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Music & Comedy, Theatre & Performing Arts
The Cosmic Underground Show-Valentine’s Day Matinee
The Cosmic Underground Show blasts off for a 90-minute immersive comedy, magic, and mind-reading show. Cosmic founders and real-life couple Harrison Lampert (a quirky sleight-of-hand…
Saturday, February 14th
4:30 p.m. – 6:00 p.m.cosmic underground theater
3433 W Fullerton AveTheatre & Performing Arts
Musical will have U.S. premiere at The Athenaeum Center for Thought & Culture
After a highly successful run in Europe, the U.S. anticipated premiere of Bernadette, The Musical has been set!The inspiring musical about the courageous story of…
Saturday, February 14th
5:00 p.m. – 7:00 p.m.Anthenaeum Theater
2936 N. Southport, AvenueFestivals, Fairs & Special Events
The Glenlivet 55 Legacy Experience, by Park Hyatt Chicago
Park Hyatt Chicago presents a singular offering centered on The Glenlivet 55 Year Old – Edition No. 1 of The Eternal Collection. Matured for more…
Saturday, February 14th
5:00 p.m. – 7:00 p.m.Park Hyatt Chicago
800 N. Michigan AveFestivals, Fairs & Special Events
Valentine’s Day at NoMI Kitchen
VALENTINE’S DAY DINNER AT NoMI KITCHEN Saturday, February 14th from 5:00pm – 9:00pm View Menu A night to savor for you and yours, indulge in…
Saturday, February 14th
5:00 p.m. – 9:00 p.m.NoMI
800 N. Michigan AveMuseums, Galleries & Exhibitions
Imagining Tomorrow
The exhibition asks fundamental questions about the future of art, culture, and community, positioning Forum 301 as a space not only for presentation but for…
Music & Comedy
Josh Johnson Live!
Comedian Josh Johnson will perform live at The Chicago Theatre on Feb. 14-15, 2026.
Saturday, February 14th
5:00 p.m. – 10:00 p.m.The Chicago Theatre
175 N. StateMusic & Comedy, Theatre & Performing Arts
ComedySportz Chicago
Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…
Saturday, February 14th
6:00 p.m. – 7:30 p.m.Malarkey Comedy Company
1501 N Kingsbury StMuseums, Galleries & Exhibitions
Museum After Hours: Chemistry in Nature
Explore the wild side of romance at Chemistry in Nature, an adults-only night celebrating the strange and spectacular world of animal mating behaviors. Wander the museum…
Saturday, February 14th
6:00 p.m. – 9:00 p.m.The Field Museum
1400 S Lake Shore Dr,Theatre & Performing Arts
Disney On Ice: Jump In!
Get ready for a magical adventure as Disney On Ice unveils its newest show, Jump In!, at United Center from February 12-15, 2026! The adventure begins…
Music & Comedy, Theatre & Performing Arts
The Infinite Wrench
Don’t miss the longest running late-night show in Chicago! At The Infinite Wrench you’ll see 30 original plays in 60 minutes written and performed by…
Saturday, February 14th
7:00 p.m. – 8:00 p.m.The Neo-Futurist Theater
5153 N. Ashland Ave.Theatre & Performing Arts
Leaning In
Leaning In is a playful, tender, and deeply human look at love in all its forms—the kind that makes you laugh, choose each other again,…
Saturday, February 14th
7:00 p.m. – 8:00 p.m.Park Church
1001 N Crosby StMusic & Comedy
Calvin Evans at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Chicago native Calvin Evans’ comedy career…
Saturday, February 14th
7:00 p.m. – 8:30 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611Music & Comedy
Valen-Wine’s Day: A Comedy & Wine Pairing
This Valentine’s Day, fall in love one glass at a time. Valen-Wine’s Day pairs six of Chicago’s best stand-up comedians with six different wines, creating…
Saturday, February 14th
7:00 p.m. – 8:30 p.m.iO Theater
1501 N. Kingsbury St.Festivals, Fairs & Special Events
Valentines Day Date Night Cocktail Experience
Shake Up Your Valentine’s Day Weekend! Celebrate love, friendship, or just a good time with our special Valentine’s Cocktail Class at Industry Ales! Whether you’re…
Saturday, February 14th
7:00 p.m. – 9:00 p.m.Industry Ales
230 S Wabash AveTheatre & Performing Arts
Hamnet
“Elegant and beguiling” – Evening Standard (UK) Warwickshire, 1582. Agnes Hathaway, a natural healer, meets the Latin tutor, William Shakespeare. Drawn together by powerful but…
Saturday, February 14th
7:00 p.m. – 9:30 p.m.The Yard at Chicago Shakespeare
800 East Grand AvenueMusic & Comedy, Theatre & Performing Arts
Teatro Zinzanni
Tickets are on sale now at https://zinzanni.com/chicago/tickets/ “Best Night Out” – CS Magazine | “You must see to believe!” – Forbes Teatro ZinZanni, Chicago’s most…
Saturday, February 14th
7:00 p.m. – 10:00 p.m.Teatro ZinZanni – Cambria Hotel
32 W Randolph StTours & Attractions
Valentine’s Day Dinner Cruises
Set sail with your special someone on an unforgettable experience with a Valentine’s Day Dinner Cruise. Celebrate with your Valentine or Galentine, dining and dancing…
Saturday, February 14th
7:00 p.m. – 10:00 p.m.City Cruises – River Esplanade
455 N Cityfront Plaza DrMuseums, Galleries & Exhibitions, Music & Comedy
Heartbeat House Party at Shedd Aquarium
Feel the love and the rhythm at the first-ever Heartbeat House Party! Celebrate Valentine’s Day beneath the waves with house music and aquatic allure. Dress…
Saturday, February 14th
7:00 p.m. – 11:00 p.m.Shedd Aquarium
1200 S. Lake Shore Dr.Music & Comedy, Theatre & Performing Arts
Baby Wants Candy! The Original Completely Improvised Musical
“CRITICS’ PICK. TRULY AMAZING!” – New York Times “BEST VISITING IMPROV COMEDY!”– TimeOut NY “HIGHLY RECOMMENDED!” – The Onion “★★★★★” THEY ARE AN ENTERTAINMENT PHENOMENON AND I…
Saturday, February 14th
7:30 p.m. – 8:30 p.m.The Second City
1616 N. Wells St.Music & Comedy, Theatre & Performing Arts
Clued In
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…
Saturday, February 14th
7:30 p.m. – 8:30 p.m.The Second City
1616 N. Wells St., Theater on the Second FloorMusic & Comedy, Theatre & Performing Arts
Improvised Jane Austen
Celebrate Jane Austen’s birthday all winter long with Improvised Jane Austen! Just one day cannot encapsulate a proper observation of Jane Austen’s life and work.…
Theatre & Performing Arts
Before and After, an instant drama
Life is defined in moments. Before and After explores the story leading to a life-changing event and the impact of that instant on all that…
Saturday, February 14th
7:30 p.m. – 8:30 p.m.Studio Momentum
1541 W Belmont AveTheatre & Performing Arts
The Improvised Shakespeare Company®
The Improvised Shakespeare Company® proudly presents its critically-acclaimed, long-running hit show Improvised Shakespeare Chicago, now in its 19th year! Join us for an evening of…
Theatre & Performing Arts
The Angels of Lemnos
Clark Week Productions is proud to present The Angels of Lemnos by Jim Henry for a very special 30th anniversary run with a portion of…

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