Chicago Cigar Week Events 2026
About this Event
Chicago Cigar Week is more than a series of events—it’s a celebration of premium cigars, elevated nightlife, live entertainment, fashion, networking, and unforgettable experiences. Join us July 24–26 for three signature events showcasing the very best of Chicago’s cigar and social culture.
NOIR, ASH & COCKTAILS
A Black Affair
Friday, July 24 | 8:00 PM – 1:00 AM
Sal’s on Tap | 1645 W. Jackson Blvd. | Chicago
Event Description
Chicago Cigar Week begins with an evening of sophistication, style, and elevated nightlife.
Join us for Noir, Ash & Cocktails, an elegant All Black Affair where premium cigars, handcrafted cocktails, great music, and beautiful people come together for an unforgettable night.
Dress in your finest black attire and experience an intimate evening designed for cigar lovers, professionals, and those who appreciate luxury.
Hosted by Christine Morgan
Music By
Leon Rogers
DJ Sirprize
Special Guest
Distinguished 3B
Whether you’re lighting your favorite cigar, enjoying a signature cocktail, or simply taking in the atmosphere, this is the perfect way to kick off Chicago Cigar Week.
Attire: All Black Chic
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SUMMER SIP & SMOKE
A Summertime Chi Courtyard Affair
Saturday, July 25 I Noon-8:00 pm
DuSable Black History Museum Courtyard
740 E. 56th Place • Chicago
Event Description:
Experience one of the most anticipated outdoor events of the summer as Chicago Cigar Week transforms the beautiful DuSable Museum Courtyard into an afternoon of live entertainment, premium cigars, cocktails, food, and unforgettable vibes.
Surrounded by beautiful landscaping and open-air elegance, enjoy an incredible lineup of legendary performers and DJs while relaxing with friends in one of Chicago’s most unique outdoor settings.
Live Performances
Crucial Conflict
Terisa Griffin (performing her hit “Wonderful”)
Steppin’ w/George Daniels
Featuring:
Slique Jay Adams
Danny Boy
Music By:
Boolu Master
DJ Pharris
Also Featuring:
DJ Freeze (Dallas)
Kevin “KB” Burns
Whether you’re dancing, stepping, smoking a premium cigar, or simply soaking in the summer atmosphere, this is where Chicago comes together during Cigar Week.
Bring your lawn chair, your crew, and your summertime energy.
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DRAKE DAY
Head to Taupe
Sunday, July 26 | Noon – 4:00 PM
The Drake Hotel Oak Brook
2301 York Road • Oak Brook
Event Description:
Close out Chicago Cigar Week in style at one of Chicagoland’s most elegant destinations.
Join NBA Hall of Famer Tim Hardaway for an unforgettable afternoon of premium cigars, brunch cocktails, beautiful people, and sophisticated vibes on the stunning outdoor terrace of The Drake Hotel Oak Brook.
This year’s fashion theme is:
HEAD TO TAUPE:
Dress in elegant shades of:
Cream, Ivory, Beige, Camel, Tan, Cognac
Mocha, Chocolate Brown
The afternoon blends luxury fashion, premium cigars, handcrafted cocktails, and great music into one signature summer experience.
Hosted by:
NBA Hall of Famer Tim Hardaway
Co-Hosts: Ebony Beatle & Harold Dorsey
Music By
Mark Fuller
Kevin Burns
DJ ROC
Gather your friends, dress to impress, and enjoy the perfect finale to Chicago Cigar Week.
Attire: Upscale Chic — Shades of Cream, Tan & Brown (“Head to Taupe”)
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https://www.youtube.com/shorts/JVAaRofLlbo
Where is it happening?
USD 12.51 to USD 172.57
