Cocktails Events in Chicago

Check out happening cocktails events all around Chicago, IL

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

4th of July Late Afternoon Cruise on Lake Michigan

 Sat, 04 Jul at 04:30 pm Anita Dee II Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) USD 20 to 42

July 4th, Independence Day Cruise!

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

4th of July Afternoon Cruise on Lake Michigan

 Sat, 04 Jul at 12:30 pm Anita Dee II Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) USD 20 to 42

80s vs 90s Night at the Zoo - An Adults Only Evening at Lincoln Park Zoo

 Sat, 19 Sep at 06:30 pm Lincoln Park Zoo USD 15 to 48

Chicago Fireworks Booze Cruise!

 Sat, 11 Jul at 08:00 pm Chicago Lakefront Cruises USD 43 to 66

'90s Night at the Zoo - Adults Only Evening at Lincoln Park Zoo

 Sat, 13 Jun at 06:30 pm Lincoln Park Zoo USD 15 to 48

Memorial Day Fireworks Booze Cruise!

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

July 3rd Premier Cruise Independence Celebration on Lake Michigan

 Fri, 03 Jul at 08:00 pm Anita Dee II Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) USD 25 to 47

Chicago Food Truck Festival, Season 13, "The Return of the Daisy"

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

Hip Hop Vs R&B All White Attire Yacht Party (3 Levels) Chicago

 Sun, 05 Jul at 06:45 pm Anita Dee Yacht Charters USD 50 to 535

The Boos & Booze Chicago Halloween Bar Crawl | Wicker Park

 Sat, 31 Oct at 02:00 pm Wrigleyville USD 8 to 31

Beach Slap North Ave Beach Party

 Sat, 13 Jun at 11:00 am North Avenue Beach USD 34 to 98

Fireworks Juneteenth Black Attire Yacht Party 3 Levels (Chicago)

 Sat, 20 Jun at 06:45 pm Anita Dee Yacht Charters USD 71 to 749

Fourth of July at IO Godfrey Rooftop

 Sat, 04 Jul at 04:00 pm IO Godfrey Rooftop Lounge USD 25

Chicago Arte Agave Tequila and Mezcal Festival

 Fri, 29 May at 06:00 pm Artifact Events USD 86 to 157

Reggaeton Beach Fest 2026 on Oak Street Beach

 Sun, 28 Jun at 03:00 pm Whispers at Oak Street Beach USD 24 to 527

The Halloween Bar Crawl - Chicago

 Sat, 31 Oct at 04:00 pm Kitchen + Kocktails By Kevin Kelley - Chicago USD 13 to 18

Chicago Margarita Festival Season 12, "The Return of the Daisy"

 Sat, 20 Jun at 10:00 am South Loop USD 13 to 66

White Attire Fireworks Yacht Cruise (Chicago) Anita Dee 2

 Sat, 23 May at 06:45 pm Anita Dee Yacht Charters USD 82 to 642

Old School House Yacht Party (3 Levels) Chicago

 Fri, 24 Jul at 06:45 pm Anita Dee Yacht Charters USD 50 to 642

WingOut Chicago 2026

 Sat, 26 Sep at 01:30 pm Gallagher Way Chicago

TOAST ALL WHITE CARIBBEAN YACHT PARTY: CHI PARTY WEEKEND 2026

 Sun, 21 Jun at 06:30 pm Anita Dee Yacht Charters USD 62 to 122

Air & Water Show Viewing Party - (Friday Preview | 8/14)

 Fri, 14 Aug at 11:00 am Shore Club USD 95 to 3,208

Chicago BYOB Exotic Paintings Sip and Paint with Male Models

 Fri, 13 May at 07:30 pm 5425 W Lawrence Ave USD 38

Chicago BYOB Sip and Paint with Male Models

 Sun, 03 Mar at 08:00 pm 5425 W Lawrence Ave USD 39

Memorial Day Weekend Night Lake Cruise on Sunday, May 24th

 Sun, 24 May at 08:00 pm Anita Dee II Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) USD 25 to 47

Pier Pressure Weekend

 Fri, 19 Jun at 10:00 am Navy Pier USD 31 to 260

Summer & Fall Afterwork Sunset Cruises on Lake Michigan

 Mon, 25 May at 07:30 pm Anita Dee II Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) USD 27 to 42

TBD/TBD

 Fri, 22 May at 07:00 pm Kingston Mines - Chicago Blues Center USD 23

Golden Hour Society: A Private Sunset Experience

 Sat, 27 Jun at 07:00 pm 1 E Wacker Dr floor 41 USD 114 to 149

Labor Day Weekend Fireworks Lake Cruise on Saturday, September 5th

 Sat, 05 Sep at 08:00 pm Anita Dee II Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) USD 30 to 58

CHAI RAVE CHICAGO: ALL-WHITE DAYTIMER ON JUNE 6 @ AZUL ROOFTOP!

 Sat, 06 Jun at 12:00 pm Azul USD 12

July 4th Weekend Kickoff Fireworks Booze Cruise!

