Best Comedy Shows in Chicago

Chicago’s Comedy Scene: Top Picks for 2024/2025. Unveiling the Best in Comedy!
Prepare to embark on a journey through laughter and wit as we reveal the most acclaimed comedy shows and comedians this season. Dive into the vibrant world of stand-up comedy, improvisational masters, and captivating comedic talents currently touring. Secure your tickets now and be part of the exhilarating comedy nights in Chicago. Join us in celebrating the artists who make laughter the best medicine.

Contents

Top 30 Comedy Shows

Experience the pinnacle of comedic talent with our list of the 30 Funniest Comedians performing in Chicago, IL, this season.
# Comedy Shows
Venue Shows
Prices
1 Sleeping Village
60618, 3734 W Belmont Ave, Chicago, IL, US
1
Tickets from: $143
2 The Blackout Cabaret at Second City - Chicago
60614, 230 W. North Ave, Chicago, IL, US
1
Tickets from: $128
3 The Blackout Cabaret at Second City - Chicago
60614, 230 W. North Ave, Chicago, IL, US
1
Tickets from: $128
4 Mainstage at Second City - Chicago
60614, 1616 N. Wells St., Chicago, IL, US
8
Tickets from: $119
5 The Blackout Cabaret at Second City - Chicago
60614, 230 W. North Ave, Chicago, IL, US
1
Tickets from: $115
6 The Blackout Cabaret at Second City - Chicago
60614, 230 W. North Ave, Chicago, IL, US
14
Tickets from: $114
7 The Blackout Cabaret at Second City - Chicago
60614, 230 W. North Ave, Chicago, IL, US
1
Tickets from: $110
8 Chicago Improv
60173, 5 Woodfield Rd Woodfield Mall Store K120B, Schaumburg, IL, US
5
Tickets from: $107
9 Judy's Beat Lounge at Second City - Chicago
60614, 230 W. North Ave, Chicago, IL, US
6
Tickets from: $96
10 Judy's Beat Lounge at Second City - Chicago
60614, 230 W. North Ave, Chicago, IL, US
12
Tickets from: $93
11 e.t.c. Theater at Second City - Chicago
60614, 230 W. North Ave, Chicago, IL, US
39
Tickets from: $91
12 Donny's Skybox Theatre at Second City - Chicago
60614, 230 W. North Ave, Chicago, IL, US
6
Tickets from: $90
13 Rosemont Theatre
60018, 5400 North River Road, Rosemont, IL, US
8
Tickets from: $88
14 UP Comedy Club at Second City - Chicago
60614, 230 W. North Ave, Chicago, IL, US
12
Tickets from: $86
15 Mainstage at Second City - Chicago
60614, 1616 N. Wells St., Chicago, IL, US
3
Tickets from: $83
16 City Winery - Chicago
60607, 1200 W. Randolph St., Chicago, IL, US
7
Tickets from: $82
17 Donny's Skybox Theatre at Second City - Chicago
60614, 230 W. North Ave, Chicago, IL, US
5
Tickets from: $82
18 Lincoln Hall
60614, 2424 N. Lincoln Avenue, Chicago, IL, US
2
Tickets from: $78
19 City Winery - Chicago
60607, 1200 W. Randolph St., Chicago, IL, US
5
Tickets from: $78
20 Judy's Beat Lounge at Second City - Chicago
60614, 230 W. North Ave, Chicago, IL, US
7
Tickets from: $75
21 e.t.c. Theater at Second City - Chicago
60614, 230 W. North Ave, Chicago, IL, US
17
Tickets from: $73
22 Rosemont Theatre
60018, 5400 North River Road, Rosemont, IL, US
15
Tickets from: $73
23 Cubby Bear
60613, 1059 W. Addison, Chicago, IL, US
1
Tickets from: $72
24 Mainstage at Second City - Chicago
60614, 1616 N. Wells St., Chicago, IL, US
13
Tickets from: $72
25 Cubby Bear
60613, 1059 W. Addison, Chicago, IL, US
1
Tickets from: $71
26 Judy's Beat Lounge at Second City - Chicago
60614, 230 W. North Ave, Chicago, IL, US
8
Tickets from: $71
27 Copernicus Center
60630, 5216 West Lawrence Avenue, Chicago, IL, US
5
Tickets from: $62
28 Chicago Improv
60173, 5 Woodfield Rd Woodfield Mall Store K120B, Schaumburg, IL, US
73
Tickets from: $60
29 Vic Theatre
60657, 3145 N Sheffield, Chicago, IL, US
4
Tickets from: $60
30 Chicago Improv
60173, 5 Woodfield Rd Woodfield Mall Store K120B, Schaumburg, IL, US
10
Tickets from: $59
Show More

Overview Of Shows & Comedians

  • Shane Gillis is a stand-up comedian and actor recognized for his straightforward and sometimes contentious style of comedy. He came into the spotlight in 2019 when he was cast in “Saturday Night Live,” only to be dismissed shortly afterward following the surfacing of his previous racist and homophobic comments. Despite these controversies, Gillis continues to tour nationally, performing stand-up that frequently touches on themes like race, societal issues, and personal experiences, demonstrating his bold and unreserved comedic style.
