The Cosmic Underground Show-Valentine’s Day Matinee
Feb14
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 Ave
Musical will have U.S. premiere at The Athenaeum Center for Thought & Culture
Feb14
Theatre & 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, Avenue
The Glenlivet 55 Legacy Experience, by Park Hyatt Chicago
Feb14
Festivals, 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 Ave
Valentine’s Day at NoMI Kitchen
Feb14
Festivals, 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 Ave
Imagining Tomorrow
Feb14
Museums, 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…

Saturday, February 14th
5:00 p.m.9:00 p.m.
Forum 301 Chicago
301 W Ohio
Josh Johnson Live!
Feb14
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. State
ComedySportz Chicago
Feb14
Music & 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 St
Museum After Hours: Chemistry in Nature
Feb14
Museums, 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,
Disney On Ice: Jump In!
Feb14
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…

Saturday, February 14th
6:30 p.m.8:30 p.m.
United Center
1901 W Madison St,
The Infinite Wrench
Feb14
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.
Leaning In
Feb14
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 St
Calvin Evans at The Comedy Bar
Feb14
Music & 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 60611
Valen-Wine’s Day: A Comedy & Wine Pairing
Feb14
Music & 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.
Valentines Day Date Night Cocktail Experience
Feb14
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 Ave
Hamnet
Feb14
Theatre & 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 Avenue
Teatro Zinzanni
Feb14
Music & 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 St
Valentine’s Day Dinner Cruises
Feb14
Tours & 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 Dr
Heartbeat House Party at Shedd Aquarium
Feb14
Museums, 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.
Baby Wants Candy! The Original Completely Improvised Musical
Feb14
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.
Clued In
Feb14
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 Floor
Improvised Jane Austen
Feb14
Music & 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.…

Saturday, February 14th
7:30 p.m.8:30 p.m.
iO Chicago
1501 N Kingsbury St,
Before and After, an instant drama
Feb14
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 Ave
The Improvised Shakespeare Company®
Feb14
Theatre & 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…

Saturday, February 14th
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
The Angels of Lemnos
Feb14
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…

Saturday, February 14th
7:30 p.m.9:00 p.m.
Bramble Arts Loft