Displaying items by tag: Comedy Chicago

Is there anything more alluring than a summer night in Chicago? The lakefront beaches, the meandering pathways, the festivals and street foods, the hidden gardens where free art productions are staged, whatever you like, you can find it in the city during summer evenings. There is no shortage of parks to explore or cultural events to experience, thanks in part to the Mayor’s Night Out in the Parks program that partners with organizations to stage free artistic experiences in neighborhood parks all around the city. One such organization kicked off its summer series with a spectacular – and free – performance of Shakespeare’s As You Like It, now playing throughout Chicago parks through August 2^nd.

Shakespeare’s As You Like It is a comedy that follows Rosalind and Orlando, two lovers who each run away from their own political and familial problems and escape into the Forest of Arden. Disguised as a shepherd boy, Rosalind finds Orlando and convinces him to woo her under the guise of curing him of his love for Rosalind. Multiple couplings occur, lessons of life and love are expounded on, and, as every Shakespeare comedy does, As You Like It ends with a wedding – four to be precise.

foreground - Thomas Russell and Connor O. Locklin. Photo by Steven Townsend, Distant Era.

As You Like It is the 2026 production of Midsommer Flight, a theatre troupe that stages high-quality, accessible performances of Shakespeare’s plays in Chicago. Directed by Producing Artistic Director Beth Wolf, this summer’s production continues to delight audiences and draw crowds, presenting free performances to Chicago communities that aim to bring people together. Midsommer Flight is an Arts Partner with Chicago Park District and a participant in the Mayor’s Night Out in the Parks initiative. They will be performing the classic Shakespeare comedy throughout the summer at different neighborhoods throughout the city, but if you think you’ve seen a Shakespeare production, (seen one, seen them all, right?) I beseech you to venture to one of the parks. At the best of times, Shakespearean stories can be difficult to follow: analogous phrasing, double entendres, prosaic old-timey insults, and slurs; it’s not always easy to follow. Midsommer Flight, however, gives the old texts modernity, witty asides, and an expressive atmosphere that makes the play easy to follow and understand. The acting is superior, and the inclusivity is a delightful and refreshing display of humanity at its finest. Talent of the Midsommer Flight cast would rival that of any Shakespearean theatre company, charging hundreds of dollars for seats, and staging productions in grand halls. And the best part? The productions are completely free to the public. The accessibility, the garden park scenery, and the flowy costuming truly provide a magical experience, embodying the spirit, humanity, and beauty of the arts.

There are many benefits to living in and around the Chicagoland area, but summertime really brings out the best and brightest Chicago has to offer. Night Out in the Parks is but one of the many incredible accessible programs bringing cultural events to neighborhoods to “amplify the artistic and cultural vibrancy of our city in every neighborhood and enhance quality of life across Chicago.” Find out more about Night Out in the Parks here. When initiatives such as this meet the grassroots talent and love shown by Midsommer Flight, magic happens. Whether you like it because it’s in your local park or you like it because it is free, there is truly something for everyone this summer in Chicago. You can truly have it just as you like it. As You Like It will be performed outdoors at six Chicago parks through August 2^nd. Learn more about Midsommer Flight and its mission, and check out the list of upcoming performances at parks throughout Chicago and reserve your free space today!

The Second City e.t.c. is proud to announce its next hit show Improv Supernova, a fully improvised explosion of comedy starting January 22. While Second City is legendary for both razor-sharp sketch comedy and world-class improv, Improv Supernova is all about the latter: no pre-written material, no scripts, and no safety net. Fueled by audience suggestions and inspired by the world we're living in, this show is created live by seasoned Second City artists. Every performance is entirely in the moment and never repeated - pure, high-wire improv from first laugh to final curtain call.

Directed by legendary Chicago comedy thought leader Anne Libera, Improv Supernova's electric cast features Kennedy Baldwin, Anna Bortnick, Chas Lilly, Annie Sullivan, Max Thomas, and Riley Woollen. Musical direction by John Love and stage managed by Abby Beggs.

"Chicago has always been the heart of innovative improvisation," notes director Anne Libera. "The Second City e.t.c.'s Improv Supernova takes that legacy to a new level, featuring some of the best the city has to offer, creating a different performance every night - with improvisation that's deeply human, wildly funny, and built to surprise."

Improv Supernova represents an exciting pivot for the e.t.c. stage. This production redefines the e.t.c. as the professional home for hilarious, story-driven improvisation. Unscripted, unpredictable, and unhinged. The Second City Mainstage has always been known for top-shelf satirical sketch comedy, and now The Second City e.t.c. is home to the best improv show in Chicago. No two performances are the same, and nothing is ever repeated.

Performances start January 22, 2026, and run Thursdays at 8 p.m., Fridays and Saturdays at 7 p.m. and 10 p.m., and Sundays at 7 p.m. In honor of The Second City's founding year, Thursday tickets are $19.59.

Located at 230 W. North Avenue Chicago, IL 60610. Tickets are available at The Second City Box office, by phone at 312-337-3992 or online at www.secondcity.com. 

The producing team includes Ed Wells (CEO), Elizabeth Howard (Executive Producer), Jen Ellison (VP, Creative), Jeremy Smith (General Manager), Thomas J. Troup II (Producer, Resident Stages), and Nick Solideo (Senior Producer).