  • I Think You Should Leave with Tim Robinson is a sketch comedy series available on Netflix, both created and performed by Tim Robinson, who previously worked on “Saturday Night Live.” The show is celebrated for its wildly absurd and quirky sketches that typically take unexpected, often outlandish turns, combining discomfort with uproarious laughter. The comedy is distinctively marked by its portrayal of awkward social scenarios, exaggerated characters, and a special mix of cringe-worthy moments and physical comedy, earning it a dedicated following among lovers of unconventional humor.
  • Matt Rife, a vibrant young stand-up comedian and actor, first came into the spotlight through MTV’s “Wild ‘N Out.” Renowned for his engaging stage presence and humor that resonates well with audiences, Rife incorporates themes from his personal life, relationships, and elements of youth culture into his routines. His comedic talent has been showcased across a variety of platforms and television shows, including notable appearances on “Brooklyn Nine-Nine” and “The Challenge,” demonstrating his adaptability in both comedy and acting.
  • Sebastian Maniscalco is celebrated for his dynamic stand-up comedy, marked by animated delivery and sharp insights into daily life, heavily influenced by his Italian-American background. His routines frequently explore the quirks of social interactions, family dynamics, and everyday scenarios, all presented with a vibrant flair that includes notable physical comedy and expressive facial gestures. Maniscalco’s work has led to several acclaimed comedy specials, and he has also made significant contributions to film and television, showcasing his broad appeal and comedic talent.
  • Jeff Arcuri is a rising comedian celebrated for his smart writing and approachable stage presence. Drawing inspiration from his own life, Arcuri’s comedy resonates with audiences through its relatability and explores themes ranging from dating to everyday occurrences. He has appeared on “The Late Show with Stephen Colbert” and has carved out a niche for himself on the comedy festival scene. Arcuri’s engaging style and humorous perspective allow him to connect effortlessly with a wide array of audiences, highlighting his growing influence in the comedy world.
  • Mike Epps is a seasoned stand-up comedian and actor whose career has flourished over more than two decades. Initially rising to prominence through the Def Comedy Jam series, Epps has since taken on roles in a wide array of films and television shows. His comedic style uniquely combines observational humor, incisive wit, and personal anecdotes, often addressing topics like race, family dynamics, and socio-economic challenges. Epps’ dynamic stage presence and his skill in character portrayal have endeared him to audiences, cementing his status as a cherished personality in both the realms of stand-up comedy and acting.
  • Semyon Slepakov is a prominent Russian comedian, singer-songwriter, and television producer known for his satirical take on contemporary Russian life. His humor often revolves around social and political issues in Russia, delivered through comedic songs and sketches that have garnered him a vast following in the Russian-speaking world. Slepakov is also known for his work on popular Russian TV shows and series, where his talent for satire shines through, making him a significant figure in Russian comedy and entertainment.
  • Nate Bargatze is a celebrated American stand-up comedian known for his relaxed style and understated delivery. His comedy distinctively features clean, observational humor, often highlighting everyday quirks, family dynamics, and aspects of his Southern background. Bargatze excels at transforming ordinary situations into engaging, humorous narratives that audiences find both relatable and amusing. He has appeared in several stand-up specials and late-night TV shows, gaining recognition for his distinctive comedic approach and impeccable timing.
  • La India Yuridia is a celebrated Mexican comedian who humorously addresses everyday challenges, gender roles, and relationships through the lens of a Mexican woman. Her comedic persona, which cleverly satirizes traditional Mexican stereotypes, enables her to tackle a variety of social issues with both humor and depth. Her performances are particularly resonant, connecting deeply with audiences by reflecting shared experiences common to many in Mexican and broader Latin American communities.
