They always smoke outside on the sidewalk and the stinky smoke puffs into the faces of passerbys. Yuck!

Always a go to Cigar bar while visiting Chicago! The staff here always friendly, helpful and welcoming. I appreciate the covered outside area with patio heaters and big screen to watch sport's I'm not a cigar smoker, but we always find a stick for the husband to try and from my limited knowledge, they have a wide selection of great cigars. I also appreciate that you can BYO drinks . read more

Up Down Cigar Shop - As you enter, to the left. - Tobacco Shops Near Me - Chicago, Illinois

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I swing by here often when I want to sit and have a cigar. When the weather is turning cool, I like to find a place to relax inside. Up Down has a nice back patio with a big screen. There is no sound with the television but it's cool with me watching football without listening to the announcers. The staff is always helpful and always have recommendations for purchase. read more

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

Visiting Chicago for a conference. My fiancé needed to smoke a cigar away from the hotel. Up Down is located in a great neighborhood with several restaurants & bars. The staff is very welcoming. The one guy walked my fiancé around to show him shop & many cigars. There is a 1 cigar minimum which is great. It's usually a 2 cigar minimum at other places. The shop is eclectic with 5 bar stool counter seating. There is a high top seating for 2 in the window. They also have overflow seating in the back with a heated tent. Large selection of cigars and lighters. Would most definitely visit again even though I don't smoke. The ventilation is good. It's BYOB. read more

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

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Their selection of sticks was very good, and the prices were in line with the value served! I found my spot for cigars when I visit Chicago moving forward! The shop owner and the locals were all pleasant, and welcoming and they served free coffee! read more

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

Service was top notch- very knowledgeable bunch. Selection is the best in Chicago (period) and we would know as experienced cigar enthusiasts with over 20 years of experience. The value is excellent. Best compliment ever written is: I'll be back! read more

Highly recommend this place to purchase cigars or buy pipe tobacco. Friendly and knowledgeable staff and great outdoor seating area in the back. They even have a small coffee bar if you need a cup! I'll be back for sure. read more

Walked in; completely ignored. Looked at cigars for 10 minutes; ignored. All cases locked. No one asked if I needed help or suggestions. Maybe 2 workers. 4 'regulars'. Will not come back. Walked out and lit my own cigar in front of store. read more

Came here with a couple of friends to enjoy a few cigars. The staff was super friendly and knowledgeable. We enjoyed our My Father Connecticut cigars in the back tent area. The tent has heaters and tables to enjoy your smoke in the chilly weather. Will come back again. read more

I strongly recommend your next visit to Chicago. It is an excellent location and selection.

Great little spot in Old Town. They have a great selection of cigars plus a nice heated tent area to enjoy them. read more

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

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My favorite shop in the world, love everything from the staff to the regulars and the selection!

Truly horrible customer service. The gentleman with the shaggy bowl haircut seemed put off to have to help and clearly wasn't interested in answering questions. Go elsewhere. read more

Came the other day. They have a very nice selection of cigars. In pre Covid times there used to be able to smoke inside. They have a back patio with some heaters and seats. Some of the regulars brought their own booze to drink out back. Projector with sports. It was somewhat meh day weather wise with temps ranging from 40s to 50s with some condensation earlier and clouds. Little sunshine. I appreciated the tarp and the people changing the propane tank in the heaters. The regulars were cordial and friendly on back patio. read more

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

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This place has value to me. In the beginning in my journey cigars I was recommended this place. The professional service from the workers is top tier. The staff provided great service with amazing personalities. The selection is amazing, another spot with rich history. The regulars welcome you as apart to another family. Definitely great place to go to. Highly recommend read more

This is on of my husbands favorite cigar shops, located in old town. They have a great selection and the staff have a lot of knowledge. Service is great. read more

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

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Whether you smoke 1 cigar a year or 1 cigar a day, this venue is worth a visit. Andrew is the staff member that makes this experience so enriching. He looked up from what he was doing to greet us and politely inquired how he could assist us. Not obsequiously, he made me feel like royalty. I told him what I was looking for and my price range and he enthusiastically guided me through my options. He clearly enjoys a trusted position with the regulars; he is very knowledgeable about cigars. No upselling. No patronizing. He is the dignified concierge to this establishment. Thanks, Andrew. read more

Amazing place! I'm about couple hours away, and stop by every chance I get. Great staff, great selection, great atmosphere! These guys are my go to for good quality cigars! read more

This place is great for cigars because of its wide selection and amazing back door patio seating. Honestly the best cigar spot in town. Great for a little pit stop before going out and if you're in town for a short time they have everything you would want right at your fingertips. Can't recommend this place enough. read more

This is a very popular packed place. Extremely knowledgeable rep. Andrew suggested A.Fuente Maduro per my input of types of cigars I like. It's very reasonable priced but perfect for me. Also I appreciate hospitality and good care from the lady (Sorry I didn't ask the name!) read more

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

Can't say much more than what has already been said. Up Down Cigar is one of only a couple legitimate lounges, and one of only a handful of places you can find premium tobacco in the City of Chicago. The staff is amazing, the selection is second to none, and they put on great events on an almost monthly basis. I have been able to enjoy great events featuring Illusione, Rocky Patel, and My Father cigars! Definitely one of my favorite places in Chicago! read more

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Friendly accessible cigar shop. Up Down has a great selection of cigars. Prices are reasonable. It was nice to find a table to enjoy our cigars. In a city that is afraid to have cigar lounges...to a few cigar lounges that want "membership" to smoke their this Up Down was an oasis. Thanks for reading. Avram read more

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

It took me close to an hour to find a true cigar lounge on Google maps. Here's what you need to know in a nutshell: - Casual and welcoming cigar shop, open to all levels of smokers - Friendly, no-pressure management - NO entry "fee" like these other clowns - Handful of bar-style seats and table seating on OUTDOOR patio(!) - BYOB and BYO food - Neighborhood parking stinks but walk a darn block, ok? - In my opinion, fair-priced cigars (IL taxes are high, suck it up) read more

Good environment, and nice service. Workers were really patient and polite. Would recommend.

