Binge Best Chicago TV Shows on HBO Max Now!

Chicago TV shows on HBO Max offer a captivating glimpse into the vibrant and diverse life of one of America's biggest cities. These dramas and comedies often delve into the rich cultural tapestry and complex social dynamics that define Chicago. By exploring themes of crime, justice, politics, and community, these shows bring to life the multifaceted human experiences that make the city so unique. The urban backdrop serves as more than just scenery; it's an integral part of the stories, providing an authentic and gritty setting that amplifies the narratives. The type of TV shows available in this genre ranges from intense crime dramas to light-hearted comedies, each offering a different perspective on Chicago's life. Characters typically seen in these shows often include dedicated police officers, ambitious politicians, struggling families, and quirky neighborhood locals.

Mavis! (HBO)

Mavis! (HBO)
Insightful documentary on singer Mavis Staples' career

Released: 2016

Platform: Max

Rating: TV-14

Run time:

Cast

Mavis! is a must-watch documentary for music enthusiasts and fans of inspiring personal stories. Directed by Jessica Edwards and released by HBO in 2016, this film offers an intimate glimpse into the life and career of the legendary gospel, soul, and R&B singer Mavis Staples. From her early days with The Staple Singers to her impactful solo career, Mavis journey is one of resilience, talent, and profound influence on both music and social activism. The documentary is enriched by interviews with iconic musicians like Bob Dylan and Jeff Tweedy, who shed light on Mavis' enduring legacy. Featuring soul-stirring live performances, Mavis! not only showcases her musical genius but also her vibrant, magnetic personality. Whether you're a longtime fan or a newcomer, this film’s emotional depth and musical prowess make it an essential and compelling watch.

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Family Matters

Family Matters
Wholesome sitcom focused on Winslow family life

Released: 1989

Platform: Max

Rating: TV-G

Run time: 9 Seasons Available (215 Episodes)

Cast
Jaleel White, Reginald Veljohnson, Joe Payton, Rosetta Lenoire, Darius Mccrary, Kellie Williams

Family Matters is a classic American sitcom that ran from 1989 to 1998, chronicling the lives of the Winslow family, a middle-class African American family in Chicago. Created by William Bickley and Michael Warren, the show is notable for its long run and diverse cast, breaking television norms of the time. With compelling characters like Reginald VelJohnsons Carl Winslow and JoMarie Paytons Harriette Winslow, the series provides a mix of heartfelt family moments and comedic brilliance. However, what truly sets Family Matters apart is Jaleel White’s portrayal of Steve Urkel—a character intended as a guest but who became a cultural phenomenon. Urkel's quirky humor and catchphrases like Did I do that? brought unique charm to the show. Filled with memorable quotes, crossover episodes, and an undeniably catchy theme song, Family Matters is a must-watch for its blend of family values, humor, and groundbreaking representation.

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The Janes (HBO)

The Janes (HBO)
All-female spy team battles international threats

Released: 2022

Platform: Max

Rating: TV-MA

Run time:

Cast
Heather Booth, Judith Arcana, Marie Leaner, Diane Stevens, Eleanor Oliver

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South Side

South Side
Comedic portrayal of life in South Chicago

Released: 2019

Platform: Max

Rating: TV-MA

Run time: 3 Seasons Available (28 Episodes)

Cast
Sultan Salahuddin, Kareme Young, Michael Brunlieb, Ronald Conner, Aaron Heart, Lanre Idewu, Langston Kerman, Antoine Mckay, Will Miles, Diallo Riddle, Chandra Russell, Bashir Salahuddin, Zuri Salahuddin, Rashawn Scott, Nefetari Spencer, Edward Williams, Quincy Young, Sultan Salahuddin, Kareme Young, Quincy Young, Chandra Russell, Bashir Salahuddin, Zuri Salahuddin

South Side, an American comedy series that first aired on Comedy Central in July 2019, immerses viewers in the vibrant, challenging life of Chicagos Englewood neighborhood. Following the comedic and heartfelt journeys of best friends Simon James and Kareme Young, this show offers a refreshing escape from stereotypes, showcasing their struggle and ambition as they navigate their post-graduation world while working at Rent-T-Own. Created by Diallo Riddle, Bashir Salahuddin, and Sultan Salahuddin, the series is celebrated for its authentic representation, having been filmed on location in Chicago. The humor is elevated by stellar performances from Sultan Salahuddin, Kareme Young, and Chandra Russell, who breathe life into their characters with charismatic ease. The series sharp writing, diverse soundtrack, and compelling quotes make it a must-watch for anyone seeking a genuine, humorous, and inspiring depiction of inner-city life and entrepreneurial spirit.

