Valentine's day events in Chicago

Check out happening valentine's day events all around Chicago, IL

CHICAGO BOLLYWOOD VALENTINES NIGHTOUT @FAME NIGHTCLUB

 Fri, 13 Feb at 10:00 pm Lore Chicago USD 19 to 180

2026 Chicago Winter Tequila Tasting Festival (February 14) AE

 Sat, 14 Feb at 02:30 pm Kings Dining & Entertainment USD 20 to 89

Tipsy Cupid Sip & Sail Valentine's Day Yacht Cruise (Chicago)

 Sat, 14 Feb at 06:15 pm Burnham Harbor S Dock (Anita Dee 2) USD 39 to 637

Motion City Soundtrack with Say Anything

 Sat, 14 Feb at 01:00 am Riviera Theatre - Chicago

Chaotic Singles VALENTINE'S Party! (Chicago)

 Fri, 13 Feb at 07:00 pm Joy District USD 14 to 20

The Outsiders at Cadillac Palace

 Tue, 10 Feb at 07:00 pm Cadillac Palace

10th Annual: Anti-Valentines Day Valentines Day Crawl

 Sat, 14 Feb at 06:00 pm River North USD 8 to 45

LOVE IS IN THE ATMOSPHERE

 Sat, 07 Feb at 07:00 pm Adler Planetarium USD 55

AirOtic Soirée Presents: LoveStruck (Chicago)

 Thu, 05 Feb Experience 868 USD 48 to 132

Ken-Y Live in Concert! Pre-Valentines Day Weekend

 Fri, 06 Feb at 09:00 pm Stereo Nightclub USD 45 to 108

Metro & smartbar present... An All-Building Event: Valentine's Day Queen!

 Sun, 15 Feb at 10:00 pm Smartbar Chicago

RNB Indoor Rooftop Event Valentine’s Weekend Event (Boo’d Up) Chicago

 Sun, 15 Feb at 03:00 pm VU Rooftop Bar USD 18 to 269

PlayDates Brunch and Day Party

 Sat, 14 Feb at 02:00 pm Punch Bowl Social USD 13 to 69

ROOF on theWit| Sunday Funday: Valentine’s Day Weekend | 2.15.26

 Sun, 15 Feb at 09:00 pm ROOF on theWit USD 34 to 163

3rd Annual All 80's Prom

 Sat, 14 Feb at 08:00 pm Theater on the Lake USD 55

¡Pachanga! Amor Vaquero on Navy Pier

 Sat, 14 Feb at 08:00 pm Bar Sol USD 8 to 35

Chef's Valentines Dinner: Italian Date Night

 Sat, 14 Feb at 06:30 pm Eataly Chicago USD 156

Raks Inferno: A Valentine Speakeasy

 Fri, 13 Feb at 07:00 pm The Newport Theater USD 33 to 43

IRL: Heated Rivalry Singles Mixer!

 Mon, 09 Feb at 06:00 pm Dorothy Free

CUPID'S CRAWL (18+ BARS/CLUBS INCLUDED)

 Sat, 14 Feb at 04:00 pm Good Night John Boy USD 7 to 55

Love In The Making: Valentine's WineMaking Experience & Dinner

 Sat, 14 Feb at 06:00 pm Wild Blossom Meadery and Winery USD 157

Speed Dating Chicago | In-Person | Cityswoon | Ages 29-49

 Sat, 14 Feb at 06:00 pm Bar Moxy USD 43

Valentine's Day at NoMI Kitchen

 Sat, 14 Feb at 05:00 pm 800 N Michigan Ave, Chicago, IL 60611

FiREHAUS: In Heat

 Sat, 14 Feb at 09:00 pm 3352 N Halsted St USD 7 to 23

Lyric Opera of Chicago: Cosi Fan Tutte

 Sat, 31 Jan at 06:00 pm Lyric Opera House - IL

Champagne & Sparkling Wine Fest at Hubbard Inn on Valentine's Day

 Sat, 14 Feb at 05:00 pm Hubbard Inn USD 36 to 47

Valentine's Day 2026 at Alhambra Palace Chicago

 Sat, 14 Feb at 07:00 pm 1240 W Randolph Street USD 103

Love Struck - A Seductive Valentine’s Cabaret in Chicago!

 Thu, 05 Feb at 08:30 pm Experience 868 Events USD 55 to 119

Pamper Your Pup Valentine's Day Event

 Sun, 15 Feb at 11:00 am Bosly's Backyard USD 30

Old Crow's Anti-Valentine's Day Party

 Sat, 14 Feb at 09:00 pm Old Crow Smokehouse USD 5 to 22

Hubbard Inn Uncorked Galentine's Edition

 Fri, 13 Feb at 07:30 pm Hubbard Inn USD 29

Saturday | THE VALENTINE SOCIAL (welcome cocktail included) | The Alston, Members Lounge

Sun, 15 Feb at 12:00 am The Alston

Valentine's Day at Hopsmith

 Sat, 14 Feb at 11:00 am Hopsmith Chicago Free

LOVE SUCKS - A VALENTINE'S DAY EXPERIENCE

 Sat, 14 Feb at 08:00 pm Ambassador Gold Coast - The Chicago Hotel Collection USD 23

TUFF LOVE feat. Rika B, Mayya & Muffy

 Sat, 14 Feb at 04:00 pm 646 N Franklin St, Chicago, IL

The R&B Trolley - Party Tour (Valentines Edition)

 Fri, 13 Feb at 10:00 pm Chalet USD 69 to 85

Meet Your Matchmaker: Four singles. Two blind dates. Live onstage.