Super helpful staff, huge selection, and a great atmosphere for hanging out, smoking and sharing some drinks. Would definitely return. read more

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

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. read more

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 50th 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! read more

This is my favorite cigar lounge in the city. It's not the fanciest one, but it certainly offers the best value. There's a great selection of cigars; the staff is friendly and knowledgeable; and there are plenty of comfortable places to sit. It's also BYOB. Definitely check this place out if you're looking for a place to smoke a pipe or cigar. It's Old Town location is also ideal, as it's perfectly situated next to many restaurants and bars for a pre or post-dinner cigar. read more

6/21/18: Spent much of the day at Up Down and loved it! The staff was wonderful as usual; friendly, accommodating, and knowledgeable. It's a fine place to go and enjoy top-notch cigars and fellowship. I will return as often as I can. It's the best cigar shop in the city of Chicago! read more

Enjoyed this entire experience! Great customer service! Ambiance was good! Great location and knowledgeable & friendly staff

Great selection in a small comfortable shop. Weather permitting heated outside area. In a walking neighborhood with plenty of places to eat and drink without spending your cigar allowance. read more

Up Down Cigar Shop - Great Christmas gift. Hint! - Tobacco Shops Near Me - Chicago, Illinois

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Nice place to enjoy a stick. Stopped in there for my birthday smoke and my good pal Daniel got me a nice Arturo Fuente. Can't go wrong with that smoke always my favorite brand. Good conversation hanging out in the space with nice people. A great selection of cigars. Only downside is it gets a little smoky because it's small and my jacket stinks! To be expected when smoking sticks though. What can you do! Definitely will be back in when in Old Town. Thank you for the hospitality read more

This was my second visit & both times Andrew was was very helpful. Andrew presented good suggestions for the style of cigar I was seeking. Andrew was very knowledgeable about flavor, origin, how long of a smoke & price. Great selection, service & I look forward to my return visit. read more

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

I can only speak on my experience as a non-smoker attending a party in the beer garden out back. The staff was very friendly, the patrons were also super chill and the back area was a perfect place to host an event for a cigar lover. You can BYOB and food, you pay 20 at the door and that included a 15 voucher towards a purchase. My husband can't wait to go back. read more

Nice cigar selection. Small, but very hospitable staff. This was my first visit to Chicago. I looked for a nice place to enjoy a cigar. It's BYOB. I was in town for business. I will come back to this spot IF I ever make it back to Chicago. read more

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

I have visited the Up Down Cigar shop three or four times, and every visit has a different vibe. The employee's are quite helpful and the selection is good. There are always top notch cigars on sale at a decent price. I highly recommend the humidor on the side where they have their cut rate cigars. I have found some brand name cigars at a good price in there. It has something for everyone. If you need a gift for a cigar or pipe smoker, it's a must that you visit this place. read more

You'd think being an early twenties woman walking into a swanky little cigar shop on Wells in Old Town would be an uncomfortable experience. But see, you'd be thinking wrong. For the last few years, I've come to Old Town to look for all my boyfriend's cigar fixes and in the interm, have learned a lot about cigars, the accoutrements, and even found myself dabbling in swanky cigarettes and cigarillos. With its small and open floorplan, with cigars in see-through cases that line the walls, its like walking into a library of cigars, which would be wholy approporiate since the selection is encyclopedic. The staff are SO courteous, helpful, engaging and knowledgeable. Think of them as librarians who don't shush you for talking. Tell one of those cigar librarians you need help, and they follow you around and make recommendation based on some random questions they ask. There will be some hits or misses (as they're not mind readers) but they always make you feel like Ms. Moneybags, even if you're not spending the big bucks. read more

I've been smoking cigars for about two years now, and I really began my cigar education at UpDown. Walking in made me feel like a little kid walking into the Lego Store many years ago. Aside from a great atmosphere and a varied selection, the only iffy thing about UpDown is the lack of seating and the inconsistent staff service. I've walked in and someone has helped me right away, but I've spent 15 minutes waiting for a worker to help me out and open up a case. If you're there with a friend, it can be an interesting time delving into the world of cigars, but it can be disappointing if you purchase some cigars to have right there and then and you're forced to stand up and have your cigar. I don't need a La-Z-Boy chair, but space is definitely a concern at UpDown. Aside from technical aspects, the cigars there are kept in good condition, and you can get a great cigar at a reasonable price. Go for anything in the full-flavor corner (the corner with the Tatuaje, Padron, Alec Bradley, and O.S.O.K. cigars). The O.S.O.K. room 101 is a personal favorite. The buzz puts you on your ass, but you barely notice because of the comfortable draw and the consistency of spice and strength. Stop by and see what UpDown has for you. read more

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. read more