Chicago Valentine's Day Events

CHICAGO BOLLYWOOD VALENTINES NIGHTOUT @FAME NIGHTCLUB

Lore Chicago 13 Feb 2026

2026 Chicago Winter Tequila Tasting Festival (February 14) AE

Kings Dining & Entertainment 14 Feb 2026

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

Burnham Harbor S Dock (Anita Dee 2) 14 Feb 2026

Motion City Soundtrack with Say Anything

Riviera Theatre - Chicago 14 Feb 2026

The Outsiders at Cadillac Palace

Cadillac Palace 10 Feb 2026

10th Annual: Anti-Valentines Day Valentines Day Crawl

River North 14 Feb 2026

Chaotic Singles VALENTINE'S Party! (Chicago)

Joy District 13 Feb 2026

LOVE IS IN THE ATMOSPHERE

Adler Planetarium 7 Feb 2026

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

ROOF on theWit 15 Feb 2026

AirOtic Soirée Presents: LoveStruck (Chicago)

Experience 868 5 Feb 2026

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

VU Rooftop Bar 15 Feb 2026

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

Stereo Nightclub 6 Feb 2026

3rd Annual All 80's Prom

Theater on the Lake 14 Feb 2026

PlayDates Brunch and Day Party

Punch Bowl Social 14 Feb 2026

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

Smartbar Chicago 15 Feb 2026

Raks Inferno: A Valentine Speakeasy

The Newport Theater 13 Feb 2026

Chef's Valentines Dinner: Italian Date Night

Eataly Chicago 14 Feb 2026

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

Good Night John Boy 14 Feb 2026

IRL: Heated Rivalry Singles Mixer!

Dorothy 9 Feb 2026

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

Wild Blossom Meadery and Winery 14 Feb 2026

House Vs Reggaeton Dance Party (The Battle Valentines Edition)

