Cigar World’s best cigar shops across the U.S. - Part IV

A few weeks ago, we started delving into Cigar World’s “best of” cigar shop list around the U.S. The first week, we covered west coast cigar shops. The second week, the best cigar shops in the northern states. And last week, we took a trip to the east coast to delve into the best cigar shops. 

This week, we’re excited to bring you the next part of our favorite cigar shops across the U.S. So, without further adieu, get our favorite places to buy cigars in the midwest states according to Google and Yelp’s reviews.

Best cigar shops in the midwest

If there’s one thing about the midwest that stands true, it’s their sensibility. They just want great things with no nonsense. They’ll tell you to keep the glitz and glam and just give them the good stuff. And this exact sentiment stands true in their cigar shops and places to buy cigars. So, if you’re traveling through Chicago or if you’re a St. Louis local looking for a place to hang your hat and get some great cigars, we’ve compiled the best cigar shops from Missouri to Indiana. 

Best cigar shop for the atmosphere:

Iwan Reiss & Co, CHI. If you’re traveling through Chicago or if you’re a Chicago local looking for a true cigar aficionado’s atmosphere, then Iwan Ries & Co. should be at the top of your cigar shop list. It’s one of Chicago’s oldest and most renowned cigar shops, and features a tremendous selection of incredible cigars from brands like Partagas, Cohiba, Hoyo De Monterrey, Macanudo, and many many more. One of the best draws for me personally is that they don’t serve alcohol. Instead, Iwan is a BYOB or BYOL (bring your own liquor) type of cigar shop, so you can feel free to bring a bottle of your favorite whisky, scotch, or carry some of your favorite beers in and enjoy a relaxing occasion with some incredible cigars and incredible people. If you’re looking for a luxurious setting to enjoy a smoke with some of Chicago’s finest cigar folk, don’t pass up Iwan Reiss & Co.

Best cigar shop for the deals:

Southside Cigar & Tobacco, Indianapolis.  Southside Cigar and Tobacco has been serving the Indianapolis Southside and Greenwood area with quality brand cigars, tobaccos and smoking accessories since 2001. Their mission is simple, provide a variety of cigars to satisfy the most discerning palate. And they certainly stand true to their motto of, “life’s too short to smoke bad cigars.” Their selection is outstanding, boasting some of the hottest cigars from Ashton, Emillio, Ezra Zion, Macanudo, Montecristo and many more. But, it wasn’t the selection of cigars or the atmosphere that singed Southside into my brain, it was their prices. Not only were they some of the lowest that I’ve ever come across in a cigar shop, the fine owners will also give you a 10% discount when you buy 10 cigars. So, if you’re ever in the Indy area, don’t miss out on Southside.

Best cigar shop for the drinks:

Brennans, STL. If you find yourself in St. Louis itching for a premium cigar and a beverage that’s going to really make a mark on your palette, please don’t skimp on Brennans. Now, one wouldn’t normally just call this place a cigar shop, it’s far more than that. It’s a neighborhood hangout, a cigar shop, and a craft cocktail lounge all blended into one special little spot. It’s a great example of a trendier, sexy cocktail bar and cigar shop doing everything right. The cocktails are fantastic, and the food is excellent, and the cigars are even better, and if that wasn’t enough, the service is beyond friendly. To be completely honest, out of all the cigar shops across the country that feature premium cocktails to elevate the cigars, Brennans may be doing it better (or at least as good) than anyone else in the U.S.

Best cigar shop for the selection:

La Cultura, KCMO. Established in 2018 and nestled in the heart of Kansas City’s Crossroads Arts District, La Cultura is a cigar shop that features a wide variety of premium cigars and a relaxing atmosphere to enjoy a fine smoke whether you’re in the company of great friends or total strangers. This is not your father's stodgy old cigar shop, as the chic, industrial layout provides patrons with pool tables and darts to accompany their cigars. While the atmosphere, the service, and great people set this place apart, it’s the selection that really takes it over the top. No matter if you’re a total cigar newbie or an absolute veteran, La Cultura is sure to have the premium hand rolled cigar that you’re looking for. If you’re ever in the KC area or if you’re a KC local looking for the end-all-be-all cigar shop in the area, don’t miss out on La Cultura.

Comment with your favorite cigar shop from the midwest!

We hope you enjoyed the list of our best cigar shops and the best places to buy cigars from in the midwest. There’s literally hundreds and hundreds of great cigar shops that we had to leave off the list (for now). So, if you’ve got a midwest cigar shop that you love, let us know in the comments!

Stay tuned next week for the best cigar shops or places to buy cigars in the south!

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  • Member Avatar
    (11 months ago)

    The Vineyard Market in Ozark MO.

  • Member Avatar
    (11 months ago)

    Best lounge in Kansas City is Outlaw Cigar and Brewery in North Kansas City, Missouri.

    Great atmosphere, cigars, and drinks. No other lounge like this in the KC area.

  • Member Avatar
    (11 months ago)

    In the Minneapolis area, Perfect Ash ( or in Hudson, WI there is Smokedale. Perfect Ash has a nice lounge and ambience. Smokedale has an enormous selection and great prices.

  • Member Avatar
    (11 months ago)

    Before covid I travelled quarterly to KC for business and visited La Cultura as it was easy walking distance of my hotel. Found it to be everything you say - instantly welcoming and comfortable, by knowledgable staff and friendy customers, even to a total stranger. I miss those folks.