Chicago Food & Drink Events

African/Caribbean International Festival of Life (IFOL) - 33rd Annual.

Union Park 3 Jul 2026

Taste of Randolph 2026

900 West Randolph Street, Chicago, IL, United States, Illinois 60607 19 Jun 2026

Wells Street Art Festival 2026

West Division Street 13 Jun 2026

Belmont-Sheffield Music Festival

3200 N Sheffield Ave, Chicago, IL 60657-2211, United States 22 May 2026

Taste of Chicago

Chicago, Illinois, USA 11 Jul 2026

The 79th Annual 57th Street Art Fair: June 6–7, 2026

Hyde Park 6 Jun 2026

IFT FIRST 2026 Exhibition Booth Builder in Chicago

McCormick Place 12 Jul 2026

Old Town Art Fair 2026

Old Town 13 Jun 2026

2026 Windy City Smokeout - Saturday at Windy City Smokeout Festival

Windy City Smokeout Festival 11 Jul 2026

Adults Night Out: Block Party

N Cannon Dr at W Fullerton Pkwy, Chicago, IL, United States, Illinois 60614 22 May 2026

Zoo-ologie 2026

N Cannon Dr at W Fullerton Pkwy, Chicago, IL, United States, Illinois 60614 15 May 2026

Colombian Fest Chicago 2026

Humboldt Park 17 Jul 2026

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

2300 S Indiana Ave 20 Jun 2026

2026 Windy City Smokeout - Saturday at United Center

United Center 11 Jul 2026

Lincoln Park Mayfest

1000 W Armitage Ave, Chicago, IL 60614-4126, United States 15 May 2026

Beer Under Glass in Downtown Chicago

Harris Theatre @Millennium Park 8 May 2026

Taste of Northalsted Spring 2026

Northalsted 25 Apr 2026

Chicago Arte Agave Tequila and Mezcal Festival

Artifact Events 29 May 2026

Jazzin' at the Shedd

1200 S. DuSable Lake Shore Drive, Chicago, IL, United States, Illinois 60605 3 Jun 2026

10th Annual Juneteenth Black Bar Crawl Chicago

Jerk Villa Bar & Grill 20 Jun 2026

2026 Windy City Smokeout - Friday at Windy City Smokeout Festival

Windy City Smokeout Festival 10 Jul 2026

U2 Tribute at Lincoln Park's Mayfest - INTO THE HEART

1000 W. Armitage Ave., Chicago, IL 60614 16 May 2026

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

South Loop 20 Jun 2026

BRUNCH & R&B SPRING CRUISE

Anita Dee Yacht Charters 26 Apr 2026

FESTIVAL OF LIFE - Click Here for EARLY BIRD SPECIALS

Martin's International Special Events 3 Jul 2026

Sixteen Candles at LINCOLN PARK MAYFEST! **Racine Main Stage**

Mayfest 16 May 2026

MOTOBLOT #13 (Official)

Bridgeport, Chicago, Illinois 19 Jun 2026

Air & Water Show Oasis Viewing Party - (Saturday | 8/15)

Shore Club 15 Aug 2026

90s Forever Yacht Party (Chicago) 3 Levels

Anita Dee Yacht Charters 31 May 2026

Chicago Pickle Fest: Live Bands, Beer and Everything Pickle!

Wrigleyville's Best Bars 9 May 2026

Andersonville Wine Walk

Andersonville, Chicago, Il 17 May 2026

Kentucky Derby Party at ROOF on theWit: Derby Disco

ROOF on theWit 2 May 2026

Bottomless Mimosas on the Riverwalk - Every Weekend in Chicago

Island Party Hut (between Lake Shore Drive and Columbus on the Riverwalk) 2 May 2026

Mexico in a Bottle Chicago 2026

Bridgeport Art Center 26 Apr 2026

Chicago Spring Makers & Food Festival

Millennium Park Welcome Center 24 Apr 2026

Cinco De Mayo at Cafe Con Leche

Cafe Con Leche 5 May 2026

PILSEN'S CINCO DE MAYO BAR CRAWL PARTY!

Pilsen, Chicago, IL, USA 2 May 2026

Michelada Fest Chicago

Chicago 26 Jun 2026

World Famous Gospel Brunch at House of Blues (CHI)

House of Blues Chicago 10 May 2026

Double Treble Dueling Pianos @ Lincoln Park Mayfest - Sheffield & Armitage Stage

Mayfest 15 May 2026

Cinco De Drinko Rooftop Day Party

Utopian Tailgate 3 May 2026

Lincoln Square Greek Fest 2026

St. Demetrios Greek Orthodox Church 12 Jun 2026

Air & Water Show Viewing Party - (Sunday | 8/16)

Shore Club 16 Aug 2026

Gold Coast Art Fair (68th annual)

Grant Park 20 Jun 2026

Rodney Atkins Live on the Water!

