Real Jazz, Real Pizza, Real Authentic

live Music nightly!

“Music gives a soul to the universe, wings to the mind, flight to the imagination, and life to everything.”


Born out of our love of fine cigars, fine wines and good music, Chicagos has become the exclusive Dinner club in Key West. After traveling the world and experiencing different musical cultures, we decided to make our way back to Key West bringing Motown, Jazz and Blues music for all to enjoy. Featuring local talent as well as well-known artists, we offer live music every night of the week. At Chicagos, every hour is Happy Hour. Come and relax. Listen to great music, enjoy a couple of drinks have the freshest Cigar in the Keys with your friends or colleagues. and experience our love of Motown, Jazz and Blues music for yourself.




Whether it's a private party or our signature Latin Night, Chicagos is the perfect venue for any good time.


City Culture
Old World Class
Proprietary Blend

Menu Highlights



Bringing a flavor once lost to your memories now

step into a new scene from an old time

Chicagos has a vision. Its one born from years of both owners looking at the world in ways that people simply don't usually see it. Both hailing from incredibly different backgrounds yet certainly finding common ground on one thing, class. They both live a life in which class is important. Class is a lost art nowadays and Key West was not immune. Chicagos has changed that. We encourage you to step inside and be transported back to something better than now...


  • Biscuit Miller Band
    Chicagos Signs the Biscuit Miller Band!! If you've ever heard this amazing group, then you know what a big...
  • Live Interactive Camera
    Owners Ben and Scott are all about giving their guests the best of the best that they offer. Whether...
  • Have a Cigar
    Come in here dear boy and have a cigar, you're gonna go far... That's right, if this Chicagos setup...

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Address:  610 Greene St, Key West, FL 33040

(305) 741-7891