Displaying items by tag: Comedy Chicago

Tis' the season for laughter and cheer! The Second City is decking its holiday lineup with shows for every sense of humor; including two hilarious holiday shows that promise big laughter for all ages. Whether you're craving a nostalgic night out or starting a new holiday tradition, The Second City makes any winter outing merry and oh, so bright.

Make hilarious holiday memories with The Second City. Save 25% on tickets to Not Today, Santa and Pandemonium, Please Hold in December if booked between September 17 and October 9. Use code HOLIDAY2026 at checkout.

For showtimes and tickets please visit secondcity.com or call our box office at (312) 337-3992. The Second City is located at 1616 N. Wells Street.

The Second City's Holiday Lineup
Not Today, Santa
November 25 – December 28, 2026
Tickets start at $45.

Not Today, Santa is The Second City's ultimate holiday comedy celebration, featuring a merry mix of fan-favorite sketches, sharp satire, and festive fun. Packed with laughs for anyone who has survived a family holiday gathering, this seasonal revue is the perfect holiday outing for friends, families, and office parties alike.

Rudolph Runs Wild
November 27 – December 27, 2026
Tickets are $30.

Share silliness this holiday season with Rudolph Runs Wild, a jolly extravaganza for kids, parents, grandparents, aunts, uncles, and reindeer of all ages! Featuring a fun and festive blend of family-friendly songs and sketches from The Second City's rich comedy archives, fresh new material written specifically for young audiences, and – of course – the ridiculous improv hijinks The Second City is world famous for. Brighten your winter with this one-of-a-kind interactive theatrical experience offering audience members, young and old, the chance to enjoy the comedy fun both from their seats and by joining The Second City performers onstage!

Also Playing at The Second City
Searching for mistletoe free options? We get it! Beat the Scrooge accusations by seeing Second City's hit revues Pandemonium, Please Hold and Reality Detox: The Improv Experience. It's the perfect date night plan without the holiday overload. Turn bah humbug into a night full of laughter with these hit shows.

Pandemonium, Please Hold
Open Run
Tickets start at $40.

The Second City's 114th Mainstage Revue Pandemonium, Please Hold is a loud, fast, and gloriously unhinged night of comedic mayhem. The Second City's six-person cast cranks the amps and stage dives headfirst into the chaos with blistering sketch comedy, unpredictable improv, explosive live music, and absolutely zero chill. Cathartic and wildly funny, brace for pandemonium and join us for a night of full-volume hilarity. Come scream into the abyss with us.

Reality Detox: The Improv Experience
Open Run
Tickets start at $40

Reality Detox: The Improv Experience is a high-energy night of improvisation from The Second City, with a few sketch surprises mixed in along the way. Built fresh each night and shaped by the people in the room, every performance is different from the last. Funny, fast, and wildly unpredictable, it's a chance to escape reality and enjoy a night of laughter. Come be part of the comedy magic.

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 improv and comedy. Second City's stages, Touring Companies, and Training Centers across North America have proudly been the launch pad for many of the funniest names on the planet, including John Belushi, John Candy, Steve Carell, Stephen Colbert, Chris Farley, Tina Fey, Keegan-Michael Key, Eugene Levy, Tim Meadows, Bill Murray, Mike Myers, Suzy Nakamura, Catherine O'Hara, Amy Poehler, Gilda Radner, Sam Richardson, Joan Rivers, Amber Ruffin, Robin Thede and Steven Yeun, among many more.

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!