Up Down Cigar Shop

Stumbled onto this by luck. The service was excellent, the tall guy with the glasses knows his cigars very well, the selection is a 9. If they had a few more stools it would be a 10. Perfect location. Will be back!

I have been coming here for years, since I used to live in Chicago just a few blocks away. I visited again while in town, and I felt it’s time for a review.
It’s a nice size shop, with lots of glass displays, and well stocked. The «counter» is a circular area in the middle of the shop, where customers conduct the business of paying for their purchases, or sit at high stool to light up their cigars, and engage in conversation.
The staff is always helpful, and in more than one occasions steered me or my companion in a good direction with selections. This time I asked for a specific cigar, and the gentleman behind the counter — who had attentively approached me to ask if he could help with anything — checked on their computer system and they did not, but they had similar cigars from the same producer, and I made my purchase.
When needing a cigar in Old Town, or Lincoln Park, go here.

A wonderful experience shopping for the perfect gift! Very patient and helpful… A definite add for any aficionado

A beautiful store on a charming stretch, Up Down Cigar was the second stop on my semi-​intentional survey of Chicago cigar shops. I’m not sure any place in Chicago can rival Iwan Ries & Co. for sheer selection, but Up Down seemed well-​curated and staffed by the patient and knowledgeable Riley, who not only made reasonable recommendations to me but also kindly answered my greenhorn questions about cigars. I haven’t had a chance to check out their smoking patio yet, but I look forward to returning and learning more.

Awful service look at you like you can’t afford a thing. You buy a $ 13 stick and no thank you

Great cigar selection. They get rare cigars most shops can not get. Wish they had a smoking lounge but ill take what i can get.

Amazing selection and an actual private garden in back to enjoy your picks. This place is recommended by tobacconists.

Had good service to find a nice, light cigar. Went with the suggested Dominican ($ 9), which was good and light! Staff and service were great!

Great selection. Hip, upscale, modern shop. Friendly service. Pricey, but open super late.

This is a really cool store. The guys who work here are friendly and knowledgable and they keep a record of what cigars you like. I buy pipes for my dad from here for every holiday and he always loves them.

Came here with a friend who is a regular customer. Up Down is an awesome place with an endless selection. The cigars selection is top notch and the employees know their cigars. The back patio is a nice touch if you want to smoke on a nice day. It’s a friendly place and I’ll be returning when I’m in the area.

Stopped in here after dinner while on a recent business trip to Chicago.
Great selection and had a great time talking with the gentleman behind the desk as I enjoyed my cigar.
A lot of great history about the business and its owner, so definitely take the time to talk shop with the employees about both.
Going to be a regular stop for me when in Chicago from now on.

Looking for a good smoke in Old Town? Look no further, welcome to Up Down Cigar Shop!
Selection wise this shop carries most major brands cigars and a large variety of pipes and pipe tobacco. Walking into their showroom you’ll see Ashton, My Father, Altadis which includes Montecristo, Dominican Cohiba, Opus X, Arturo Fuente, Liga Privada, Palina, Padron, and of course Tatuaje.
As a brick and mortar the shop carries a solid selection and has many store exclusives produced by Jaime Garcia, Davidoff and Tatuaje to commemorate the shop’s 50^th anniversary. I was able to have them dig through the back room and find me some vintage God of Fire 2004 and I was happy to buy them all. Overall the staff is helpful and knowledge as well as hospital.
I found their recommendations to be thoughtful and they were definitely down to shoot the breeze and talk tobacco. It’s a great business however its smoking area definitely needs much work. You won’t find big comfy leather couches in the shop and will have to settle smoking at the counter or one small room in the front. They’ve recently opened a beer garden for the summer where you can go in the outdoor patio.
Updown Lounge is a great venue and hosts many cigar events with some of the biggest names in the cigar industry. It is a Chicago foundation but be prepared to pay your 30% cigar tax!

Very friendly service. Patient and knowledgeable. Even gift wrapped a present for me!

