Cocktails Events in Chicago

Check out happening cocktails events all around Chicago, IL

2026 Chicago Winter Tequila Tasting Festival (February 14) AE

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

St. Patrick's Day Lucky Charms River North Bar Crawl | Morning

 Sat, 14 Mar at 09:00 am 230 N Clark St USD 20 to 50

STAY GOLD ST. PADDY'S PARTY at Offshore Rooftop ☘️

 Sat, 14 Mar at 11:00 am Offshore Rooftop & Bar USD 29

St. Patrick's Day Chicago Green River Booze Cruise!

 Sat, 14 Mar at 11:30 am Chicago Lakefront Cruises USD 101 to 136

St Patrick's PALLOOZA 25+ Bars and Clubs Included

 Sat, 14 Mar at 08:00 am West Loop USD 13 to 66

St. Patrick's Day Evening Green River Cruise on Sat, March 14

 Sat, 14 Mar at 07:00 pm Anita Dee ONE Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) USD 30 to 59

St. Patrick's Day River Dyeing Cruise on Sat, March 14th (21+)

 Sat, 14 Mar at 09:00 am Anita Dee ONE Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) USD 40 to 112

St. Patrick's Day Lucky Charms Wicker Park Bar Crawl

 Sat, 14 Mar at 12:00 pm Wicker Park USD 19 to 60

St. Patrick's Day Lucky Charms Lincoln Park Bar Crawl

 Sat, 14 Mar at 12:00 pm Lincoln Park USD 14 to 60

ANNUAL: Irish You Were Here St Patty's OFFICIAL River North Bar Fest

 Sat, 14 Mar at 12:00 pm River North USD 14 to 3,523

St. Patrick's Day Late Morning Green River Cruise on Sat, March 14

 Sat, 14 Mar at 11:30 am Anita Dee ONE Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) USD 35 to 70

St. Patrick's Day Late Afternoon Green River Cruise on Sun, March 15

 Sun, 15 Mar at 04:30 pm Anita Dee ONE Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) USD 37 to 59

July 4th, Independence Day Cruise!

 Sat, 04 Jul at 04:30 pm Summer Of George USD 54 to 89

The R&B and Green River Cruise

 Sat, 14 Mar at 01:30 pm Island Party Boat USD 52 to 91

2026 Chicago Winter Tequila Tasting Festival (February 14)

 Sat, 14 Feb at 02:30 pm Downtown Chicago USD 0 to 440

Chicago Food Truck Festival, Season 13, "Summer Daisy Margarita Returns"

 Sat, 20 Jun at 10:00 am 2300 S Indiana Ave USD 0 to 87

St. Patrick's Day Afternoon Green River Cruise on Sun, March 15

 Sun, 15 Mar at 01:00 pm Anita Dee ONE Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) USD 37 to 59

St. Patrick's Day Lucky Charms River North Bar Crawl | Afternoon

 Sat, 14 Mar at 12:00 pm Headquarters Beercade USD 19 to 60

AirOtic Soirée Presents: LoveStruck (Chicago)

 Thu, 05 Feb Experience 868 USD 48 to 132

The Leprechaun's Den | Joy District Rooftop | 4 PM OPEN BAR

 Sat, 14 Mar at 04:00 pm Joy District USD 56 to 809

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

ST. PATRICK’S DAY RIVER DYEING VIEWING PARTY

 Sat, 14 Mar at 08:00 am 71 E Wacker Dr USD 247

St. Patrick's Day Lucky Charms Lake View Bar Crawl

 Sat, 14 Mar at 12:00 pm Lake View USD 19 to 60

St. Patrick's Day Friday Night River Cruise on Fri, March 13

 Fri, 13 Mar at 08:00 pm Anita Dee ONE Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) USD 26 to 42

Memorial Day Fireworks Booze Cruise!

 Sat, 23 May at 08:30 pm Summer Of George USD 43 to 66

St. Patrick's Day Chicago at Texan Taco Bar

 Sat, 14 Mar at 09:00 am Texan Taco Bar USD 41 to 214

Old Town “Paddy Access” Pass

 Sat, 14 Mar at 12:00 pm 1419 N Wells St USD 19

Taste of Ravenswood

 Fri, 06 Feb at 07:30 pm Ravenswood Event Center USD 98 to 1,069

Punch Palace

 Sat, 14 Feb at 06:00 pm Punch House USD 80

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

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

St. Patrick's Day Evening Green River Cruise on Tue, March 17

 Tue, 17 Mar at 06:00 pm Anita Dee ONE Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) USD 37 to 59

