Despite New York or Los Angeles often being the final destination for comedians, Chicago remains the most important.
Performers, from every corner of the world, stop by to hone their craft at the nation’s best stages. Theaters like Second City and The Annoyance have been a springboard for launching the career of many legends. Equally, clubs like the renowned Laugh Factory and Zanies have been graced by the greatest stand-up comics of all time.
The best thing about comedy is that it is always evolving; there are constantly legends-in-the-making. Once new talent touches down in Chicago, they find an endless space to practice.
Over the years, the city has seen brilliant expansions of old concepts. Many comedians have created their own productions that are no longer limited to just stand-up or improv.
As more shows pop up, innovative minds seek to give audiences a truly unique experience. If you find yourself in Illinois for any reason, these are the top 10 best comedy shows to check out in Chicago- in no particular order.
Top 10 Best Comedy Shows in Chicago
My Best Friend is Black
at The Lincoln Lodge Theater w/pop ups
Every fourth Thursday at 8pm
Cast Member Mike Atcherson performs a sketch during a show. | Photo Credit: Katia Jackson
In a time where black voices are needed more than ever, My Best Friend is Black is the loudest, and proudest, in Chicago. Brought to life by a passionate and brilliant all-black cast: Mike Atcherson, Justin Walker, Chloe Mikala, Arlieta Hall, Daryn Robinson, Rho Hudson, and Marcus Banks. The daring variety show is not only a necessity, but also a must-see revolution.
Chicago has been a consistent home for black sketch groups; years ago, there was 3Peat, the Martin Luther Kings of Comedy, and BAPS (Beautiful and Powerful Sisters.) While sharing similarities with its predecessors, My Best Friend is Black manages to carve a league all of their own. Their format is classic – each show involves sketch, improv, stand-up, and crowd participation. The dynamic chemistry of the producers is on full display when they take center stage as a cast and breathe life into every medium.
My Best Friend is Black cares deeply about creating a fun, inclusive, and warm space that showcases different parts of black culture. By sharing the space with various mediums of comedy, they paint a poignant and nuanced portrait of what it means to be Black. It’s an innovative, all-encompassing way to give the audience a powerhouse of an experience while providing a necessary platform to Black performers.
Their photographs are captured by Katia Jackson, who was recently featured in Comedy Gazelle for her snaps of the shows.
If you’re ever planning a trip to Chicago, make sure it’s on the fourth Thursday of the month and follow them on Instagram to score tickets. It’s a necessity.
The Humboldt Jungle
at a Secret Location
Every 3rd Wednesday at varying times
The Humboldt Jungle venue | Photo Credit: Nathan Weil
Ever been to a show in a basement? It’s less creepy than it sounds, and it has a high chance to be better than any club you cop a ticket to. The Humboldt Jungle is one of the coolest and most exclusive shows in the city.
In an unassuming house on a block that probably mirrors your own, there have been numerous sold-out events produced by Joe Eames and Nathan Weil. The gorgeously ambient basement show started as a passion project for musicians to have a unique space to perform and stay at if they needed it. It eventually evolved into a comedy show with music shows running every other month.
The best performers in the world walk down a set of creaky steps to the aptly named “Jungle.” The basement is, well, a basement, but the setup is professional; monitors to record every aspect of the show, nearly 100 chairs, beautiful lights adorning the stage, speakers, cameras and, of course, pizza. Tickets drop and sell out the same – quickly. The address is given upon purchase to maintain the exclusivity.
The goal for The Humboldt Jungle has always been to be a unique venue that people can’t find somewhere else and where they can see top quality artists do their thing in an intimate setting. They certainly succeed in creating one of the best comedy shows in Chicago.
While they are on a hiatus until January, you have a chance to follow their website and keep your eyes peeled for the next show.
Tight Ship Comedy
at Half Sour
Every Thursday at 8pm
Tight Ship Comedy’s poster | Sourced from Instagram
The only entrant on this list that is free, Tight Ship Comedy is a secret gem in the city’s South Loop neighborhood.
It is produced by Chicago favorites – and revered comedy veterans – Chris Trani, Jeff Brumfield, Pat Bolduc, & John Gasper. Held in a classy underground speakeasy, Tight Ship is an exclusive and amazing show with top notch talent.
Half Sour is the perfect spot; it’s in a trendy neighborhood, serving incredible food, drinks, and creating an ambiance with retro music. Trani, Brumfield, Bolduc, and Gasper match with providing (and hosting) the best comedians the world has to offer.
Generally, due to the free tickets and undeniably cool venue, the show’s seating is first come first serve. Occasionally, with ten minutes to show time, there is standing room only. This never deters anyone; many audience members proudly cram in to watch true artists at work. The comedy show they get is worth far more than the price of admission. Need I remind you? It’s zero dollars.
It is a must see and a fantastic prelude to the weekend. Keep up with them on Instagram.
LadyLike
at The Lincoln Lodge Theater
Every 3rd Tuesday of the month at 8pm
Sourced from Instagram.
