Over the last almost-decade, it has become increasingly more difficult to enjoy a cigar in the city of Chicago. With bans in bars, hotels, restaurants and virtually any other business that you could think of– cigar smokers were left to long walks on the beach and strolls through the park. Then the hammer came down on that as well. Chicago is nearly a smoke-free (and vapor free) city– inside and out.

Fortunately, if you are one that likes to sit back with a quality stick and perhaps strike up some conversation– there are still a handful of quality Chicago cigar bars that have not been extinguished.

These cigar bars are full of knowledge, with room to indulge in your new purchase (indoors).

Many allow BYOB and even food delivery. Your evening is about to become a lot more mellow.

Biggs Cigar Emporium

1150 North Dearborn Street, Chicago, IL 60610
(312) 809-2444

Biggs Cigar Emporium is one of the finest Chicago cigar bars when it comes to the atmosphere. Located in the historic Biggs Mansion– it is full of character, quality cigars and helpful people. They have two lounges, and private humidors that are available for rent.
Pop down in a chair, watch a game, strike up a conversation and indulge.

Casa De Montecristo

1332 West 55th Street, Countryside, IL 60525
(708) 352-6668

Casa De Montecristo is essentially the epitome of what some would envision to be a cigar bar. Rather than a few chairs to relax in– this is a full on lounge. What you would expect from a high-end restaurant. C-shaped seating areas line the walls, chairs and tables fill the middle, with a bar-top section to complete the atmosphere. The cigar selection is very impressive, with many hard to find sticks. The VIP-section is a must to check out. Seriously.

I understand that this is a little trek from downtown, but it is worth the venture.

Jack Schwartz Importer

141 West Jackson Boulevard, Chicago, IL 60604
(312) 782-7898

Jack Schwartz has not only been around for nearly 100 years, but they are also located in the heart of the business district. Wander over to the lobby of the Chicago Board of Trade after work, be guided through their phenomenal selection until you find the perfect stick, then pull up a chair in front of the large storefront window and watch the world pass by with every puff.

Iwan Ries & Co.

19 South Wabash Avenue, Chicago, IL 60603
(312) 372-1306

Iwan Ries & Co. combines the nostalgic feel of a speakeasy with modern conveniences to create an atmosphere that is hard to resist. There are two lounges available– a free one, and one that is for members, as well as patrons that have purchased a day pass. I recommend paying if you are planning to stay for awhile– once you see it, you will understand why.
Watch the traffic, play some chess– enjoy.

TESA Cigar Co.

1039 West Lake Street, Chicago, IL 60622
(312) 929-3075

TESA Cigar Co. just feels right when you walk in. The venue is very comfortable and it is very man-cave-esque. It pretty much feels like you are at your buddy’s hanging out for the fact that there is always intriguing conversation, it is BYOB and you can order food right to the door. Now that is a relaxing night out.

Up Down Cigar

1550 N Wells St, Chicago, IL 60610
(312) 337-8025

Up Down Cigar doesn’t just entertain your eyes with their well stocked selection of cigars, but also with the intricate decor that is all around. The smoking area does lack seating, so posting up at the counter or the meandering is required– however, there will be an outdoor patio come summer.


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