Chicago Shows - The Second City

Ever heard of this show “Hamilton”?

Shamilton is just like that, but (ahem) better! Expect the same level of hip hop, incredible songs, moving storytelling, stunning choreography and powerhouse singing… except made up on the spot.

The New York Times called Shamilton “One of the top 5 comedy shows to catch”.

Comedy supergroup Baby Wants Candy presents “Shamilton!”, the Hamilton-inspired hip hop improvised musical created in 2016 in LA and playing to sold out crowds all over the place, including the Kennedy Center in DC, a national touring company and weekly sold out shows in New York and LA.

Join the Shamilton cast as they improvise an epic musical based on a historical figure or celebrity of your choosing…including Genghis Khan, Kim Kardashian, Mr. Rogers, or even basketball playing superdog Air Bud. You decide!

It’s the show Lin-Manuel Miranda calls, “cease and desist!”

Baby Wants Candy is a completely improvised, full band musical! Having performed over 3,000 improvised musicals to thousands of fans from Chicago to New York to Singapore to Scotland, this group not only performs in Chicago, New York, and LA but also tours internationally, including multiple sold-out runs at the Edinburgh Fringe Festival!

BWC cast & alumni include Aidy Bryant (Saturday Night Live), Jack McBrayer (30 Rock), Peter Gwinn (Colbert Report), Thomas Middleditch (HBO’s Silicon Valley), Lauren Conlan Adams (Kimmy Schmidt), Jessica McKenna (Party Over Here), Nicole Parker (Elephaba in Wickedon Broadway) and many more. Hailed as “Critic’s Pick” from the New York Times and “Best Improv Ensemble” from the Chicago Magazine, this is one improv show you don’t want to miss!

Cue the laugh track because it’s a very special episode of your favorite long running tv show! The gang gets up to the same ‘ol wacky shenanigans that you remember in this one hour comedy show performed in front of a live audience (that’s you!) but this time it’s completely made up on the spot! Watch all the will-they-won’t-theys, loveably bad bosses, and zany next door neighbors that tv raised you on now with much lower budgets!

Don’t miss Chicago’s rising comedy stars before they hit TV, plus surprise guests from Netflix and Comedy Central! Get your tickets now for an unforgettable night of laughter!

Chill AF Presents the best comedians Chicago has to offer, plus special drop-ins from prominent name comedians you’ve seen on SNL, Comedy Central, and Netflix

After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of crime, secrets, and scandals right before your eyes. The performers will keep track of facts, follow leads, and conclude who is the murderer, all while you take in a comedy experience unlike any you’ve seen before. During the show, they’ll employ the tropes, character archetypes, and influences of Hercule Poirot, Miss Marple, Sherlock Holmes, Nick and Nora Charles, Encyclopedia Brown, and just a dash of Scooby-Doo.

Chicago’s top comedians battle it out for laughs, glory, and sweet sweet points in an interactive game show, featuring a live studio audience (that’s you!) Performers go head to head in a series of hilarious challenges inspired by classic game shows like The Dating Game and The Price is Right, and current hits like Game Changer and Taskmaster. Wheel of Improv will leave your head spinning – with laughter!

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Ten Dollar Comedy is a weekly comedy showcase featuring some of Chicago’s best improv, stand-up, and sketch – all for only $10.

This show is produced and hosted each week by Top Dollar Comedy, a comedy collective that features a rotating cast who have performed all over the world together. The ensemble includes: Carly Olson, Eric Muller, Eric Pedersen, Erin Goldsmith, Jonny Nelson, Peter Corey, and Deanna Ortiz.

A Valentine and Love theme Stand-up comedy show

Unfortunately-titled sketch group ‘Catastrophic Success’ presents, “ALL’S WELL THAT ENDS,” a sketch revue of despicable proportions, directed by Laurel Krabaucher with music by Ryan Miera. Following a sold-out stint at the Den Theatre, Sophia Brazda, Mikey Fried, Jake Jones, and Grant Batdorff bring their surreal, highly theatrical style of sketch to the Second City stage, bringing to light dark comedy through music, monologue, and a dash of self-hatred. If you’ve seen too many sketch shows, we’ve got good news for you: this one ends.

An “educomedy” about local advocacy groups and how you can get involved! A mix of “Last Week Tonight,” “Drunk History,” sketch, and improv that explains the issues in an entertaining way. Featuring local groups you can connect with to make a difference! Learn, laugh, and get involved. Proceeds go to the featured cause.