As the great American author Beyonce once asked, “Who runs the world? Girls.”
To say that comedians Lucia Whalen and Gena Gephart felt what Bey was saying would be an understatement. The world of stand-up has always been male-dominated and thanks to that very fact, gender inequality reflects in shows of every size. Many of the city’s biggest shows often feature an all-male lineup and most of the headliners in Chicago are men. In 2016, Gena and three other female comics started Ladylike, a comedy show that showcases women and queer performers from around the globe.
Ladylike has a special caveat; the performers are telling some of their most disgusting, gross, and unladylike stories to a very warm and receptive audience. A nice addition comes when the audience anonymously submits their own stories for the host to read aloud. It creates a bond between the crowd and performers as both share unsavory moments about their lives – all while laughing hysterically together.
The show has also been known for its charity work, such as working with Feeding People Through Plants – an organization that builds tents for people experiencing homelessness. Be sure to support this women-owned, operated, and curated show anytime you’re in the city. Follow @ladylikechicago on Instagram.
Lowkey Funny
at The Laugh Factory
1st Friday of the Month at 9:30pm
Lowkey Funny’s promo poster | Captured by Ashley Lane.
Lowkey Funny is the closest thing to a block party you will find; there’s drinks, good food, a packed house, and some of the greatest stand-up comics alive creating nonstop laughs. It is the place to be on a Friday night.
In its relatively short tenure, Lowkey Funny has quickly blossomed into one of the best shows staged at Laugh Factory. The presentation is unique – the show is exclusively stand-up, while the social media page runs various forms of sketch and promotional comedy utilizing new talent.
The producers — Matthew Bright, Rachel Hall, Ali Drapos, Ontonio Kareem, Dan Cass, Ashley Lane — are extremely active. They make a concerted effort to platform Black, brown, and marginalized voices within the show and online content; they aim to give an amplified voice to those with interesting perspectives to share their unique personal experiences.
The Laugh Factory is world famous, meaning that the most masterful comedians grace the stage. Lowkey Funny frequently gets acts such as: T Murph (Woke, HULU); Felonious Munk (For Life, ABC); Marilee (Southside, Comedy Central).
Lowkey Funny frequently spotlights the very best up and coming comedians alongside the heavy hitting veterans. By doing this, they create unmatchable lineups to give the audience a fresh, hilarious show. The producers that are stand-up comedians — Drapos, Kareem, Hall and Cass — are brilliant and fiercely talented; with a strong arsenal at the helm, a few of them may step into the line up occasionally and add more gas to the blazing spectacle.
Find some of the very best stand-up comedians at Lowkey Funny and follow their page to buy tickets to the one of the most electrifying comedy shows in the city.
Sauteed Stand Up
at The Lincoln Lodge Theater
1st and 3rd Sunday of each month at 7:30pm
Kyle Scalan performs while his partner, Gina Palm, left, cooks | Courtesy of Sauteed Stand Up.
It is no secret that competitive cooking shows are some of the most popular programs out. Whether it is Hell’s Kitchen, Master Chef, or Kitchen Nightmares, they are the most viewed content on any platform. These culinary shows have an unexpected sense of humor to them that is usually rooted in a chef’s incompetence, a simple dish gone wrong, or a panel of mouthy judges. Now, imagine that but replace all of the professional chefs with bumbling stand-up comedians.
There you have one of the most unique – and tasty – shows in the city: Sauteed Stand-Up.
The show was brought to life by producers Tad Walters, Nathan Hall, Josh Smith and Katie Kincaid. The first few editions kicked off in early 2020, just before the COVID-19 shutdowns. After the pandemic, it took a full year to start the show back up.
The format is astounding; a cooking competition comedy show where two teams, equipped with two stand-up comics each, make a dish live on stage for professional chef judges. The comedians must also perform their sets in between the cooking process. They are given a secret ingredient at the beginning of the show that they must incorporate into the dish.
Comedian Tad Walters serves as the host; he is also an accomplished sous chef, a position that aids in landing qualified judges for Sauteed Stand-Up. Those professionals judge the comedians on the strength of their cooking, not their comedy. With food, hilarity, crowd engagement and a new take on a Gordon Ramsey type concept – it’s one of the best live experiences you can get in Chicago.
Check out Sauteed Stand-Up on Instagram and TikTok @sauteedstandup. Head to their website to purchase tickets; the next round of shows will be tournament style competitions that you do not want to miss.
Latin XL
at The Laugh Factory
Second to last Friday of the month at 11:30pm
Latin XL being advertised on the world-famous Laugh Factory’s marquee. | Courtesy of LatinXL
Latin XL is comedy’s version of a nightclub – an unforgettable experience that feels like a never-ending summer night. It is only fitting that the producers are larger than life themselves and legends-in-the-making Ken Flores and Rene Humberto are two unstoppable forces in the Chicago scene.
Kicking off close to midnight at The Laugh Factory on a Friday, Flores and Humberto bring a party vibe to stand-up comedy.
