnings, endings, tricks...could the French be on to something?

A New York stockbroker introduces a girlfriend to his buddy from out of town, then regrets it.