Ballet Flats for Dinner is an autobiographical solo comedy show written and performed by Bridget McGuire. A mix of stand-up and storytelling, Ballet Flats tells the story of McGuire’s life growing up with intrusive thoughts, a form of OCD. From thinking she was pregnant at age 11, to wondering if she killed her friend’s boyfriend at 25, to finally getting help at the ripe old age of 38, Ballet Flats will hopefully have you laughing the entire time.

This show is a fun and entertaining time meshing together Groundhogs Day, Valentine’s Day and a whole lot of chaos and improv! Perfect for everyone wanting to have a good laugh!

Get your gals pals, your pal gals, and your gals ready as Kellie and Kitty take the stage for this Galentines-themed event. This goes beyond just the gals; it is for anyone who has ever been in a relationship or breathed. As you laugh the night away, get ready to dive into romance, hot gos, and whatever else your mind can imagine.

Does your love life have you asking, “Am I… The Problem?”

Then don’t miss the musical comedy for the unlucky in love!

Meet Gigi, a twenty-something hopeless romantic with a knack for attracting the wrong guy. With relatable humor, catchy tunes, and a hilarious cast, “Am I The Problem?” is the laugh-out-loud show perfect for anyone who’s ever questioned their dating choices.

The Chicago premiere stars Alex Irwin, Chris Ward, Eli Chamberlin, and Grace Lenaghan; along with acclaimed Music Director Alex Rembold.

Catch the latest work from producer Grace Lenaghan at the Blackout Cabaret this February, and follow along @amitheproblemmusical.

Yes AHHH is back with a winter weather show ready to delight and fright. Inspired by Steven King novels, the sun going down at 3:00 pm, and New Year’s resolutions you already broke, the Yes Ahhh group of improvisers will take your suggestions to new heights as you buckle in for a scary evening. Bring some hot cocoa and a warm blanket or risk these bone-chilling stories to creep right into your soul.

FLEECED is an improvised puppet show for adults. Each week the puppets of Fleeced use the old school charm of children’s puppet TV to teach the audience a series of new lessons inspired by the letter and word of the day.

Only Killers in the Building – A Night of Unforgettable Comedy
From the Producers of Chicago’s Funniest

Get Ready for the Ultimate Stand-Up Comedy Experience!
Only Killers in the Building features top-tier comedians from HBO, Netflix, Hulu, Peacock, and more. Handpicked for their headline status, these performers bring their A-game for a night of world-class comedy you won’t forget.

What to Expect:

• Top Talent: Comedians from Netflix, Hulu, HBO, and beyond, live and ready to bring their best material to the stage.
• A Show to Remember: Enjoy nonstop laughs and unforgettable moments, whether you’re a Chicago local or visiting for the night.
• The After-Party: The fun doesn’t stop after the show! Join us for an exclusive after-party at Sluggers World Class Sports Bar—just steps away from the theater! All activities are free for attendees.

Exclusive After-Party at Sluggers:
After the comedy show, join us for a FREE after-party at Sluggers, the ultimate sports bar in Chicago, directly across from the field! Here’s a taste of the incredible experience waiting for you:

• Free Batting Cages: Step into the world-famous batting cages for a fun and free activity—whether you’re a pro or just having fun, it’s the perfect way to let loose after a great show!
• Free Arcade Games: Play classic arcade games like skeeball, air hockey, pinball, and electronic basketball. All games are free for attendees to enjoy throughout the night.
• Dueling Pianos & Sing-Along: Sing, clap, and dance along to the hottest tunes in the interactive Dueling Piano Bar! Talented musicians will play a wide variety of genres from rock to top 40 hits—free for all partygoers!
• Food & Drinks: Enjoy delicious snacks and drinks including wings, burgers, pizza, and more, as part of your after-party experience.
• Vibrant Neighborhood Vibes: Sluggers is all about inclusivity, fun, and meeting new people! The lively atmosphere is perfect for mingling with fellow comedy lovers and creating lasting memories.

Don’t Miss It!
This exclusive after-party is the perfect way to cap off your night of comedy. With food, drinks, games, and entertainment, there’s no better place to unwind and keep the celebration going.

Get your tickets now for Only Killers in the Building, and don’t miss out on the fun! You’ll have a night to remember with the best comedy and the best after-party in Chicago!

Get Tickets Today!

Millennials take on Generation X in a battle to see which generation is funnier. The audience votes at the end of the show. Featuring some of the best comics in Chicago, Hosted by Todd Glover

Get Ready for the Ultimate Stand-Up Comedy Experience!