  • The Best Of The Second City  showcases top sketches and performances from the esteemed history of The Second City, a legendary improv comedy troupe based in Chicago. Renowned as a breeding ground for celebrated comedians and actors, these “Best Of” shows blend iconic sketches with new material, all performed by current members of the troupe. The performances encapsulate the troupe’s hallmark improvisational and sketch comedy style, which has significantly influenced generations of comedic talent.
  • Franco Escamilla is a Mexican stand-up comedian and musician known for his dark humor and biting wit. His comedy often explores personal experiences, social norms, and cultural peculiarities, frequently touching on themes relevant to Mexican society and beyond. Escamilla’s global appeal has grown through his specials and international tours, making him one of the most recognized figures in Spanish-language comedy.
  • Bert Kreischer is an American stand-up comedian, actor, and reality TV host renowned for his vivid storytelling and exuberant personality. Known for performing shirtless, Kreischer draws heavily from his life, including his party-centric lifestyle, family dynamics, and various escapades. He is particularly famous for a collegiate anecdote believed to have inspired the movie “Van Wilder.” Kreischer’s boundless energy and embrace of the absurd have cemented his popularity, leading to multiple comedy specials and podcasts.
  • Brincos Dieras the stage name of Juan Carlos Escalante, is a Mexican stand-up comedian celebrated for his unique comedic approach that skillfully combines social commentary with personal anecdotes. His stage name, a twist on a common Mexican expression of disbelief, aptly mirrors his knack for catching audiences off guard with incisive observations and sharp wit. Escalante’s comedy often explores the intricacies of everyday life in Mexico, relationship dynamics, and social challenges, all infused with his distinctive humor and satirical edge.
  • Bill Burr is an American stand-up comedian, actor, and podcaster celebrated for his sharp wit and candid style. Known for his comedic rants and insightful observations on society, politics, and gender relations, Burr’s humor typically skewers societal norms and personal experiences with a direct and unfiltered approach. This style has earned him a substantial following. Burr’s talents extend to television and film, including memorable roles in “Breaking Bad” and as both co-creator and star of the animated series “F Is for Family.” His unique blend of cynicism and charisma makes his comedy not only relatable but also deeply engaging.
  • Wanda Sykes is a known comedian, actress, and writer known for her sharp humor and fearless demeanor. In her stand-up routines, she covers an array of subjects ranging from politics and societal issues to race and her own experiences, as an American lesbian. Sykes has received praise for her work in television, film and live comedy for her ability to approach topics with both wit and sensitivity. She has also taken on roles in TV shows and movies while also making a name for herself as a writer on “The Chris Rock Show.” Through her entertainment contributions, she does not entertain audiences. Also encourages meaningful discussions establishing herself as a respected figure, in the entertainment realm.
  • Daz Games is a popular gaming and entertainment channel on YouTube, managed by Darren Black, a British YouTuber and comedian. The channel is best known for the “Daz Watches” series, where Darren reacts humorously and incredulously to various internet videos. “Daz Games Live” encompasses live streaming events or performances that are extensions of the channel’s regular content. Darren’s videos effectively mix gaming, comedic commentary, and social observation, making his channel a lively and engaging platform for viewers. His distinct charm and sharp comedic timing have garnered a loyal audience, establishing a strong presence on social media platforms.
  • Impractical Jokers Live showcases the live performances of The Tenderloins, the comedy troupe behind the hit hidden-camera show “Impractical Jokers.” These live events blend stand-up comedy, behind-the-scenes stories, and live versions of the challenges fans love from the TV show. The unique chemistry and improvisational skills of the group make each performance a dynamic and engaging experience for the audience, offering a deeper dive into the antics and camaraderie that have made their television series a favorite. This interactive show allows fans to experience the humor and spontaneity of the Jokers in a live setting, extending the fun beyond the screen.
  • Sofía Niño de Rivera is a celebrated Mexican stand-up comedian distinguished by her incisive wit and keen observational comedy. Her routines often tackle subjects such as Mexican society, politics, and gender issues, all infused with a distinct humor that resonates broadly. Sofía rose to prominence with her acclaimed Netflix specials, marking her as one of the first Latin American comedians to be featured on the platform. Her forthright delivery and skill in addressing intricate topics humorously have cemented her status as a pivotal figure in both the Mexican and international comedy scenes.