About the Artists
Kennedy Baldwin (Ensemble)(She/They) is a performer born and raised in Chicago, IL. They started taking improv classes in 2016 at The Second City, CIC, iO and The Chicago Improv Den. They toured with The Second City Touring Company for 2.5 years where they had some of the best times of their life. In 2018, they became a founding member of Logan Square Improv where they produce shows and perform with their best friends.

Abby Beggs (Stage Manager & Lighting Designer) (She/Her) is happy to be back working with the Second City again! Originally hailing from Boston, she moved to Chicago in 2015 to pursue design, production management, and stage management. Her past credits include: Legendary Laughs, She the People, Deck the Hallmark. Gaslight District (The Second City); Bagatelle, Cunning Little Vixen, L'Enfant et les Sortileges, L'incoronazione diPoppea (Roosevelt University); Blue Window (Brown Box Theatre Project); Gallo (Guerilla Opera), Boeing Boeing, Barefoot in the Park, Good People, The Scene (Dorset Theatre Festival), and Fen (Whistler in the Dark,) among others.

Anna Bortnick (Ensemble) (She/Her) is so excited to join The Second City ETC ensemble! She has performed across the country with The Second City National Touring Company. Anna is also a member of the musical improv company, BABY WANTS CANDY and SHAMILTON (Edinburgh Festival Fringe, The Second City.) She received her B.F.A. from Boston University and has trained at the Eugene O'Neill National Theater Institute. She is represented by Grossman & Jack Talent.

Anne Libera (Director) (She, her) is Director of Comedy Studies at The Second City where she also serves as Artistic Consultant. She is an Associate Professor at Columbia College Chicago where she created and coordinates the Comedy Writing and Performance BA. She served as the Executive Artistic Director of The Second City Training Centers from 2001 to 2009. Directing credits include Stephen Colbert's one man show Describing a Circle, Arrivals and Departures, The Madness of Curious George, Computer Chips and Salsa, The Second City Goes to War as well as Second City multiple Second City touring productions all over the world. Her recent book Funnier: A New Theory for the Practice of Comedy is published by Northwestern University Press who also published her first book The Second City Almanac of Improvisation. She served as Director of Improv Pedagogy for the Second Science Project (Second City and UC Chicago CDR) which married the studies of improvisation and behavioral science and co-created the Improvisation for Caregivers program with Caring Across Generations. The long list of her former students who have gone on to success in improvisation and comedy includes (just to name a few): Ashley Nicole Black, Aidy Bryant, Kay Cannon, Chelsea Devantez, Jordan Klepper, Amy Poehler, Kristen Schaal, Asha Ward and Steven Yeun. Anne has presented on topics in improvisation and comedy at the Aspen Ideas Festival, Chicago Ideas Week, Twitter, Code Conference, and guest lectured at the Stanford Business School.

Chas Lilly (Ensemble) (He/Him) is originally from the Commonwealth of Kentucky, but has been living and performing in Chicago for over a decade. When not on the e.t.c. stage, you'll find him playing music with his band (@KidCopter) or improvising with his friends at Logan Square Improv.

John Love (Musical Director, Original Music & Sound Design) (He/Him) plays music. An alumnus of The Second City's National Touring Company, he has played pianos (mostly good, some bad) all across the country and Chicago. He pursues original musical endeavors available on Spotify/social media- working as a studio musician for Ersatz Records and a bandmate for the groups Kid Copter and Vienna.

Annie Sullivan (Ensemble) (she/they) is a writer, performer, and all-around sweetheart originally from Kansas City and an alum of Columbia College Chicago. She's absolutely stoked to be performing with The Second City's E.T.C. cast. Annie is also a former ensemble member of The Second City's National Touring Company (GreenCo forever!). Other comedy credits include Blast! (iO Theatre), Devil's Daughter (iO Theatre), HOLY F*CK (The Annoyance Theatre), and Hot Reads (Logan Square Improv). Annie is currently represented by BMGTalent.

Max Thomas (Ensemble) (He, Him) has been featured on Comedy Central,The Comedy Store West Hollywood, The NBC Break Out Comedy Festival at The Second City Chicago & Hollywood, Zanies Chicago & Rosemont, Tiny Cupboard Brooklyn, Laugh Factory Chicago, Steppenwolf Theater:1919, Black & Funny Festival, Chicago Shakespeare Theater: Othello, Berkeley Rep: Comedian Rhapsody, Woolly Mammoth Theatre: Dance Like There's Black People Watching, Kenan Thompson: The Ultimate Comedy Experience and Lollapalooza Music Festival. He is The Chicago Reader Best Stage Actor 2022.

Riley Woollen (Ensemble) (he/him) is thrilled to be joining The Second City ETC!  He is a comedian and playwright from Brooklyn, New York. Beyond Second City, he's also a founding producer and ensemble member of "The Orbit," Chicago's only improvised show in the round.

About The Second City

The Second City opened its doors in 1959 as a small comedy cabaret and has since grown to become the world's most influential name in improvisation and comedy, celebrating its 65th year in business. The Second City's stages, Touring Companies, and Training Centers across North America have proudly been the launch pad and artistic home for many of the funniest performers, writers, directors, and comedic minds on the planet. As well, for decades The Second City's corporate education and entertainment arm, Second City Works, has supported global businesses using the same methods pioneered on its stages to drive individual growth and organizational improvement.

For more information on The Second City, visit www.secondcity.com and follow The Second City on YouTube, TikTok, Instagram, and Facebook