 Sat, 14 Feb at 07:00 pm The Lincoln Lodge USD 18

Valentine's Day Dinner & Dancing: Tapas Making & Dance Lessons!

 Sat, 14 Feb at 07:00 pm Get in the Kitchen USD 107

Valentine's Murder Mystery Dinner

 Sat, 14 Feb at 06:00 pm Olive Black Chicago

Galentine's Night @ Era Social Club

 Sat, 14 Feb at 10:00 pm Era Social Club USD 34 to 87

Not Ur Baby

 Sat, 14 Feb at 07:00 pm Replay Lincoln Park

Thursday | The Valentines Match - AI Matchmaking | Hopsmith, Gold Coast

Fri, 13 Feb at 01:00 am Hopsmith Chicago

Valentine’s Days Speed Dating Event

 Sat, 14 Feb at 09:00 pm Chicago's Downtown

SHE LOVES ME / NOT - Dorothy's Valentines Night

 Sat, 14 Feb at 06:00 pm Dorothy Free

Valentine's Day Festa

 Fri, 13 Feb at 06:00 pm Eataly Chicago USD 49 to 240

Valentines Day Hands on: The Art of the Salumi & Formaggi Board

 Sat, 14 Feb at 12:00 pm Eataly Chicago USD 87 to 130

Hands-On: Tiramisù alla Fragole, Valentines Edition

 Sun, 15 Feb at 12:00 pm Eataly Chicago USD 93

Heartthrob Throwbacks at Howl at the Moon Chicago

 Fri, 13 Feb at 07:00 pm Howl at the Moon Chicago Free

Valentine's Painting + Wine Night

 Fri, 13 Feb at 06:30 pm Vault Gallerie USD 61

LOVE & AFROBEATZ Chicago

 Sat, 14 Feb at 03:00 pm Bookclub Chicago USD 26 to 37

Valentine's Day After Party - Azul Rooftop Chicago

 Sat, 14 Feb at 10:00 pm Azul CAD 10 to 20

Valentine's Night — a Paint & Sip Experience to Remember

 Sat, 14 Feb at 05:30 pm Art City USD 110

Black Belt Eagle Scout

 Sat, 14 Feb at 06:00 pm The Empty Bottle

Cupid’s Castaway Karaoke

 Sat, 14 Feb at 05:00 pm Trader Todd's Free

Boolu House Music Red Party Feat DJ Stacy Kidd

 Sat, 14 Feb at 11:00 am Visions Odeum and Events USD 13 to 215

Catching Crabs for Valentine’s Day – Date Night Boil

 Fri, 13 Feb at 10:00 am The Crab Pad Free

VALENTINE'S DAY - SALSA FOR SINGLES - Chicago Edition

 Sat, 14 Feb at 06:00 pm Chicago - Jhoom Bar USD 15 to 34

Coach After Dark: Chicago

 Sat, 14 Feb at 09:00 pm Jackhammer USD 20 to 31

Trinket Fest Valentine’s Special

 Sat, 14 Feb at 12:00 pm 1750 N Milwaukee Ave Free

RATIO: ROSÉ LOUNGE

 Sat, 21 Feb at 03:00 pm Bodega Taqueria y Tequila USD 13 to 23

A Valentine's Dinner ft. The Sinatra Brothers

 Fri, 13 Feb at 06:30 pm Colvin House USD 18 to 151

Lovespell: Pole Dancing & Burlesque Show

 Sat, 14 Feb at 02:45 pm The Newport Theater USD 39 to 50

Chicago, IL - After Dark Divas Versus Night @ Punch Bowl Social

 Sat, 14 Feb at 09:00 pm Punch Bowl Social Chicago Free

Speed Dating Chicago | In-Person | Cityswoon | Ages 50-65

 Wed, 11 Feb at 07:30 pm Carnivale USD 43

Tropical Love Potion Night: Empanada + Mixology Class

 Sat, 14 Feb at 11:00 am Chicago Mama's Kitchen - Catering, Mixology & Culinary Experiences USD 37 to 120

Fri, 13th of Feb, 2026: Shimmer - Monthly Shoegaze/Dreampop Party- (my bloody) Valentine's Edition!