St. Patrick's Day Chicago River Dying Booze Cruise! Cruise Starts at 8:45am

 Sat, 14 Mar at 08:30 am Chicago Lakefront Cruises USD 118 to 176

LITTLE MISS DRAMA | The Cardi B Pregame

 Fri, 20 Mar at 10:00 pm Row 24 Chicago USD 0 to 180

Shamrock & Roll | Hubbard Inn | 4pm

 Sat, 14 Mar at 04:00 pm Hubbard Inn USD 56 to 109

Get Shamrocked Day Party | Joy District Rooftop | 12 PM OPEN BAR

 Sat, 14 Mar at 12:00 pm Joy District USD 62 to 1,806

Chicago Margarita Festival Season 12, "Summer Daisy Margarita Returns"

 Sat, 20 Jun at 10:00 am South Loop USD 10 to 66

Chicago Arte Agave Tequila and Mezcal Festival

 Fri, 29 May at 06:00 pm Artifact Events USD 86 to 114

St. Patrick’s Day Bash at The Bassment

 Sat, 14 Feb at 08:00 am The Bassment Free

St. Patrick's River Dancing at Rebar 2026

 Sat, 14 Mar at 08:00 am Rebar USD 82 to 2,563

Early Pour Club - TABLES FOR PURCHASE

 Sat, 14 Mar at 08:00 am Joy District USD 648

THE Madonna Drag Dinner

 Fri, 27 Feb at 06:00 pm Kit Kat Club USD 71

St. Pat's at The Godfrey Hotel Chicago

 Sat, 14 Mar at 08:00 am The Godfrey Hotel Chicago

Mexico in a Bottle Chicago 2026

 Sun, 26 Apr at 04:00 pm Bridgeport Art Center USD 72 to 89

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Sat, 14 Feb at 03:30 pm Studio W.I.P. USD 62

Sip Me, I'm Irish | Hubbard Inn | 12pm

 Sat, 14 Mar at 12:00 pm Hubbard Inn USD 56 to 109

St. Patrick's Day at Rebel & Rye - the best deal in Chicago!!

 Sat, 14 Mar at 09:00 am Rebel & Rye USD 38 to 50

Mardi Gras at Blue Bayou

 Sat, 14 Feb at 08:00 pm Blue Bayou USD 20

A Night of Green and Gold at Hubbard Inn | 8pm

 Sat, 14 Mar at 08:00 pm Hubbard Inn USD 13 to 23

Clover Club | 3rd Floor Hubbard Inn | 4pm

 Sat, 14 Mar at 04:00 pm Hubbard Inn USD 56 to 109

LOVE SUCKS - A VALENTINE'S DAY EXPERIENCE

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

Puppy Bowl XXII Viewing Party at Babe's Sports Bar!

 Sun, 08 Feb at 12:00 pm 3017 w armitage avenue

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Thu, 12 Feb at 08:30 pm Studio W.I.P. USD 62

TBD/TBD

 Sat, 04 Jul at 07:00 pm Kingston Mines - Chicago Blues Center USD 23

St. Patrick's Day at The Reveler

 Sat, 14 Mar at 09:00 am The Reveler USD 38 to 62

First Fridays Rock + Pop

 Fri, 06 Feb at 10:00 pm 2447 N. Milwaukee Avenue, Chicago, IL, United States, Illinois 60647

Mean Girls Bottomless Drag Brunch

 Sat, 28 Feb at 11:00 am Lark USD 76

St. Patricks Day | Parlay Lincoln Park | 10PM-12AM OPEN BAR

 Sat, 14 Mar at 10:00 pm Parlay Lincoln Park USD 50 to 66

PEEP SHOW: Chicago's Finest Burlesque Show!

 Fri, 09 Jan Stars and Garters Theater USD 30 to 40

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

Sun, 15 Feb at 12:00 am The Alston

Bottomless Mimosas on the Riverwalk - Every Weekend in Chicago

 Sat, 02 May at 11:00 am Island Party Hut (between Lake Shore Drive and Columbus on the Riverwalk) USD 31

Super Bowl Dinner and Drinks Spectacular Prix Fixe

 Sun, 08 Feb at 05:00 pm Kit Kat Club USD 71

Super Bowl Sunday Day Party

 Sun, 08 Feb at 04:00 pm Hue Chicago USD 0 to 119

Super Bowl LX Watch Party

 Sun, 08 Feb at 04:00 pm Hubbard Inn, West Hubbard Street, Chicago, IL, USA Free

Illinois vs MSU OPEN BAR

 Sat, 07 Feb at 07:00 pm Parlay Lincoln Park USD 50

Cinco De Mayo Bar Crawl - Chicago

 Sat, 02 May at 04:00 pm Bourbon on Division USD 20 to 76

Chicago Fireworks Booze Cruise!