Simone's 14 Feb 2026

Valentine's Candlelight Jazz Tribute to Luther Vandross feat. Peter Jordan

Reva and David Logan Center for the Arts 14 Feb 2026

¡Pachanga! Amor Vaquero on Navy Pier

Bar Sol 14 Feb 2026

Valentine's Day at NoMI Kitchen

800 N Michigan Ave, Chicago, IL 60611 14 Feb 2026

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

Bar Moxy 14 Feb 2026

Valentine's Murder Mystery Dinner

Olive Black Chicago 14 Feb 2026

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

Experience 868 Events 5 Feb 2026

FiREHAUS: In Heat

3352 N Halsted St 14 Feb 2026

Lyric Opera of Chicago: Cosi Fan Tutte

Lyric Opera House - IL 31 Jan 2026

Mardi Gras at Blue Bayou

Blue Bayou 14 Feb 2026

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

Hubbard Inn 14 Feb 2026

Valentine's Day 2026 at Alhambra Palace Chicago

1240 W Randolph Street 14 Feb 2026

Pamper Your Pup Valentine's Day Event

Bosly's Backyard 15 Feb 2026

Old Crow's Anti-Valentine's Day Party

Old Crow Smokehouse 14 Feb 2026

Chicago Galentine’s Wine Tasting Experience | Hotel 55 & Lure Fishbar

Lure Fishbar - Chicago 13 Feb 2026

LOVE SUCKS - A VALENTINE'S DAY EXPERIENCE

Ambassador Gold Coast - The Chicago Hotel Collection 14 Feb 2026

Valentine's Day at Hopsmith

Hopsmith Chicago 14 Feb 2026

TUFF LOVE feat. Rika B, Mayya & Muffy

646 N Franklin St, Chicago, IL 14 Feb 2026

Hubbard Inn Uncorked Galentine's Edition

Hubbard Inn 13 Feb 2026

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

Chalet 13 Feb 2026

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

The Lincoln Lodge 14 Feb 2026

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

Get in the Kitchen 14 Feb 2026

Galentine's Night @ Era Social Club

Era Social Club 14 Feb 2026

Valentine’s Days Speed Dating Event

Chicago's Downtown 14 Feb 2026

Not Ur Baby

Replay Lincoln Park 14 Feb 2026

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

Hopsmith Chicago 13 Feb 2026

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

The Alston 15 Feb 2026

Cupid's House Party at Electric Shuffle Chicago

Electric Shuffle Chicago 13 Feb 2026

Valentine's Day Festa

Eataly Chicago 13 Feb 2026

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

Eataly Chicago 14 Feb 2026

Valentine's Painting + Wine Night

Vault Gallerie 13 Feb 2026

Boston Richey Live in Chicago – Valentine’s Day Weekend

V Live Restaurant & Live Music Entertainment 15 Feb 2026

Hands-On: Tiramisù alla Fragole, Valentines Edition

Eataly Chicago 15 Feb 2026

Heartthrob Throwbacks at Howl at the Moon Chicago

Howl at the Moon Chicago 13 Feb 2026

SHE LOVES ME / NOT - Dorothy's Valentines Night

Dorothy 14 Feb 2026

Valentine's Day After Party - Azul Rooftop Chicago

Azul 14 Feb 2026

Cupid’s Castaway Karaoke

Trader Todd's 14 Feb 2026

Black Belt Eagle Scout

The Empty Bottle 14 Feb 2026

LOVE & AFROBEATZ Chicago

Bookclub Chicago 14 Feb 2026

Boolu House Music Red Party Feat DJ Stacy Kidd

Visions Odeum and Events 14 Feb 2026

Valentine's Friday 2026 at Alhambra Palace Chicago

1240 W Randolph Street 13 Feb 2026

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

Art City 14 Feb 2026

One Direction Dance Party x Valentines Day with DJ Kenny Braasch & DJ Real Co

Joe's on Weed Street 14 Feb 2026

Catching Crabs for Valentine’s Day – Date Night Boil

The Crab Pad 13 Feb 2026

VALENTINE'S DAY - SALSA FOR SINGLES - Chicago Edition

Chicago - Jhoom Bar 14 Feb 2026

Coach After Dark: Chicago

Jackhammer 14 Feb 2026

Trinket Fest Valentine’s Special

1750 N Milwaukee Ave 14 Feb 2026

RATIO: ROSÉ LOUNGE

Bodega Taqueria y Tequila 21 Feb 2026

Foodsprung’s Smash Sesh “Side Piece Edition”

Frontier Chicago 22 Feb 2026

Text Your Ex at Hubbard Inn

Hubbard Inn 12 Feb 2026

A Valentine's Dinner ft. The Sinatra Brothers

Colvin House 13 Feb 2026

Lovespell: Pole Dancing & Burlesque Show

The Newport Theater 14 Feb 2026

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

Carnivale 11 Feb 2026

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

Punch Bowl Social Chicago 14 Feb 2026

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

Felix: Modern American Dining 12 Feb 2026

Valentine's Day Pizza Cooking Classes and Dinner

Pizzeria Due 11 Feb 2026

Hand-made Pasta and Lobster Class

3737 W Armitage Ave 14 Feb 2026

Galen-Tini Night at The Lounge

The Lounge 13 Feb 2026

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

2017 W Howard St 14 Feb 2026

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

Duet Dance Studio 13 Feb 2026

Heartbeat House Party

1200 S. DuSable Lake Shore Drive, Chicago, IL, United States, Illinois 60605 14 Feb 2026

Tropical Love Potion Night: Empanada + Mixology Class

Chicago Mama's Kitchen - Catering, Mixology & Culinary Experiences 14 Feb 2026

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

Simone's 15 Feb 2026

SIP & RNB Social

Reserv 12 Feb 2026

The Barr Brothers at Thalia Hall

Thalia Hall 14 Feb 2026

Flash Class: Italian Caviar and Bubbles

Eataly Chicago 14 Feb 2026

The Poetry Brothel: Devotion at Aloft Circus Arts

Aloft Circus Arts 14 Feb 2026

Mix, Mingle, & Maybe: A Social Valentine Experience

70 E Pershing Rd suite 1w 13 Feb 2026

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

Wake N Bakery Logan Square 14 Feb 2026

Sip and Decorate: Vintage Cake Decorating Class

RLM Studio 14 Feb 2026

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

DMen Tap 13 Feb 2026

Lola Kirke in Chicago, IL at Old School Town

Old Town School of Folk Music 14 Feb 2026

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

yogaview 14 Feb 2026

Bahamas V-Day Cruise 2026

Miami, FL 13 Feb 2026

Valentine's Day Worship Night!

1543 W Howard St 14 Feb 2026

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

3641 S State St 14 Feb 2026

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

Row 24 Chicago 14 Feb 2026

Corazones in the Gallery

National Museum of Mexican Art 13 Feb 2026

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

1806 W Cuyler Ave 14 Feb 2026

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

Pilot Project Brewing - Logan Square 14 Feb 2026