  • Kevin James is an American actor and stand-up comedian known for his everyman appeal and generous humor. He first gained widespread fame as the star of the hit television sitcom “The King of Queens,” where he played Doug Heffernan, a lovable delivery driver with a sharp wit. James’ comedy often revolves around his observations on everyday life, relationships, and his experiences as a husband and father. In addition to his work on television, James has appeared in several films and has released stand-up specials that showcase his relatable style of humor and charismatic stage presence.
  • Chelsea Handler is a renowned American comedian, actress, television host, and author, celebrated for her forthright humor and incisive commentary on societal and political matters. She rose to prominence as the host of the late-night talk show “Chelsea Lately,” which aired on E! from 2007 to 2014, noted for her irreverent interview style and dynamic roundtable discussions with celebrities and comedians. Handler’s comedy sharply addresses themes like relationships, sexuality, and personal anecdotes, often served with a candid and unfiltered perspective. She is also a successful author with several bestsellers to her name and has been involved in numerous projects on television and Netflix, further solidifying her footprint in the entertainment industry.
  • Ali Wong is an American stand-up comedian, actress, and writer known for her edgy and candid comedy that often explores themes of marriage, motherhood, and her experiences as an Asian American woman. Wong gained significant acclaim for her Netflix stand-up specials “Baby Cobra” and “Hard Knock Wife,” performed while visibly pregnant, challenging stereotypes about women in comedy. Her humor is characterized by its boldness and honesty, and she has become a prominent voice in the comedy world for her ability to tackle taboo subjects with wit and humor.
  • Ten Dollar Comedy might refer to a comedy show, series, or venue known for offering live comedy performances at an affordable price, likely aiming to make comedy more accessible to a broader audience. Such events often feature a lineup of emerging and established comedians, providing a platform for diverse comedic voices and styles. These shows can be an excellent way for comedy fans to discover new talent and enjoy an evening of entertainment without a significant financial commitment.
  • America Runs on Women could be a slogan or title associated with a comedy special, series, or event that celebrates and showcases female comedians. This concept likely emphasizes the contributions of women to the comedy industry and society at large, offering a platform for female voices in comedy to share their unique perspectives, experiences, and humor. Such an event or series would highlight women’s diversity and talent in comedy, potentially featuring stand-up performances, sketches, and comedic commentary on various topics.
  • Marc Maron, an American comedian, podcaster, writer, and actor, is celebrated for his introspective and self-reflective style of comedy. He delves into themes such as personal life struggles, relationships, and the intricacies of modern life, which he presents with a mix of cynicism and vulnerability. Maron rose to fame with his influential podcast, “WTF with Marc Maron,” where he engages in deep, revealing interviews with a diverse array of cultural figures, including comedians, actors, and musicians. His skilled conversational ability helps him connect deeply with both his guests and listeners, earning him a distinguished place in the comedy landscape. Maron has also made notable appearances in several films and TV shows, most prominently in his semi-autobiographical series “Maron,” further showcasing his versatile talent.
  • Leanne Morgan is an American stand-up comedian celebrated for her distinctive Southern charm and relatable comedy. She crafts her humor from her everyday experiences as a wife, mother, and woman, delivering anecdotes with warmth and a sharp wit. Morgan’s stand-up resonates with a broad audience, especially those who value comedy rooted in real-life situations and family dynamics. She has built a substantial following through her comedy tours, television appearances, and an active presence on social media, where she often shares funny insights into daily life, endearing herself to fans with her down-to-earth perspective and engaging storytelling.
  • Mike Birbiglia is an American comedian, actor, writer, and director celebrated for his distinctive approach to storytelling in comedy. His stand-up routines are marked by their long-form narratives that skillfully blend humor with poignant personal reflections, tackling subjects like health, relationships, and life’s various absurdities. Birbiglia excels at transforming personal challenges and socially awkward moments into engaging comedic tales. Additionally, he is renowned for his off-Broadway shows and several comedy specials. His feature films, such as “Sleepwalk with Me” and “Don’t Think Twice,” are heavily inspired by his own experiences and stand-up performances, further showcasing his depth as a storyteller and entertainer.
  • Hannah Berner is a comedian, podcast host, and former reality TV star known for her stint on Bravo’s “Summer House.” Berner’s comedy often touches on dating, social media, and millennial culture, delivered with a sharp wit and a candid, relatable approach. She hosts the popular podcast “Berning In Hell,” where she interviews guests about their insecurities, fears, and anxieties, showcasing her ability to blend humor with deeper conversations. Berner’s comedic style is marked by its modern sensibilities and her engaging, charismatic delivery.