From the creators of Only Killers in the Building, experience an unforgettable night of world-class comedy at Chicago’s most iconic comedy venue. Proudly sponsored by Orso’s Italian Restaurant, Greenstar Brewery, Sluggers World Class Sports Bar & Grill, Dueling Pianos, and Inner G Restorative & Holistic Care, this is more than just a show—it’s an epic night filled with laughter, delicious food, refreshing drinks, and great music.

Chicago’s Funniest: More Than Just a Show—It’s an Experience!

Get Ready for an Unforgettable Night Out in the Heart of Chicago!

Imagine this: A night of non-stop laughter, unforgettable memories, and the perfect place to unwind with great food, drinks, and even better company. Chicago’s Funniest isn’t just another comedy show—it’s an experience you’ll look forward to again and again!

What to Expect: The Perfect Night Out

A Lineup You Won’t Find Anywhere Else: Featuring top talent from Netflix, Hulu, HBO, Amazon Prime, Peacock, Showtime, and the best comedy clubs around the country, this show includes top-tier comedians you’ve seen and loved on your favorite streaming platforms. Handpicked for their headline status, these performers bring their A-game for a night of world-class comedy you won’t forget.

A Show to Remember: Whether you’re a Chicago local or visiting for the night, this is your go-to spot for a great time. Enjoy world-class comedy in a vibrant, fun environment that’ll leave you with a smile long after the show ends.

The After-Party: The fun doesn’t stop when the show ends! Join us for an exclusive after-party at Sluggers. After the comedy show, head over to Sluggers, the ultimate sports bar in Chicago, located right by Wrigley Field. Here’s a taste of the incredible experience waiting for you:

• Free Batting Cages: Step into the world-famous batting cages for a fun, free activity—whether you’re a pro or just having fun, it’s the perfect way to let loose after a great show!
• Free Arcade Games: Play classic arcade games like skeeball, air hockey, pinball, and electronic basketball. All games are free for attendees to enjoy throughout the night.
• Dueling Pianos & Sing-Along: Sing, clap, and dance along to the hottest tunes in the interactive Dueling Piano Bar! Talented musicians will play a wide variety of genres from rock to top 40 hits—free for all partygoers!
• Food & Drinks: Enjoy delicious snacks and drinks, including wings, burgers, pizza, and more, as part of your after-party experience.
• Vibrant Neighborhood Vibes: Sluggers is all about inclusivity, fun, and meeting new people! The lively atmosphere is perfect for mingling with fellow comedy lovers and creating lasting memories. It’s the perfect spot to unwind with delicious food and drinks, mingle with the comedians, and enjoy the vibrant energy of Chicago’s comedy scene. This after-party is where memories are made—a relaxed, fun, and lively place to soak up the energy of the night!

Incredible Prizes: Our sponsors have outdone themselves with fantastic giveaways, including:

• $500 Greenstar Brewery VIP Tasting Tour for 12: Enjoy a tour led by Brewmaster Brandon Stern, a pint of award-winning Amber Lager, and a tasting of four organic craft beers.
• $500 Sluggers Gift Card: Enjoy food and drinks at the world-famous Sluggers Sports Bar & Grill near Wrigley Field, with arcade games, batting cages, skee-ball, and more.
• $500 Cash Prize: T ake home some extra joy to top off your evening!
• $500 Gift Certificate from Inner G Restorative & Holistic Care: Pamper yourself with a wide range of therapeutic services including full-body hot stone massages, Manual Lymphatic Drainage, Medical Massage, Prenatal Massage, and more. Relaxation and wellness await you!

Why You Shouldn’t Miss It

A Night You’ll Look Forward To: Whether you’re coming for the comedy, the after-party, or the chance to win one of our amazing prizes, Chicago’s Funniest is the perfect place to create memories with friends, meet new people, and have an unforgettable time in the heart of the city.

How to Join the Fun

Buy your tickets today for a chance to win one of our amazing prizes and experience a night of laughter and excitement you won’t forget!

The Perfect Night Out is Waiting for You!

Get your tickets now and don’t miss out on the fun! You’ll have a night to remember with the best comedy and the best after-party in Chicago! Hurry and grab your tickets before they sell out!

Go All-In on longform improv with host team Lavalier. Six teams play for a chance to win completely worthless prizes awarded by our esteemed panel of improv judges, followed by a performance by the judges themselves. Seven teams, six weeks, two hours of hilarious improv comedy. Nothing has been scripted or prepared in advance. It will all be made up before your very eyes!