Been coming in here for a few years now and continue to love it. Staff is friendly and knowledgeable. I tend to be picky with the style/​type of cigars and the staff have offered great recommendations. Ive also bought a quality humidor here and happy with the purchase.

Been going to this place for nearly a year, as it’s about the only place I’m aware of on the North Side where you can actually smoke a cigar inside. Great selection of products and in the last few months they’ve done the wise thing and added a flat screen making it a great place to relax and watch a ballgame.
The clientele are mainly professional people from several walks of life. Chicago police regularly stop in to buy cigars and the conversation is frequently free flowing and enjoyable. Sports, politics, etc. I’ve even had my picture taken with Jimmy Jackson (ex-​NBAer) and Al Sharpton (of Tawana Brawley fame). Phil the owner is a solid guy and a big Blackhawks fan who remembers his customers’ names and makes you feel welcome.
My only gripes here — and I noticed this has been mentioned by other reviewers, so I’m apparently not crazy — is that there is an «inner circle» feel re: the people who work there. They treat the regulars — and each other — with a high degree of familiarity and friendliness, but for those who were only semi-​regulars (like me), there’s a decidedly cooler feel. There are often 2 – 3 of them on duty clustered behind the counter, smoking, chatting and laughing among themselves. I don’t mean to over play this, and I never had a hint of an issue with any of them. But they could use some training I believe on making everyone feel welcome.
The other gripe is that they shouldn’t let people smoke cigarettes inside. One of the employees regularly smokes cigarettes, and occasionally a customer will as well. Cigarette smoke is infinitely more irritating to eyes, nose and palate, unlike cigar smoke which is fine, especially in a cigar shop. I wish they’d put an end to this.

Upscale tobacco shop with a very knowledgeable staff. Definitely not to be confused with other smoke shops that cater primarily to hippies. You won’t find vaporizers or cigarettes, however, you will find quality cigars and accessories. They have a great selection of loose tobacco. Impressed with extensive inventory of Porsche products. They have both, classical and modern, smoking accessories. Definitely worthy of a stop if you are a tobacco connoisseur.

Best selection of cigars in the city, that I know. Staff is very helpful, and the location lets you enjoy the neighborhood after you leave. No TV’s, but I like that you can come and focus on the conversation with people. They throw monthly events in the spring/​summer months that are pretty fun too. The seating is kinda tough sometimes, especially when it’s a lot of people.
All in all a pretty fun place.

