312Caribbean logoChicago • June 2026

CHICAGOCaribbean Heritage Month

Caribbean Vibe. Midwest Hustle.

From networking to nightlife, from parade energy to the Expo — experience the best of Caribbean Chicago in one place.

⚡ Events fill fast — don't miss your spot

Explore the Events

The Lineup

Calendar of Events

Sundays at Baseline flyer
Nightlife

Sundays at Baseline

Weekly2239 S Michigan Ave, Chicago

Weekly Caribbean nightlife experience in Chicago.

Flyer
Southside Networking flyer
Networking

Southside Networking

Wednesday, June 3, 2026Uncle Joe's Rum Bar & Grill, 1450 S Michigan Ave, Chicago

Connect with Caribbean entrepreneurs

Northside Networking flyer
Networking

Northside Networking

Wednesday, June 17, 2026D'Cuba, Chicago

Build, connect, and grow

Chi Party Weekend flyer
Weekend

Chi Party Weekend

June 19–21, 2026Chicago

3-day Caribbean party experience — rooftop vibes, live DJs, and an all-white boat ride.

Flyer
Puerto Rico vs Jamaica Domino Showdown flyer
Domino Tournament

Puerto Rico vs Jamaica Domino Showdown

Saturday, June 27, 2026Melrose Park, IL

Battle for 1 Year of Bragging Rights. The Puerto Rican squad has officially called out the Jamaicans for a high-energy domino showdown at the Expo. Bring your team, represent your island, and compete for ultimate bragging rights.

Expo & Marketplace flyer
FeaturedCancelled

Expo & Marketplace

June 27, 2026Melrose Park, IL

Food, Culture, Music & Shopping.

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Community Partners

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Proudly supported by Caribbean-owned businesses helping us build something bigger for the culture.

D'Cuba Authentic Cuban Cuisine logo
Uncle Joe's Rum Bar & Grill logo

Where Chicago Meets
The Caribbean