Found this little gem during one of my long walks in the city. Great selection of high quality cigars and s helpful staff all but guarantees that you'll have a good time. I tried a Davidoff for the 1st time at the suggestion of one of the guys and I liked it so much, I bought a 2nd to smoke on the patio. They have a BYOB policy so the patio is filled with people enjoying whiskey, bourbon, or their favorite wine with a good smoke. I'll definitely be back! read more

Up Down Cigar Shop - Tobacco Shops Near Me - Chicago, Illinois

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. read more

Up Down Cigar Shop - Tobacco Shops Near Me - Chicago, Illinois

I want to give this place 1 star so less of you come here but the fact of the matter is that this place is great: Good cigars, affordable, great staff, good conversation, you name it. read more

Where else in Chitown can you rub elbows with former NBA players (Dennis Rodman was here recently), actors (John Cusack is said to frequent this place), and down-to-earth locals in search of a nice tobacco buzz. My random trip to this place was one of the highlights from my weekend trip back to the ol' hometown. Prices were decent, fun atmosphere, nice helpful service. 5 stars. read more

These guys and girls are great! Up Down has been a staple in Old Town and smoking tradition for years. There is always a friendly face there to greet you and chat with while enjoying a "stick" from their vast cigar caves. I am still holing out hope that they make this a 5-Star place by investing in a smoking lounge that can hold more than the front of the store. Keep your fingers crossed! Main Line: If you are in Old Town, you need to stop, even if its only to look around read more

Great selection of cigars and accesories, and its located so temptingly in the middle of old town. The owner Diana Silvius presides over the most well known tobacco shop in Chicago. If you are going to smoke a cigar in chicago, and you can only go one place, this is it. read more

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I'm writing from total begginer standpoint; no expert on cigars here. That said, I smoke about once every week or two and this is my go to place. There is a great selection of cigars here. Oh, are you in the market for a pipe, or a nice lighter? They've got that here aplenty. I've never used this service, but I always overhear them speaking about the lighters they repair, so hey -- they've got that too. My favorite thing about this place, though, is coming in for a smoke. As much as I'm in favor of every place in my life not smelling like smoke, there is nothing like being able to light up a cigar, indoors, with a good buddy and a cup of hot chocolate (my prefernce if I'm not drinking). The Saturday night crew here is not to be missed. The Sunday morning crew are generally complaining about working about being hungover, but hey, who the heck isn't. read more

My husband and I went into this shop to look at the pipes and hookas. The employees there never said hello, offered help, or even looked up from their computer. Just because I'm not a rich looking older man does not mean that I would not have purchased something. Trust me, avoiding a customer in this place is VERY hard because its a small shop. I felt uncomfortable and ended up walking out after about ten minutes (being in sight of employees the entire time). I'm giving them two stars instead of one because they do have very good taste and the shop was really cool looking. They did have a selection of beautiful hookas but I will not support a place that does not have reasonable customer service. I don't expect to be ass-kissed, in fact I hate that, but what I hate even more is to be obviously ignored. read more

Love it, have for years. Great selection, knowledgable staff. Their prices are reasonable at the store or on their website. Up Down certainly should be in your circuit of cigar shops. By the way, one of the coolest spaces. You can even enjoy one while your there! read more

I'm no cigar aficionado but I do enjoy a cigar now and then... Up Down is great, the people are friendly and no matter your cigar skill level they are happy to help you...after a few visits they helped me find my new smoke of choice...Romeo Y Julieta Numero Dos ... read more

Awesome. For me , since the 80's when I had that route for Miller beer. I remember blocking Steve Stone's Porsche with my Barrel truck one time. Stonie was puffing away on a cigar leaning against his car when I came out.....very cool. read more

Small location, limited room to smoke on site. Difficult Old Town parking. Great cigar collection. Limited pipe selection. Very Helpful staff. Will be back again to try more of their selection. read more

Nestled in the street of old town, this cigar shop has been around for over 50 years, although the original owner has passed away, they still carry a great tradition of a great cigar shop with great selections and custom cigars from well known companies (Tatuaje, My Father, La Aurora, etc). They do open up the back patio during spring through fall but during winter, you are left with a bar stool around the cash register if you are smoking in the shop (Although I heard they will be opening up their upstairs for a lounge, it hasn't happened yet). Place is BYOB so pair your cigar with nice bourbon or scotch if you are not driving! read more

I love this place. They had the cigars I've been looking for and the employees were just amazing.

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. read more

when you add in the convenience factor of late hours(open til 11), free parking(in the lot next door), solid selection of AF products(opus anyone) and a staff that actually knows the difference between maduro and double maduro, then you can see why the prices are so much more than other well respected places like Iwan Reis or Jack Schwartz. so if you don't have the time to run into the loop(during office hours) or order online, its nice to know you don't have to settle for a SS from walgreens or gas station and can get a good smoke when you need it. for those shopping for others, there is a great selection of accessories, lighters, humidors and other knick knacks...and its still open until 11pm for those last minute gifts. just be prepared to pay for it. read more

As there seems to be to entries on Yelp for this shop I'm posting this under both. I've been smoking cigars for the better part of two decades now over three continents and 30 countries. Smoking their products and smoking their products on their soils. So of course now that I'm living in Chicago again I'm out to find a nice shop I can go sit at, read, and smoke a VSG (one of my favorites). I took a friend of mine here from out of town as my first visit. I'm not sure what the picture on this website is of the big pipe above the store because I never saw it. However, well done on the picture of Betsy from Mad Men; she could make smoking a turd look sexy! They certainly have a superior selection. My buddy found a few sticks he's been searching high and low for. Their lay out and décor is classy too. This is Chicago though so you're going to pay Chicago prices. Buying single sticks online would be cheaper, and that is even before Chicago taxes. Binnys is a great humidor with good prices if you're just looking to pick up some sticks quick. My only other dig is the seating. I appreciate a shop I can smoke in, especially since Illinois and Chicago decided to override civil liberty but the seating here is almost nil. There was room for about 4 people, max, to sit at non-backed bar stools at the counter. Not a place you can really sit back and read with a smoke. All in all I can't say I'll be back. Or at least I won't specifically head out that way, I'm not mad at them or anything. It's a classy shop and the staff was perfectly friendly but the prices aren't worth it if I can't hang out in a comfortable chair with a smoke. They also had a great selection of pipes and paraphernalia, but again, the prices were higher than other places readily available. Prost, Cheers, Salud, Bon Appetit, and all those great wishes! read more

Good place. Has good environment. In old town. In one of best neighborhoods. Plenty of cigars.