  • Juanpis González is a fictional character created and portrayed by Colombian comedian Alejandro Riaño. This character is a satirical representation of the Colombian elite, known for his exaggerated and outlandish behavior that highlights social inequalities and cultural idiosyncrasies within Colombian society. Through Juanpis González, Riaño delivers sharp social commentary and humor, addressing issues of class, politics, and lifestyle among Colombia’s upper class. The character has gained significant popularity in Colombia and among Spanish-speaking audiences for its biting humor and cultural critique.
  • Michael Blackson is a Ghanaian-American stand-up comedian and actor celebrated for his vibrant humor and distinctive perspective, heavily influenced by his African heritage and his experiences as an immigrant in the United States. Blackson is recognized for his unique delivery style, his eye-catching and colorful attire, and his knack for humorously exploring cultural differences and everyday situations. He has been featured in a variety of films, stand-up specials, and television shows, where his exuberant personality and comedic skills have endeared him to audiences worldwide.
  • Michelle Collins is an American comedian, television host, and personality renowned for her sharp wit and deep understanding of pop culture. Collins has served as a co-host on “The View” and has participated in a variety of television projects, podcasts, and live comedy shows. Her comedic style frequently focuses on celebrity culture, reality TV, and everyday peculiarities, all presented with her straightforward and humorous viewpoint. Known for her ability to spontaneously comment on current events with an engaging and conversational approach, Collins has carved out a notable presence in the entertainment world.

Comedy Venues

Discover Comedy Clubs and Venues in Chicago, IL
Allstate Arena
location 60018, 6920 Mannheim Road, Rosemont, IL, US
Upcoming Shows: 43
Athenaeum Theatre - IL
location 60657, 2936 North Southport Avenue, Chicago, IL, US
Upcoming Shows: 8
Auditorium Theatre - IL
location 60605, 50 East Congress Parkway, Chicago, IL, US
Upcoming Shows: 33
Buddy Guys Legends
location 60605, 754 S Wabash, Chicago, IL, US
Upcoming Shows: 19
Center Theatre At North Shore Center For The Performing Arts
location 60077, 9501 North Skokie Boulevard, Skokie, IL, US
Upcoming Shows: 40
CG's Comedy Club
location 60440, 619 E. Boughton Road Ste. 125, Bolingbrook, IL, US
Upcoming Shows: 4
Chicago Improv
location 60173, 5 Woodfield Rd Woodfield Mall Store K120B, Schaumburg, IL, US
Upcoming Shows: 66
CIBC Theatre
location 60603, 18 West Monroe Street, Chicago, IL, US
Upcoming Shows: 31
City Winery - Chicago
location 60607, 1200 W. Randolph St., Chicago, IL, US
Upcoming Shows: 70
Copernicus Center
location 60630, 5216 West Lawrence Avenue, Chicago, IL, US
Upcoming Shows: 10
Cubby Bear
location 60613, 1059 W. Addison, Chicago, IL, US
Upcoming Shows: 8
Des Plaines Theatre
location 60016, 1476 Miner St, Des Plaines, IL, US
Upcoming Shows: 37
Donny's Skybox Theatre at Second City - Chicago
location 60614, 230 W. North Ave, Chicago, IL, US
Upcoming Shows: 41
e.t.c. Theater at Second City - Chicago
location 60614, 230 W. North Ave, Chicago, IL, US
Upcoming Shows: 56
Fisher Theatre - MI
location 48202, 3011w Grand Blvd #f100, Detroit, MI, US
Upcoming Shows: 116
Genesee Theatre
location 60085, 203 N. Genesee St, Waukegan, IL, US
Upcoming Shows: 16
Hard Rock Live Northern Indiana
location 46406, 5400 West 29th Avenue, Gary, IN, US
Upcoming Shows: 24
Hobart Art Theater
location 46342, 230 Main St., Hobart, IN, US
Upcoming Shows: 7
House Of Blues - Chicago
location 60654, 329 N Dearborn St, Chicago, IL, US
Upcoming Shows: 40
Judy's Beat Lounge at Second City - Chicago
location 60614, 230 W. North Ave, Chicago, IL, US
Upcoming Shows: 40
Show More