 Fri, 13 Feb at 09:00 pm DMen Tap

THE GENTLEMEN'S AFFAIR Presents Lovers Choice 2.0 Valentine's Day Party

 Sat, 14 Feb at 08:00 pm 2017 W Howard St USD 18 to 29

Galentine’s Night at Felix: Flowers, Cocktails & Modern Self-Love

 Thu, 12 Feb at 06:30 pm Felix: Modern American Dining USD 34

Valentine's Day Pizza Cooking Classes and Dinner

 Wed, 11 Feb at 06:00 pm Pizzeria Due USD 178

Valentine's Day "Dirty Dancing" Class 2026 - Chicago

 Fri, 13 Feb at 06:00 pm Duet Dance Studio USD 130

Hand-made Pasta and Lobster Class

 Sat, 14 Feb at 02:00 pm 3737 W Armitage Ave Free

Galen-Tini Night at The Lounge

 Fri, 13 Feb at 08:00 pm The Lounge Free

F*ck Love: Anti- Valentine's Drag Brunch

 Sun, 15 Feb at 01:00 pm Simone's USD 18

The Poetry Brothel: Devotion at Aloft Circus Arts

 Sat, 14 Feb at 08:00 pm Aloft Circus Arts

The Barr Brothers at Thalia Hall

 Sat, 14 Feb at 08:00 pm Thalia Hall

Heartbeat House Party

 Sat, 14 Feb at 07:00 pm 1200 S. DuSable Lake Shore Drive, Chicago, IL, United States, Illinois 60605

TorBeatle Los! play The Beatles With A Love Like That at The Tonk 2/14

Sat, 14 Feb at 08:00 pm Honky Tonk Bbq

Flash Class: Italian Caviar and Bubbles

 Sat, 14 Feb at 03:00 pm Eataly Chicago USD 107

Sip and Decorate: Vintage Cake Decorating Class

 Sat, 14 Feb at 01:00 pm RLM Studio USD 109 to 114

Club Brew: R&B Sound Experience(Valentines Singles Edition) @ Wake N Bakery

 Sat, 14 Feb at 04:00 pm Wake N Bakery Logan Square USD 18 to 29

Bahamas V-Day Cruise 2026

 Fri, 13 Feb at 01:00 pm Miami, FL

"NO LOVE LOST" (If You Outside for Valentine’s This the Move)

 Sat, 14 Feb at 10:00 pm Row 24 Chicago USD 0 to 120

Valentine’s Day Cacao Ceremony • Gong Wash • Ecstatic Dance Party

Sat, 14 Feb at 06:00 pm yogaview

Valentine’s Day - Battle of the Sexes - A Live Couples Game Show Experience

 Sat, 14 Feb at 08:45 pm 3641 S State St USD 135

Lola Kirke in Chicago, IL at Old School Town

 Sat, 14 Feb at 07:00 pm Old Town School of Folk Music

Valentine's Day Candle-Making Artisan Workshop (Saturday)

 Sat, 14 Feb at 05:00 pm Pilot Project Brewing - Logan Square USD 55

Latte art for beginners! (Valetine's Day edition)

 Sat, 14 Feb at 11:00 am 1806 W Cuyler Ave USD 86 to 107

Chicago Artisan Market

 Sat, 14 Feb at 11:00 am Artifact Events

Flash Class: Italian Caviar and Bubbles

 Thu, 12 Feb at 06:30 pm Eataly Chicago USD 107

Valentine’s Day SPEED DATING! — Single N Minglin® 4-Year Anniversary EVENT

 Sat, 14 Feb at 09:00 pm 6947 S South Chicago Ave USD 0 to 26

In-person class:Anti Valentine's Day Cookie Decorating (Chicago)

 Fri, 13 Feb at 06:30 pm Gateway To Learning (4925 N Lincoln Ave, Chicago, IL 60625) USD 65

Speed Dating Chicago | In-Person | Cityswoon | Ages 35-49

 Thu, 19 Feb at 07:30 pm La Bella Trattoria USD 43

2026 Valentine's Day Ball

 Sat, 14 Feb at 07:30 pm 4039B N Ravenswood Ave, 60613

Doggie Valentines Day Party

Fri, 13 Feb at 06:00 pm Park and Field

(L.O.L) Love or Lust

 Fri, 13 Feb at 08:00 pm Park Tavern USD 0 to 958

Valentine's Photoshoot PopUp

 Sat, 07 Feb at 12:00 pm Beermiscuous USD 10 to 15

Love Illustrated

 Wed, 11 Feb at 06:00 pm Davis Theater, Chicago USD 34 to 45

Sip & Dance: Valentine’s Night Edition

 Thu, 12 Feb at 07:00 pm BottlesUp! USD 55

Galentine's Day Portrait Painting Party

Fri, 13 Feb at 06:00 pm 4919 N Damen Ave, Chicago, IL 60625-1463, United States

Valentines Swing Class For Couples (West Loop)

 Fri, 13 Feb at 06:15 pm Ballroom Dance Chicago West Loop USD 107