 Wed, 01 Jul at 07:30 pm Summer Of George USD 31 to 54

La Vieja Escuela Perreo y Sazón

 Sat, 20 Jun at 12:30 pm Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location) USD 20 to 42

Saturday Night Fireworks Booze Cruise!

 Sat, 15 Aug at 08:30 pm Chicago Lakefront Cruises USD 49 to 95

The Chicago Pancakes & Booze Art Show (Vendor/Artist Reservations)

 Sat, 18 Jul at 08:00 pm Reggies

Baila Habibi حبيبي Summer Rooftop Party

 Sat, 20 Jun at 07:00 pm Azul USD 24 to 161

White Attire Fireworks River Cruise Yacht Party - Anita Dee 1

 Sat, 23 May at 07:30 pm Anita Dee Yacht Charters USD 50 to 322

Fireworks & Sunset Yacht Party 3 Levels (Chicago)

 Sat, 30 May at 06:45 pm Anita Dee Yacht Charters USD 61 to 642

Chinchorreo en Wrigleyville | Tix Include Brunch Buffet & 2 Shots!

 Sat, 27 Jun at 12:00 pm Wrigleyville's Best Bars TBA USD 16 to 28

Second Hand Soul Band | Chicago Taco & Tequila Fest | Wrightwood Park | Fri Jun 26th 6:30p

 Fri, 26 Jun at 06:30 pm 2555 N Ashland Ave, Chicago, IL 60614-2003, United States

Labor Day Weekend Evening Lake Cruise on Sunday, September 6th

 Sun, 06 Sep 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 42

Espresso Martini Fest at Hubbard Inn, Chicago - Tastings Included

 Sat, 03 Oct at 05:00 pm Hubbard Inn USD 25 to 42

Trending - Just Because 2026 Chicago Summer Holiday Bar Crawl

 Sat, 20 Jun at 04:00 pm Lincoln Park, River North, Wicker Park Bars All Access USD 0 to 8

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 25 to 31

The Official Halloween Bar Crawl - Chicago

 Sat, 31 Oct at 05:00 pm Black Hole Bar USD 17 to 86

MDW Rooftop Party at Offshore

 Sun, 24 May at 02:00 pm Offshore Rooftop USD 25

Saturday Night Labor Day Fireworks Booze Cruise!

 Sat, 05 Sep at 08:00 pm Chicago Lakefront Cruises USD 49 to 95

Whispers at Oak Street Beach | Juneteenth Day Party | 3PM–10PM

 Fri, 19 Jun at 03:00 pm Whispers at Oak Street Beach USD 34 to 217

The Boos & Booze Chicago Halloween Bar Crawl | West Loop

 Fri, 30 Oct at 05:00 pm Headquarters Beercade USD 14 to 43

OnlySundays Funday

 Sun, 24 May at 02:00 pm Hydrate Nightclub Free

Chicago Christmas in July Bar Crawl 2026

 Sat, 25 Jul at 06:00 pm PB&J: Pizza Beer and Jukebox USD 12 to 31

DILF: IML LEATHER DADDY

 Sat, 23 May at 09:00 pm The SoFo Tap Free

EL CALENTON PA' LA CULTURA: KICKOFF JANGUEO!

 Sun, 07 Jun at 12:00 pm Chicago Theater Works USD 14

Founding Price - 2026 Chicago Summer Tequila Tasting Festival (July 25)

 Sat, 25 Jul at 02:30 pm TBA Downtown Chicago USD 37 to 105

Just Announced - 2026 Chicago Summer Whiskey Tasting Festival (August 22)

 Sat, 22 Aug at 02:30 pm TBA Downtown Chicago USD 0 to 66

May 24th! Rooftop Sunday Funday Series Downtown!

 Sun, 24 May at 12:00 pm Reserv USD 0 to 429

Pride Makers Market at Hotel 55

 Sun, 14 Jun at 12:00 pm Hotel 55 Chicago Downtown Free

Executive DAY Order .. Day Party in Session

 Sun, 24 May at 03:00 pm City Hall (restaurant) - Chicago USD 0 to 269

SUNDAY FUNDAY

 Sun, 17 May at 03:00 pm ROOF on theWit Free

Chicago's Theatre of Magic at the Palmer House

 Sat, 13 Jun at 04:30 pm Palmer House a Hilton Hotel USD 59 to 99

Club Capri: Chicago's #1 Rooftop Party Series At Castaway's Beach Club

 Sat, 23 May at 02:00 pm Castaways Beach Club USD 31 to 78

Go Country Cruisin’ with Joe Nichols

 Tue, 10 Nov at 06:00 pm 600 E Grand Ave Chicago, IL

Pride Pole Night

 Fri, 26 Jun at 09:00 pm Provocateur USD 34 to 247

Chicago Fireworks Booze Cruise!

 Sat, 06 Jun at 08:00 pm Chicago Lakefront Cruises USD 45

Brews & Bites: The Ultimate Coffee & Chocolate Expo

 Sun, 14 Jun at 03:00 pm 3430 N Lincoln Ave USD 20 to 297

Chicago Fireworks Booze Cruise!

