Where Aroma Becomes Ritual

Cigars

Step into a humidor that feels less like a room and more like a sanctuary.

Here, rows of hand-rolled cigars rest in perfect condition, their rich aromas mingling in the air, waiting to be chosen and savored. The cigar experience at Havana High Rollers is designed for both the curious beginner and the seasoned aficionado. From the legendary Cuban Cohiba to rare limited editions from Nicaragua and the Dominican Republic, every selection carries a story of craft, tradition, and passion.

Lighting a cigar here is more than an indulgence — it’s a ritual. The soft crackle of the match, the first curl of smoke, the slow burn that invites you to pause and savor. Each draw carries depth, character, and the sense that time has stretched just for you.

This is where conversation lingers longer, where friendships are sealed in the haze, and where every cigar is more than tobacco — it’s a companion to the night. Whether you’re seeking guidance to find the perfect match or returning to a trusted favorite, our collection offers more than choice. It offers moments that stay with you.

Every visit is an invitation: to explore, to appreciate, and to discover how a simple ritual can transform an evening into something unforgettable.

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.

351 West Hubbard Street Chicago IL 60654 US
847.462.2196
5/5 based on 6 reviews

Stories From Our Guests

Guest Testimonials

Absolutely love the vibe here
Great cigars, strong drinks, and the slots keep things fun. A perfect place to unwind without any pressure.
Laid-back, grown-up, and
full of character
The staff knows their stuff, and the cocktail menu keeps surprising me every time I visit.
Absolutely love the vibe here
Great cigars, strong drinks, and the slots keep things fun. A perfect place to unwind without any pressure.

Join Havana Club

Get access to exclusive events, limited edition cigars, private tastings, and more.
Light a cigar. Raise your glass. Bet on yourself.