Great selection and cigars are in excellent condition. Super knowledgeable employees. Staff is really great wether you need no help or buying your first cigar. Free short term parking in lot, otherwise street parking. read more

Awesome Experience....My first visit and it couldn't have been Better !...Great selection of cigars and pipe tobacco...as well as any accessories you need...Scott was very knowledgeable and informative about the history of the place...great group of locals hanging out made it even better....oh, and their hours are awesome...open late!...This will definitely my go to place. read more

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. read more

Like most high end tobacco shops, you have to put up with obnoxious, cigar smoking frat boys of all ages, but this gorgeous store is worth it for the blending bar, one of the marvels of the city's smoking scene. Rather than smoking that Drum or Bali Shag, come over here and get educated on how to blend different sorts of fresh tobacco together for a taste that will hit you exactly the way you want, and spend about a quarter what you would on prepackaged smokes in the process. read more

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

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! read more

By far my favorite Cigar shop! I just got in to cigars and go here about 3-4 times a week. Great place to let loose and smoke a few! Great company, great folks. Prices are decent if you know what you're looking for. Great array of pipes, fairly expensive selection of Humidors, but definitely shows in quality. I have purchased many many things from UpDown and will continue to. Love it here. PLEASE GO! :) read more

I went in to buy a cigar for my cousin's husband for Christmas . I don't know anything about cigars at all and the young man in the front was very helpful and very nice and very happy about his job .if I smoked cigars I would definitely go all the time because the atmosphere was awesome and the customer service was amazing . I'm sure my cousin's husband will be very happy with his gift , read more

Up Down Cigar Shop - Tobacco Shops Near Me - Chicago, Illinois

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. read more

I've visited this place several times now and I still think it's one of the best tobacco shops around. As others have mentioned, the atmosphere is old fashioned and social. The staff is very knowledgeable on the items in stock and seem genuinely interested in their customers' satisfaction. I was particularly impressed with their diverse, yet meticulously picked selection of pipes and cigars. read more

Stopped in here after the Yelp event. Was looking for a new Zippo. They not only have every Zippo known to man, but any other kind of lighter, cigar cutter, cigarette case and anything else imaginable. The hand carved ivory pipes they had displayed looked like they belong in a museum. They also have the biggest selection of cigars I have ever seen in one store. The staff here was very nice, and all dressed in Santa suit jackets. I also noted the fact that they have a cigarette here named Black Death Filters. You gotta love that one. I did not make a purchase, due to the fact the prices are astronomically high. read more

They do have a great selection of cigars, fine cigarettes and smoking accessories. However, the prices are insane and not just because of the city tax. I paid more than $3 more for a pack of cigarettes (Nat Sherman Hint of Mint) than I do at Blue Havana. Granted I needed some as I was stumbling to another bar so they had me at convenience. read more

Awesome cigar bar! Great selection, Ecuador, Nicaragua, Monte Cristos, Ashtons, Great prices too! Can get pretty packed but everybody is really friendly, knowledgeable and courteous staff as well read more

Been coming here for a couple of years now, and I really like the people who work there and the selection of cigars/tobacco/pipes. The events there are nice as well. Perfect place to get a cigar if you are in Chicago. read more

One of the best classic cigar stores in the country, Great service and product selection. No fancy lounge with TVs... just a great place to hang with the staff. Plus, they host fantastic events with all the major manufacturers. read more

Nice shop with fair prices. Diana, the owner, has been in the game for quite a while and knows her stuff. She has her own cigars rolled exclusively for her in the Dominican. BYOB for a different night with some friends. read more

I never got into smoking in my life nor will I ever try that. But if I had visited this place ten years ago, things could be completely different now. For cigar or tobacco lovers this place must be wonderland. Extensive cigar selection and they can make stuff for you as you wish. Their pipes are works of art. I didn't see anyone tacky at all. They also have lighters and smoking accessories that are worth seeing. I got a lighter for an important person in my life and they offered gift wrapping for free. Really courteous staff. Recommend!! read more

I am an infrequent cigar smoker. I stopped in with my son for a celebratory cigar. Andrew assisted us. He was extremely knowledgeable, friendly, helpful, non patronising and guided Us in making a cigar choice that was a memorable. He gave us various options, various price points and is in my mind the perfect salesman. Do not be intimidated when you go into the store. Ask for Andrew. He'll make you feel right at home from the selection of the cigar, to the cutting of it, to the igniting of it. Unpretentious and friendly. Great experience. read more

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

Prices are a bit inflated but the smokes are superb, so no big deal.

Good place. Nice Peeps. Always helpful. Open Late. I also like their matches. Sure, tis a bit spendy but heck, I just really like the place.... read more

Went in a few weeks ago with two friends of mine who had never tried a cigar before, and the staff could not have been nicer. The guy behind the counter took my friends around, asked them what kind of flavors they preferred, and help make great choices for the both of them. Great selection, cool location. read more