Chicago Valentine's Day Events

2026 Chicago Winter Tequila Tasting Festival (February 14) AE

Kings Dining & Entertainment 14 Feb 2026

Motion City Soundtrack with Say Anything

Riviera Theatre - Chicago 14 Feb 2026

AirOtic Soirée Presents: LoveStruck (Chicago)

Experience 868 5 Feb 2026

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

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

The Outsiders at Cadillac Palace

Cadillac Palace 10 Feb 2026

Lyric Opera of Chicago: Cosi Fan Tutte

Lyric Opera House - IL 31 Jan 2026

3rd Annual All 80's Prom

Theater on the Lake 14 Feb 2026

Raks Inferno: A Valentine Speakeasy

The Newport Theater 13 Feb 2026

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

Good Night John Boy 14 Feb 2026

Valentine's Day at NoMI Kitchen

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

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

Stereo Nightclub 6 Feb 2026

FiREHAUS: In Heat

3352 N Halsted St 14 Feb 2026

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

Experience 868 Events 5 Feb 2026

Old Crow's Anti-Valentine's Day Party

Old Crow Smokehouse 14 Feb 2026

Valentine’s Days Speed Dating Event

Chicago's Downtown 14 Feb 2026

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

The Lincoln Lodge 14 Feb 2026

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

Hopsmith Chicago 13 Feb 2026

Not Ur Baby

Replay Lincoln Park 14 Feb 2026

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

Eataly Chicago 14 Feb 2026

Valentine's Day Festa

Eataly Chicago 13 Feb 2026

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

Get in the Kitchen 14 Feb 2026

Cupid’s Castaway Karaoke

Trader Todd's 14 Feb 2026

Boolu House Music Red Party Feat DJ Stacy Kidd

Visions Odeum and Events 14 Feb 2026

RATIO: ROSÉ LOUNGE

Bodega Taqueria y Tequila 21 Feb 2026

Lovespell: Pole Dancing & Burlesque Show

The Newport Theater 14 Feb 2026

The Barr Brothers at Thalia Hall

Thalia Hall 14 Feb 2026

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

Punch Bowl Social Chicago 14 Feb 2026

The Poetry Brothel Chicago: DEVOTION

Aloft Circus Arts 14 Feb 2026

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

Duet Dance Studio 13 Feb 2026

A Valentine's Dinner ft. The Sinatra Brothers

Colvin House 13 Feb 2026

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

Felix: Modern American Dining 12 Feb 2026

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

Simone's 15 Feb 2026

Flash Class: Italian Caviar and Bubbles

Eataly Chicago 14 Feb 2026

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

Honky Tonk Bbq 14 Feb 2026

Bahamas V-Day Cruise 2026

Miami, FL 13 Feb 2026

Doggie Valentines Day Party

Park and Field 13 Feb 2026

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

La Bella Trattoria 19 Feb 2026

Valentine's Day Candle Making Workshop and Dining Experience

Pullman Artspace Lofts 13 Feb 2026

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

1806 W Cuyler Ave 14 Feb 2026

Galentine's Day Portrait Painting Party

4919 N Damen Ave, Chicago, IL 60625-1463, United States 13 Feb 2026

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

Gateway To Learning (4925 N Lincoln Ave, Chicago, IL 60625) 13 Feb 2026

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

6947 S South Chicago Ave 14 Feb 2026

2026 Valentine's Day Ball

4039B N Ravenswood Ave, 60613 14 Feb 2026

Love, Cre8ives 2: An R&B Music Fest

BASSLINE || 2239 - CHICAGO 15 Feb 2026

Valentine's Eve Dinner & Dancing: Make Tapas & Learn to Salsa Dance

Get in the Kitchen 13 Feb 2026

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

Get in the Kitchen 15 Feb 2026

Valentine's Day Partner Yoga & Sound Bath

The Sanctuary Yoga Studio 14 Feb 2026

Sugarcane Jane Presents: The Full Tilt Burlesque Show

Emporium Wicker Park 13 Feb 2026

a love ain't DIRT or CHEAP WINE tasting

middle brow - bungalow 12 Feb 2026

Valentines Swing Class For Couples (West Loop)

Ballroom Dance Chicago West Loop 13 Feb 2026

HandPicked’s Presents Whispers in the Dungeon

A HandPicked Venue 14 Feb 2026

Valentines Country Dance Class For Couples (West Loop)

Ballroom Dance Chicago West Loop 14 Feb 2026

Valentines Salsa Class For Couples (West Loop)

Ballroom Dance Chicago West Loop 14 Feb 2026

The Shops - Valentines Day Edition

Water Tower Place (Level 3 Next to JJill and White House Black Market) 15 Feb 2026