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Windy City Rehab

Windy City Rehab
Chicago home renovations by designer Alison Victoria

Released: 2017

Platform: Max

Rating: TV-PG

Run time: 4 Seasons Available (32 Episodes)

Cast
Alison Victoria, Donovan Eckhardt

Windy City Rehab is an enthralling HGTV series that immerses viewers in the art of home restoration in Chicagos historic neighborhoods. Premiered in 2017, the show stars the dynamic duo of Alison Victoria, a passionate interior designer, and Donovan Eckhardt, an exceptional construction manager. Together, they tackle dilapidated properties, overcoming hurdles like strict permits and construction delays to transform these homes into breathtaking modern spaces while honoring their original architectural charm. Produced by Big Table Media, the compelling transformations are a testament to the duos dedication and skill, offering not only aesthetic beauty but also practical living spaces. Why Watch? The series is a must-watch for anyone who loves home makeovers, appreciates historic preservation, or enjoys seeing the immense challenges and rewards of real estate development. Alison and Donovan's commitment and eye for detail ensure every episode is packed with inspiration, drama, and stunning reveals, making it a captivating watch for design enthusiasts and casual viewers alike.

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The Front Page

The Front Page
A classic comedy about newspaper reporting chaos

Released: 1931

Platform: Max

Rating: TV-G

Run time:

Cast
Adolphe Menjou, Pat O'Brien, Mary Brian, Glen Macwilliams

The Front Page (1931) is a must-watch for film enthusiasts and those intrigued by the classic era of cinema. Directed by Lewis Milestone and produced by Howard Hughes, this pre-code comedy-drama masterfully explores the turbulent world of early 20th-century journalism. Its fast-paced plot, sharp dialogue, and innovative overlapping conversations provide a compelling glimpse into the high-stakes, morally ambiguous life of newspaper reporters. With standout performances by Adolphe Menjou as the editor Walter Burns, and Pat OBrien as the conflicted reporter Hildy Johnson, the film captures the intense dynamics and ethical dilemmas of the newsroom. Despite its initial commercial struggles, its critical acclaim and subsequent rediscovery highlight its timeless impact. Accompanied by Alfred Newmans evocative score, The Front Page remains influential, inspiring notable remakes like His Girl Friday. Dive into this cinematic gem for a piece of film history that still resonates with modern audiences.

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Social Confrontation: The Battle of Michigan Avenue

Social Confrontation: The Battle of Michigan Avenue
Documentary illustrating 1968's fierce political protests

Released: 1968

Platform: Max

Rating: TV-PG

Run time:

Cast

Social Confrontation: The Battle of Michigan Avenue is a pivotal documentary that provides a raw and unfiltered glimpse into the tumultuous events of the 1968 Democratic National Convention. By intertwining real-life footage of National Guardsmen clashing with anti-Vietnam War protestors, the film doesnt just recount history; it immerses viewers in the fervent atmosphere of the era. Mayor Daleys intense stand against the protestors and the mass arrests near Grant Park highlight the eras social and political tensions, providing invaluable insights into anti-war sentiments and their impact on American politics. Rich with authentic sounds and spontaneous chants, the documentary delivers an unvarnished narrative thats both compelling and educational. Although it has not garnered formal awards, its candid portrayal makes it an essential watch for those interested in understanding the complexities of civil unrest and government response. This film is a powerful reminder of the past and a crucial learning tool for the present.

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Mike & Molly

Mike & Molly
Overweight couple navigates love and life together

Released: 2010

Platform: Max

Rating: TV-14

Run time: 6 Seasons Available (127 Episodes)

Cast
Billy Gardell, Melissa McCarthy, Reno Wilson, Katy Mixon, Nyambi Nyambi, Swoosie Kurtz, Louis Mustillo, Cleo King, Rondi Reed, Billy Gardell, Melissa McCarthy, Reno Wilson, Katy Mixon, Nyambi Nyambi, Swoosie Kurtz

Mike & Molly (2010-2016) is an endearing American sitcom that follows the charming love story of Chicago police officer Mike Biggs and elementary school teacher Molly Flynn, who meet at an Overeaters Anonymous group. Created by Mark Roberts and produced by comedy legend Chuck Lorre, this show artfully balances humor and romance while tackling sensitive topics like overeating and dieting. Featuring standout performances by Billy Gardell and Melissa McCarthy, the series also stars Reno Wilson and Katy Mixon, adding depth and plenty of laughs. Melissa McCarthys role earned her a Primetime Emmy in 2011. The shows relatable characters, witty dialogue, and heartwarming moments, set against a delightful soundtrack, make it a must-watch for anyone who appreciates smart, heartfelt comedy.

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American Revolution 2

American Revolution 2
Insightful documentary detailing Chicago's racial tensions

Released: 1969

Platform: Max

Rating: TV-14

Run time:

Cast

American Revolution 2, a compelling documentary released in 1969, delves into the socio-political unrest surrounding the 1968 Democratic Convention protest and riot. Co-directed by Howard Alk and Mike Gray, the film offers a raw, real-time perspective on the struggles of working-class African Americans in Chicago, the initiatives of the Black Panther Party, and the plight of impoverished Southern white youths. Unlike mainstream Hollywood productions, this documentary provides an authentic glimpse into the racial and class inequalities of the time, making it a critical historical resource. The films genuine footage and real-life sounds offer an engaging and educational experience, immersing viewers in the gritty reality of the late 60s. Watching American Revolution 2 is essential for those seeking to understand the complex social issues that have shaped modern American society.