The show was born with a simple mission: to highlight the Latin talent in the city and surrounding areas. The “XL” was introduced to include all kinds of comics, with pride in putting up those who have not yet graced the stage of Laugh Factory. The goal, Flores noted, is to get funny comedians in front of management thus making Latin XL the bridge. The show reaches far beyond management as the social media exposure has skyrocketed; Juanmanuel Vizcarra (@refsproductions) creates breathtaking promo, clips, and videos using his arsenal of talents.
Though Latin XL has staged their final show for the year, they start back up in January. Tickets go quickly so be sure to follow them on Instagram, along with the producers Ken Flores & Rene Humberto.
After Hours
at Zanies Chicago
Every Saturday at 11:15pm
Courtesy of Brian Hicks
On Google, the description for Zanies reads “decades old comedy club that hosts nationally known headliners.”
It is legendary to the city of Chicago and wears its history proudly. As soon as you enter, you see the walls filled with framed portraits. The wall itself is just as historic as the people who grace it; the likes of Moms Mabley, Paul Mooney, Gallagher, Jerry Seinfeld, Eddie Murphy and hundreds of other legends are posted – even better, each photo is signed.
Every young comedian aspires to have their headshot on the wall someday. The more immediate goal is to perform at Zanies and that is no easy task; getting booked is hard. That’s where After Hours comes in.
Brian Hicks, the current General Manager, introduced the new show after the pandemic. It serves as an opportunity for up-and-coming comics to get stage time in the legendary venue.
While most shows in the city rotate hosts on recurring shows, Hicks opted for a permanent one in the form of Calvin Evans. Evans has a long resume: a finalist on NBC’s StandUp, a new face with JFL Montreal, a list of TV credits, and being frequently recognized as one of Chicago’s funniest (and charismatic) stand-up comedians. He sometimes incorporates his trusty piano into the act, creating a nice mood for a Saturday night.
Having a veteran lead a show that gives a lot of comedians their first Zanies’ spot is a genius move. The audiences are warmly receptive, Evans sets the stage, and the comedians bring their absolute best. There’s not many shows out with true heart and stakes.
Supporting new talent, chilling in a historic venue, and laughing until you cry is definitely a great way to cap your Saturday night.
Chicago Comedy Underground
at House of Blues
Every Tuesday at 7:30pm & moving to Thursdays in 2023
Courtesy of Chris Trani
The most elegant entry on this list takes place in the dazzling Foundation Room at the House of Blues. Produced by Chris Trani and Danny Hein, Chicago Comedy Underground showcases national and local headliners every week.
The room itself is stunning, with a sophisticated atmosphere, fancy drinks, classy lounge booths, and top tier food.
The Foundation Room is normally members only, however thanks to the show on Tuesdays, it is open to the public for the comedy showcase. There’s significant appeal to the experience: The service is tip top, the lighting is romantic, the ceiling is carved with gorgeous artwork, and the comedians are just an inch away making the show more engaging.
Chicago Comedy Underground is the perfect date night full of laughs and ambiance.
Follow @chicagocomedyclub on Instagram for show updates and tickets.
The Lodge Flagship Show
at The Lincoln Lodge Theater
Every Friday and Saturday at 8pm
Producer and cast member, Dan Drees performs on the Flagship show. | Photo credit: Shane Anthony
The Lincoln Lodge has a few special things going for it. First, it is the nation’s longest running independent comedy club. Second, it runs more shows on the weekends than any other comedy venue in the state. The theater has three separate performance spaces inside; on any given Saturday, from 7pm until midnight, there are as many as nine different shows that take place. The unique aspect is that a majority of the shows are created by comedians, both new and experienced; The Lodge provides a supportive, free home for their concepts to blossom on any day of the week.
It was hard to narrow this list down as to what the Lincoln Lodge’s best show is. After much consideration, I had to give it to The Flagship show. For two decades, it has been the longest running show at the theater and the most popular.
Producer and cast member Britt Ferguson hosts The Flagship Show. | Photo credit: Shane Anthony
Since 2001, The Flagship Show has increased its talent, popularity, and production. The theater has an ongoing tradition of using a cemented cast of stand-up comedians that take turns hosting the main show.
Much of the expanded success can be credited to the current cast, who also produce the Flagship show: Chris Higgins, Jarrell Scott Barnes, Kyle Scalan, Dan Drees, Britt Ferguson, and Gena Gephart. Though they are often the host, many of them feature on the show alongside the nation’s best comedians and celebrity drop ins (Jeff Ross, Hannibal Buress, David Cross, Bobcat Goldthwait.)
The Lincoln Lodge remains a can’t miss city favorite. It has a spontaneous appeal as people can walk by, gaze inside the huge windows and see the night’s programs listed on a colorful screen. If you ever find yourself in Chicago for a weekend, make sure you breeze by as well.
Follow them on Instagram to plan out your trip to see one of the best comedy shows in Chicago.