Love Notes Live - Feat. Slique J. Adams & MoFitz Project

Haven Entertainment Center 13 Feb 2026

A Date Night Dining Experience Featuring Island Tings

1105 W Chicago Ave 14 Feb 2026

Faith Over Fear Valentine Sip & Paint

K’LAB Bronzeville 14 Feb 2026

Performance: BLIND LOVE - Valentine's Day with Rapt In Plastic

International Museum of Surgical Science 14 Feb 2026

SPREAD THE LOVE: VALENTINE'S DAY JEWELRY MARKET

The Center of Order and Experimentation 14 Feb 2026

Valentine’s Day Ceramic Mug and a Bowl

1142 W 18th St 14 Feb 2026

Swingin' Sweetheart's Dance with the Rhythm Rockets

Frankie's Blue Room 14 Feb 2026

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

Row 24 Chicago 14 Feb 2026

IMSS 4th Annual Speed Friending

International Museum of Surgical Science 13 Feb 2026

"A Pizza My Heart" Valentine's Day Cooking Class

Bettie's Chicago 11 Feb 2026

Opal the Opossum Kissing Booth Photoshoot and Pet Toy Drive

The Insect Asylum 13 Feb 2026

A Purse-onable Valentine Workshop

2040 N Elston Ave 13 Feb 2026

Valentines Day Ball

Ballroom Dance Chicago 14 Feb 2026

ST. VALENTINE'S DAY MASSACRE @ Underground Lounge, Saturday February 14

Underground Lounge - Chicago 14 Feb 2026

Valentine's Day Partner Yoga & Sound Bath

The Sanctuary Yoga Studio 13 Feb 2026

Eureka Day at Broadway Playhouse at Water Tower Place

Broadway Playhouse at Water Tower Place 13 Jan 2026

Do Not Disturb: Ritz Paris

Experience 868 Events 21 Feb 2026

Heartbeat House Party

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

Galentine's Fashion Show

The Colette Collection 1 Feb 2026

Post-Valentine’s Cacao Ceremony: Cultivating Self-Love

Northshore Healing Centre 15 Feb 2026

Rituals of Love: A Valentine’s Flower Workshop

SALTEATR STUDIO 13 Feb 2026

Snoopy Sip and Paint in Chicago

Mirella’s Tavern 23 Jan 2026

Dark Romance: A Low-Key Valentine’s Candle Night

Color Cocktail Factory 14 Feb 2026

Chicago Valentine Social

Union League Club 14 Feb 2026

Workshop: Japanese Papermaking

International Museum of Surgical Science 14 Feb 2026

Galentine’s ParTea Entertaining Experience

Bronze47 7 Feb 2026

Galentine’s Day Party & Happy Hour

Parlay River North 13 Feb 2026

Terrapin Flyer Mardi Gras Weekend

3855 N Lincoln Ave, Chicago, IL, United States, Illinois 60613 14 Feb 2026

Chicago Valentine’s Day Date Night on the Wheel **BYOB**

1142 W 18th St 14 Feb 2026

Valentine Speed Dating at Lou Malnalti Pizza

3859 W Ogden Ave 13 Feb 2026

Flow with Love: A Sound & Vibrational Journey

The Space Community Studio 14 Feb 2026

Coupled 2 Create: Sand Art Edition (2 timeslots)

KaLab Bronzeville 19 Feb 2026

Parents Night Out: Valentine Edition

1750 N Clark St 13 Feb 2026

Venus + Mars

4042 N Pulaski Rd 14 Feb 2026

Valentine's Day Sound Bath + Cacao

Wildlight Yoga 14 Feb 2026

Paint & Sip: Galentine's Painting Party! (Valentine's Theme)

545 N Dearborn St 12 Feb 2026

Get Lit: Rom Com Night

American Writers Museum 10 Feb 2026

Kaia String Quartet and Fareed Haque | Sculptor Margie Criner

Artifact Events 15 Feb 2026

Steakhouse Classics Cooking Class

Bettie's Chicago 14 Feb 2026

Tragic Love: Pole Night

Provocateur 13 Feb 2026

Comedy Uninterrupted Presents LIVE COMEDY at Theory's sports lounge

9 W Hubbard St 11 Feb 2026

SWEET, LIES, VALENTINE! *Valentine's Dessert Lie Detector Night! 18+ Only!*

208 E 79th St 12 Feb 2026

Steakhouse Classics Cooking Class

Bettie's Chicago 13 Feb 2026

Suminagashi - Ink Marbling Workshop

Heritage Museum of Asian Art 14 Feb 2026

In-person class:Valentines Day Cookie Decorating(Chicago)

Chef's place (The full address will be provided in the confirmation email after purchase) 14 Feb 2026

Valentines Couples Candlelight Stretch

Chicago Aerial Arts 15 Feb 2026