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Native Son (HBO)

Native Son (HBO)
African-American man's life spirals after wealthy employment

Released: 2019

Platform: Max

Rating: TV-MA

Run time:

Cast
Ashton Sanders, Margaret Qualley, Nick Robinson, Kiki Layne, Elizabeth Marvel, David Alan Grier, Bill Camp, Sanaa Lathan

Native Son is a gripping film adaptation of Richard Wrights seminal novel, vividly brought to life on HBO. Directed by Rashid Johnson in his impressive debut and featuring a screenplay by Suzan-Lori Parks, the film immerses viewers in the life of Bigger Thomas, a young African-American navigating a racially charged 1930s Chicago. Ashton Sanders shines in the lead role, delivering a powerful portrayal riddled with tension and desperation. The supporting cast, including Margaret Qualley, Nick Robinson, and Elizabeth Marvel, provide nuanced and compelling performances. Set against an authentically captured Chicago backdrop, Native Son skillfully explores profound themes of race, class, and societal pressure. The evocative score by Kyle Dixon further enriches the film, blending classical and contemporary sounds to heighten emotional depth. This movie not only stays true to its literary roots but also offers a profound, relevant commentary on systemic issues, making it essential viewing for those interested in powerful storytelling and social justice.

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Single Long (HBO)

Single Long (HBO)
Exploring love and life in modern Shanghai

Released: 2012

Platform: Max

Rating: TV-MA

Run time: 1 Seasons Available (7 Episodes)

Cast
Jack Lawrence Mayer, Sarra Jahedi, Ed Hausman, Mitch Salm, Brandon Ruiter, Cate Freedman, Irene Marquette, Johanna Middleton, Martine Moore, Sean Bolger

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ER

ER
Heart-pounding drama in a fast-paced hospital

Released: 1994

Platform: Max

Rating: TV-14

Run time: 15 Seasons Available (332 Episodes)

Cast
Anthony Edwards, George Clooney, Noah Wyle, Julianna Margulies, Gloria Reuben, Laura Innes, Maria Bello, Alex Kinston, Kellie Martin, Paul McCrane, Goran Visnjic, Maura Tierney, Michael Michele, Erik Palladino, Sherry Stringfield, Ming-Na Wen, Sharif Atkins, Mekhi Phifer, Linda Cardellini, Parminder Nagra, Eriq La Salle, Shane West, Scott Grimes, Michael Crichton, Anthony Edwards, George Clooney, Noah Wyle, Julianna Margulies, Gloria Reuben, Laura Innes

ER (1994-2009) is a must-watch for fans of gripping drama and realistic portrayals of the medical field. This trailblazing series, which aired for 15 seasons, masterfully combines fast-paced medical action with deeply emotional personal storylines, depicting the harrowing life-and-death battles faced by the doctors and nurses at Chicagos County General Hospital. Produced by industry giants like Warner Bros. Television, the show uses innovative hand-held camera techniques to immerse viewers in the frenetic energy of an emergency room. Featuring stellar performances from actors like Anthony Edwards, George Clooney, Noah Wyle, and Juliana Margulies, ER captures the professional and personal challenges of its characters with heartfelt authenticity. Enriched with a soundtrack that includes James Newton Howards iconic theme, the series offers both intensity and relatability. With its numerous accolades, including 22 Primetime Emmys and a Peabody Award, ER remains a landmark in television history, making it an unmissable experience for any viewer.

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Windy City Rehab: Alison's Dream Home

Windy City Rehab: Alison's Dream Home
Transforming Chicago's rundown spaces into dream homes

Released: 2023

Platform: Max

Rating: TV-G

Run time: 1 Seasons Available (3 Episodes)

Cast
Alison Victoria

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Cicero March

Cicero March
Civil Rights movement documentation in Chicago

Released: 1966

Platform: Max

Rating: TV-PG

Run time:

Cast
Mike Shea, Mike Gray, Jay Lifkin, Robert Lucas

Cicero March, released in 1966, is a gripping short film that offers a raw and authentic portrayal of the Chicago Civil Rights March. Capturing the intense passion, unwavering loyalty, and courageous determination of the participants, this documentary provides an unfiltered glimpse into the fight to end racial discrimination in 1960s Chicago. Shot in black and white and using low-tech equipment, the filmmakers convey a powerful sense of reality that makes the historical events resonate deeply. Though it did not win notable awards, Cicero March is celebrated for its historical importance and authentic depiction of the civil rights movement. Featuring the iconic anthem We Shall Overcome, this film is not just about a march but a pivotal struggle for freedom and equality. Watching Cicero March is essential to understanding the resilience and courage that fueled the civil rights movement, making it a must-see for anyone interested in social justice and American history.

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About This Collection

Chicago TV dramas and comedies on HBO Max.

Discover the best Chicago TV shows on HBO Max, featuring gripping dramas and thrilling crime series set in the Windy City. With diverse stories and iconic backdrops, Chicago TV shows on HBO Max offer an immersive experience into the heart of urban life and local culture.

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