Cigars are both noble cultural traditions and symbols of brutish white male culture.
The staff where cigars are procured are barometers, to which culture the establishment caters to. Wether it’s TESA Cigars which sullies to the lowest guttural denominator or to Burning Leaf Tobacco and Blue Havana, exemplars of the noble tradition that I partake once or twice monthly, while striving to keep my humidor at plum producing levels on the aged and oily cigars I favor, especially the La Flor Dominicana Double Ligero Maduro, (LD).
Burning Leaf only sells the LD as a smaller corona. Because I only smoke once or twice a month, I prefer the double Corona, which Blue Havana sells. But they’re located too far from Logan Square for winter trips.
Last week I was in Old Town for a Chicago Teacher’s Union Fundraiser. It was near a Starbucks so I grabbed a pound of fragrant yet bold French Expresso, which is a grand accompaniment to a strong cigar and was the start of Fidel Castro’s day before he gave up cigars.
Then I ventured into Up Down and as Fortuna had it, the first thing I saw was the LD double croronas! I reached for a few and discovered the cabinet locked. Generally most shops keep their cabinet’s open as a statement of trust to the customer.
I turned and there stood an old rag weed with a ZZ Top beard going for a Willie Nelson look.
” We keep our cases, looked”, said he, actuating the word «locked» with hostility.
As if I was behind the need for the locked cases and he was sending a message to the rest of my pick-​pock and shelf/​counter swiping crew that I lead as the Black Fagin updated from Oliver Twist. And instead of living in an «abandoned house on a stranded street by a marketplace» like Fagin and his crew, my crew squats in the Cabrini Green Housing Project, (formally down the street from them), now closed by Chicago’s Transformation ²⁰⁄₂₀ Plan that ethnically cleansed the neighborhood, creating the gun violence on the south and westside.
I wasn’t surprised. I’ve seen relics like this before. He pictures himself as some wizened and organically erudite box car scholar, worthy of a place under the Henley Street bridge in Cormac McCarthy’s novel Suttree.
The reality is he’s a throw back to an era when the «old rugged white man» were iconic of American strength, grit, and determination, that extended American armies across seas in wars of John Wayne masculinity, while promoting hollowed American Optimism and parochialism here. The same «white men» who made politicians like Nixon and Reagan.
Clearly he is the southern sheriff of Up Down.
But out of civility and as a student of cigar culture. I let it slide and expressed my pleasure. Not just about securing cigars I’ve been hoping for since fall, (they will have to be aged to get their maximum potential) but also not having to hunt for them because I always forget their name, as I was running late as usual. So while I’m making small talk about how great the LD’s are and how this was the first place I was able to find the proper size, he just stairs at me. I’m sure picturing me selling stolen cigars on the blue line train.
«Do you want one cigar» as if I’m not truly interested in buying.
No I say and select three. I’m still upbeat because they’re moderately priced excluding the various heavy taxes, which should only be levied on cigarettes because they do far more damage to our fragile healthcare system. Then I ask if he freezes his cigars before transforming them to his personal humidor? It’s an ongoing debate due to the scourge of any humidor, tobacco beetles. I still have nightmares about them after they came this close (-) to destroying my aging Cubans. He replies «no». Leaving me to wonder if he understood what I was talking about. So I rephrased explaining it in context” And again he just said «No»
At this point I’m getting pissed and I’m about to say something. When a fellow steps in and gives me a lengthy scholarly lecture on beetle infestation. All of which I know from reading several cyber sights, some of dubious nautre So it’s still good to hear it from a professional,
who really knows his cigars, which even in the better shops, is still rare.
Those who sale cigars should not just be both informational steward and Cigar «physicians» It’s because of this fellow that I didn’t feel the urge to freeze these newest additions now aging in my humidor. I just wish I had encountered him because the two starts would have been three starts. But because of him, it’s not a one star review.
Indeed this gentlemen’s intervention and his knowledge of those wretched beetles and their cursed breeding habits and conditions, reminded me of those rare cigar masters at The Tobacco Exchange Located off some twists and turns of what was Pirate’s Alley were many a sad case found themselves waylaid and set upon before ending up as fair to some savage crime bygones ago in the french Quarter of New Orleans

I was pretty underwhelmed by this place. Its good selection and convenient hours are definite pluses. But, the rest was a poor experience.
I walked in on a Friday night and there were several groups of people standing around having conversations. As none of them were behind the counter, I couldn’t figure out who worked there. I started looking around and found what I was after fairly quickly. So, I just stood there and tried making eye contact with anyone, to no avail. Finally a different customer broke off to buy something and I was able to pin down a guy to get my smokes.
Come on guys. If you have all of your stuff behind locked glass and a customer is just standing there with his arms crossed looking hopeful, at least take a cue and help him out.
I purchased three smokes and asked if they sell any bottled water. Nope. Literally every single person in the store had an «Up Down Cigar Shop» coffee mug in front of them, so I was hoping maybe I’d be directed to wherever these are obtained. Nope.
So, I just sat down at the counter and lit up one of my cigars. I started to get a sense of who was an employee since a few of the guys would periodically walk behind the counter, but none of them even made eye contact with me. I tried striking up a conversation with one guy by mentioning I was from Phoenix and that his shop had been recommended to me, but that elicited an «Oh.» before he went back to his more important customers.
It’s unfortunate that it really is possible to sustain a cigar shop on a small circle of regulars who buy lots of cigars, because owners get complacent about reaching out and being friendly to new customers. Too bad, guys. You lost out on my repeat business while I was in town, and back in Phoenix I’ll definitely be telling people NOT to go to your shop when they travel to Chicago.