 Sat, 27 Jun at 07:30 pm Chicago Lakefront Cruises USD 45 to 65

Sunday Service at Shore Club Chicago

 Sun, 31 May at 11:00 am Shore Club USD 31

Dukes & Boots Skyline Yacht Party (3 Levels) Chicago

 Sun, 19 Jul at 06:45 pm Anita Dee Yacht Charters USD 50 to 535

Clean Up Your Act! - Solo Act Development Showcase

 Sun, 07 Jun at 07:00 pm The Newport Theater USD 23 to 34

Sunday Funday with Sexy Gogo Dancers - Boystown's Post Brunch Party

 Sun, 17 May at 02:00 pm Hydrate Nightclub Free

WE HATE CLUBS X FOREVER MINE X HENNESSY: OFFICIAL FESTIVAL AFTER-PARTY

 Sun, 24 May at 09:00 pm Expat USD 18

Date Night in River North | Cityswoon | Ages 33-45

 Thu, 21 May at 07:30 pm Machine Cocktail Bar USD 43

Wednesday | Dates for a Difference Singles Social | Carbon, West Loop

Thu, 21 May at 12:00 am Carbon

Bossa Nova Under the Stars at AIRE Rooftop

 Sun, 28 Jun at 05:00 pm Aire Rooftop USD 40 to 70

Chicago Exotic Paintings BYOB Wine and Paint Male Model

 Fri, 10 Mar at 09:00 pm 5425 W Lawrence Ave USD 39

The Whine Down : After Dark (Afro-caribbean bash)

 Sat, 06 Jun at 09:00 pm The Wild Hare & Singing Armadillo Frog Sanctuary USD 0 to 96

Kumbia Under The Stars

 Fri, 22 May at 08:00 pm Reserv USD 18 to 29

Yacht Rock Under the Stars at AIRE Rooftop

 Sun, 26 Jul at 05:00 pm Aire Rooftop USD 40 to 70

Bubbly & Beats - Memorial Day Weekend

 Sun, 24 May at 04:00 pm Hubbard Inn, West Hubbard Street, Chicago, IL, USA Free

Driven by Compassion: A Collective

 Fri, 29 May at 06:00 pm Porsche Downtown Chicago USD 0 to 162

Wamono: The Art of Japanese Rare Groove

 Thu, 25 Jun at 06:00 pm Kamehachi USD 55 to 108

SOS Latin Dance Fest — Night One

 Wed, 27 May at 07:00 pm 201 S. Ashland Avenue, Chicago, IL, United States, Illinois 60607

Memorial Day Fireworks Booze Cruise!

 Sat, 23 May at 08:00 pm Chicago Lakefront Cruises USD 45 to 55

Champagne Showers: The Ultimate Spring Party °⋆.ೃ࿔*:･

 Sat, 30 May at 08:00 pm Ambassador Gold Coast - The Chicago Hotel Collection USD 35 to 1,069

Mon Reve Fashion Showcase and Social Networking

 Thu, 25 Jun at 06:00 pm Azul USD 31 to 1,174

Summer Soirée: All-White Rooftop Networking Experience

 Thu, 11 Jun at 06:00 pm Aberdeen Crossing USD 0 to 61

Rising Stars Burlesque Revue

 Fri, 06 Mar at 08:00 pm Stars and Garters Theater USD 31 to 137

Holiday Weekend Kickoff! May 22nd! Friday Happy Hour Day Party @ Chemistry!

 Fri, 22 May at 03:00 pm Chemistry Chicago Free

Wild Flower Forest - Paint and Sip in Chicago | Classpop!â„¢

 Sat, 27 Jun at 03:00 pm Pinot's Palette - Logan Square USD 56

Chicago Exotic Paintings BYOB Sip and Paint with Male Models

 Fri, 26 Feb at 08:00 pm 5425 W Lawrence Ave USD 43

Dog's Night Out at Gallagher Way

 Fri, 31 Jul at 06:00 pm 3637 N Clark St, Chicago, IL, Chicago, IL, United States, Illinois 60613

Yellow Peril Drag Show

 Sat, 30 May at 06:00 pm Chinese American Museum of Chicago USD 30

Saturday Afternoon Booze Cruise!

 Sat, 15 Aug Chicago Lakefront Cruises USD 35 to 55

Psychedelic Starry Night - Paint and Sip in Chicago | Classpop!â„¢

 Thu, 16 Apr Pinot's Palette - Logan Square USD 49

Cubist Portrait - Paint and Sip in Chicago | Classpop!â„¢

 Thu, 23 Apr Pinot's Palette - Logan Square USD 49

Eventide - Paint and Sip in Chicago | Classpop!â„¢

 Sat, 23 May at 07:30 pm Pinot's Palette - Logan Square USD 56

2026 Chicago Mimosa Bar Crawl

 Sat, 23 May at 12:00 pm Royal Palms Shuffleboard Club USD 11 to 20

Yamazaki 18 & Cigar Pairing: A Symphony of Flavor and Elegance

 Sat, 09 May 3430 N Lincoln Ave USD 120