600 E Grand Ave Chicago, IL 30 May 2026

Second Hand Soul Band | Chicago Mayfest | Lincoln Park | Sun May 17th 3p

1000 W Armitage Ave, Chicago, IL 60614-4126, United States 17 May 2026

Lincoln Park Greek Fest

2701 N Sheffield Ave, Chicago, IL, United States, Illinois 60614 6 Jun 2026

Good Company x Black Yacht Weekend: Beach Fest Juneteenth Celebration

Whispers at Oak Street Beach 20 Jun 2026

TBD/TBD

Kingston Mines - Chicago Blues Center 23 Apr 2026

Munch March Dessert & Appetizer Crawl

A variety of Ravenswood small businesses 22 Apr 2026

Millennium Art Festival

Michigan Ave & E Lake St, Chicago 27 Jun 2026

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

2555 N Ashland Ave, Chicago, IL 60614-2003, United States 26 Jun 2026

R&B BRUNCH

200 N Breakwater Access 3 May 2026

Hoppin’ JoJo’s Spring Fling

Stolen Saddle 15 May 2026

Sixteen Candles at LINCOLN PARK GREEK FEST!

St George Greek Orthodox Church of Chicago 5 Jun 2026

Taco Tuesday Again! Cinco De Mayo EDITION

Avondale Music Hall 5 May 2026

Mothers Day, Hands-On: Filled Pasta Roses

Eataly Chicago 9 May 2026

SATURDAY APRIL 25: CHICAGO'S BEST COMEDY SHOW

The Comedy Bar - Chicago Main Stage 25 Apr 2026

Brunch con Ritmo: Brunch & Dance Floor Experience

702 West Fulton Street, West Loop, Chicago, IL, United States, Illinois 60661 24 May 2026

ABBA Mamma Mia Drag Dinner

Kit Kat Club 8 May 2026

World Famous Gospel Brunch at House of Blues (CHI)

House of Blues Chicago 10 May 2026

Mother's Day Brunch Buffet With a View

Trump International Hotel & Tower® Chicago 10 May 2026

Singles Migle Mixer Barcocina Lakeview

Barcocina Lakeview 28 Apr 2026

Lincoln Roscoe Art + Craft Fair

3329 N Lincoln Ave 16 May 2026

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

Shore Club 14 Aug 2026

Hands-On: Spaghetti alla Carbonara

Eataly Chicago 23 Apr 2026

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

Island Party Hut (between Lake Shore Drive and Columbus on the Riverwalk) 3 Jun 2026

Chicago African Restaurant Week 2026

Chicago 15 Oct 2026

The Great Gatsby Boat Party

112 E Wacker Dr 16 May 2026

I|O Godfrey Kentucky Derby Viewing Event 2026

I|O Godfrey Rooftop Lounge 2 May 2026

Millennium Art Festival

180 N Stetson Ave 27 Jun 2026

Third Coast Tattoo Show 2026

Morgan MFG 26 Jun 2026

Chicago Whiskey Washback

Artifact Events 26 Jun 2026

Chicago Rum Fest 2026

Logan Square Auditorium 25 Apr 2026

Brews & Bites: The Ultimate Coffee & Chocolate Expo

3430 N Lincoln Ave 25 Apr 2026

Mother's Day Hands-On: Ravioli and Filled Pastas with Brunch Buffet

Eataly Chicago 10 May 2026

Pride & Provisions

Center on Halsted 7 Jun 2026

Chicago African Restaurant Week Festival 2026

TBA 10 Oct 2026

AICP Midwest's 2026 MEET.DRINK.TALK

Tunnel 14 May 2026

Eataly & The Second City: Eat, Laugh, Love

Eataly Chicago 25 Apr 2026

A Taste of Spain! Pintxos with Chef Marcos Campos! 🍽️🌎

40 S Halsted St, Chicago, IL 60661-3506, United States 14 May 2026

3rd Annual Taste of Bronzeville

3701 S Martin Luther King Dr 25 Jul 2026

Spectator Pass - Checkeditout 2026: The Chicago Porsche Convergence

Location: TBA 22 Aug 2026

Spring Wine Stroll 2026

Lincoln Square Ravenswood neighborhood 7 May 2026

Chef’s Dinner: Primavera

Eataly Chicago 16 May 2026

ECI TUESDAY MAMBO SALSA BACHATA & MORE at PIER 31 - 2026 (Year 12)

Pier 31 26 May 2026

2026 Chicago Top Shelf Tequila and Whiskey Tasting Festival (Sept 26)

Downtown Chicago 26 Sep 2026

Ambassador Room Mother's Day Grand Brunch

Ambassador Gold Coast - The Chicago Hotel Collection 10 May 2026

Derby After Dark at The Bassment

The Bassment 2 May 2026

Espresso Martini Fest at Hubbard Inn, Chicago - Tastings Included

Hubbard Inn 3 Oct 2026

Equality and Pride 365 2026

IO Godfrey 12 Jun 2026

Make Potstickers From Scratch - Cooking Class in Chicago | Classpop!™

Wolf Point Distilling 23 Apr 2026

2026 Chicago Summer Tequila Tasting Festival (July 25)

TBA Downtown Chicago 25 Jul 2026

SummerSalt Market

The Salt Shed Outdoors (Fairgrounds) 31 May 2026

Alhambra Palace Mother's Day Brunch 2026

1240 W Randolph Street 10 May 2026

Maifest

Goose Island Salt Shed Pub 2 May 2026

My Happiest Hour - Paint and Sip in Chicago | Classpop!™

Pinot's Palette - Logan Square 26 Apr 2026

Sazón Latin Food Festival 2026: Chicago’s Taste of Latin American Food

KOVAL Store 14 Jun 2026

Munch March Dessert & Appetizer Crawl

BienMeSabe Venezuelan Cafe & Restaurant 22 Apr 2026

Mother's Day in Somerset

Somerset 10 May 2026