 Sat, 25 Jul at 08:00 pm Summer Of George USD 43 to 66

Galentine's Night @ Era Social Club

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

Anita Dee II Dusable Harbor (TEMPLATE)

 Mon, 11 May at 08:00 pm Anita Dee II Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) USD 20 to 35

Heartthrob Throwbacks at Howl at the Moon Chicago

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

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Wed, 18 Mar at 06:00 pm Studio W.I.P. USD 62

Bottomless Margaritas & Fireworks on the Riverwalk - Every Weds & Sun!

 Wed, 03 Jun at 06:30 pm Island Party Hut (between Lake Shore Drive and Columbus on the Riverwalk) USD 25 to 58

Fashionista Drag Brunch

 Sat, 28 Feb at 11:00 am Kit Kat Club USD 79

SHE LOVES ME / NOT - Dorothy's Valentines Night

 Sat, 14 Feb at 06:00 pm Dorothy Free

Talk Agave To Me

 Sun, 22 Feb at 04:00 pm Lena Brava USD 60

Cupid’s Castaway Karaoke

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

Chicago, IL - Galentines Party! @ Punch Bowl Social

 Fri, 13 Feb at 07:00 pm Punch Bowl Social Chicago USD 15

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

Thursday | Meet Over Mezcal: Singles Social | Logan Square

Fri, 20 Feb at 01:00 am La Licor Panamericana

Wild Wander - Paint and Sip in Chicago | Classpop!™

 Fri, 06 Feb at 07:30 pm Pinot's Palette - Logan Square USD 56

2026 Chicago Summer Tequila Tasting Festival (July 25)

 Sat, 25 Jul at 02:30 pm TBA Downtown Chicago USD 0 to 440

TBD/TBD

 Sat, 23 May at 07:00 pm Kingston Mines - Chicago Blues Center USD 23

TBD/TBD

 Fri, 31 Jul at 07:00 pm Kingston Mines - Chicago Blues Center USD 23

Text Your Ex at Hubbard Inn

 Thu, 12 Feb at 08:00 pm Hubbard Inn USD 13

West Loop Margarita Fest | Margarita Tastings & Pizza Included

 Sat, 28 Feb at 12:00 pm PB&J: Pizza Beer and Jukebox USD 29 to 58

AMERICAN DREAMIN AFFAIR

 Sat, 28 Feb at 08:00 pm Rebar USD 34 to 61

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Tue, 17 Feb at 08:30 pm Studio W.I.P. USD 62

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Sat, 21 Mar at 08:30 pm Studio W.I.P. USD 62

Once Upon A Canvas: A Galentine’s Affair

 Fri, 13 Feb at 06:30 pm Sheraton Grand Chicago Riverwalk USD 53

Dads of Love Day Party

 Sun, 01 Mar at 02:00 pm Rizzo's Bar & Inn USD 0 to 73

City Reflections - Paint and Sip in Chicago | Classpop!™

 Fri, 06 Mar at 08:00 pm Pinot's Palette - Logan Square USD 56

St. Patrick's Day at Duffy's Tavern & Grille

 Sat, 14 Mar at 09:00 am Duffy's Tavern and Grille USD 56 to 68

SUNDAY FEBRUARY 22: CHICAGO'S BEST COMEDY SHOW

 Sun, 22 Feb at 07:00 pm The Comedy Bar - Chicago Main Stage Free

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Wed, 18 Feb at 06:00 pm Studio W.I.P. USD 62

Monet’s Water Lilies II - Paint and Sip in Chicago | Classpop!™

 Wed, 25 Feb at 07:00 pm Pinot's Palette - Logan Square USD 49

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Thu, 26 Feb at 08:30 pm Studio W.I.P. USD 62

Psychedelic Paradise - Paint and Sip in Chicago | Classpop!™

 Fri, 06 Feb at 08:00 pm Pinot's Palette - Logan Square USD 56

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

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

Love Is.... A Valentine Day Pop Up

 Thu, 12 Feb Row 24 Chicago USD 8 to 149

Chicago Rum Fest 2026

 Sat, 25 Apr at 02:00 pm Logan Square Auditorium USD 26 to 301