Absolutely love the vibe here
Great cigars, strong drinks, and the slots keep things fun. A perfect place to unwind without any pressure. 
Mike Cary IL
Sit back. Light up. Feel the calm.
Havana
High Rollers
A space where cigars, cocktails, and games blend into an atmosphere of refined relaxation.
Light Up. Press Play. Pour Slow.
Not Just a Lounge
Your Kind of Escape
At Havana High Rollers, the scent of hand-rolled cigars drifts through the air, slot machines hum with possibility, and the bar serves pours as smooth as the atmosphere.
This is where smoky nights, bold flavors, and a bit of luck come together. Whether you’re here to kick back with a drink, spin the reels, or light up and linger — every visit is a break from the ordinary.
Our Signature Experience
Our Specialties
Join the Havana High Rollers Club
Get access to exclusive events, limited edition cigars, private tastings, and more.
Become more than a guest — be part of the club.
Where Smoke, Spirits & Spin Come Together
The Lounge That
Plays Your Way
Grab a drink, light a cigar, and try your luck — all in one laid-back space. With vintage slot machines humming beside deep leather chairs, Havana High Rollers blends casual fun with grown-up comfort.
Whether you’re here to unwind, socialize, or chase a lucky streak, the lounge is always in play.
Where Aroma Meets Ritual
The Humidor – Our Cigars
Personal
Recommendations
We help you find the perfect cigar — from beginner to aficionado.
World-Class
Brands
Cohiba, Arturo Fuente, and rare limited editions from around the world.
Preserved
in Perfection
Expert humidors ensure every cigar is fresh and aromatic.
Raise Your Glass
Cocktails
& Spirits
From slow-sipped bourbon to bold tropical blends, our bar serves up more than just drinks — it sets the mood.
Whether you’re craving an Old Fashioned, a splash of fine rum, or one of our signature creations, there’s always something smooth waiting behind the bar.
351 West Hubbard Street
Chicago
IL
60654
US
847.462.2196
5/5 based on 6 reviews
Stories From Our Guests
Guest Testimonials
Laid-back, grown-up, and
full of character
The staff knows their stuff, and the cocktail menu keeps surprising me every time I visit. full of character
Bob Crystal Lake, IL
Absolutely love the vibe here
Great cigars, strong drinks, and the slots keep things fun. A perfect place to unwind without any pressure. 
Mike P. Naperville, IL
Join Havana Club
Get access to exclusive events, limited edition cigars, private tastings, and more.
Light a cigar. Raise your glass. Bet on yourself.