Cigar city dark woods free#
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. Seeing as this location doesn’t serve alcohol, it’s on a BYOB or BYOL (bring your own liquor) basis. They’re now in their 5th generation of management and ownership, and their knowledge around every brand and the blends behind them are second-to-none. They’ve proudly been serving the Chicago cigar community since 1857, and when we say their cigar expertise has been handed down from generation to generation, we mean it. Located just two blocks west of Millennium Park, this swanky downtown cigar bar features a tremendous selection of incredible cigars from brands like Partagas, Cohiba, Hoyo De Monterrey, Macanudo, and many many more. is one of Chicago’s oldest and most renowned cigar bars and lounges, leaving no question as to why it has made its way onto our top 5 list. If you’re interested in knowing more about Up Down Cigar Shop, visit their website here.
In addition to no entry fee, they’re also a BYOB establishment so feel free to bring any of your favorite libations that you wish to pair with your cigars. Unlike many of the other cigar bars in Chicago, Up Down doesn’t have an entry fee, which matches perfectly to their relaxed vibe. The warm and welcoming staff aren’t only knowledgeable about every cigar in the shop, but they’ll take the time to work with you and figure out your tastes so you end up finding the perfect cigar to suit your preferences. Located in the heart of Old Town, just a couple blocks off La Salle, this modest and comfy lounge showcases an extensive collection of cigars from top brands like Arturo Fuente, CAO, Padron, and Rocky Patel. If casual and unpretentious are two key aspects that you’re looking for in a cigar bar, then Up Down Cigar Shop is one of the best that Chicago has to offer. If you’re interested in knowing more about The Clayton, visit their website here. So, if you’re looking to break away from the dark woods and luxurious leather aesthetic of your stereotypical cigar bar, don’t waste another minute and get over to The Clayton. Unfortunately, if you’re looking to indulge in a cigar and a drink pairing, The Clayton doesn’t allow alcohol in their lounge, but you can bring any other kind of beverage you’d like. In addition to their selection, their knowledgeable and friendly staff have no problem catering to the tastes of anyone, from cigar beginner to cigar aficionado. Located just off Canal St., a few blocks southeast of Merchandise Mart, this cigar mecca is an incredibly easy location to access, and even more impressively, their tremendous cigar collection boasts offerings from many major brands. has to offer, which is actually what’s so refreshing about it. Looking for a sleek, modern, and hip establishment to enjoy a cigar or two in Downtown Chicago? Look no further than The Clayton.Īt first glance, this cigar hot-spot almost seems to borrow their aesthetic from an Apple store, and is without a doubt one of the more contemporary cigar settings that Chicago, or the whole U.S. If you’re interested in knowing more about Casa De Montecristo, check out the website here. It’s perfect for private events or corporate outings and is without a doubt one of the top VIP cigar locations that Chicago has to offer. In addition to the public lounge, if you’re looking for a show-stopping exclusive experience, the VIP room isn’t so much a room, but a cigar oasis. The public lounge space boasts a sea of lavish leather chairs, a multitude of TVs, and is perfect for enjoying a ball game or a unique night out.
With over 8,200 square feet of cigar retail space and lounge space, this cigar giant has several floors to choose from when looking for a place to kick back and enjoy a cigar. This relaxing and luxurious spot showcases a tremendous selection of premium cigars from brands such as Montecristo, Macanudo, Cohiba, and more. #5 Cigar Bar Chicago: Case De MontecristoĬasa De Montecristo Chicago is without a doubt one of Chicagoland’s premier cigar bars and cigar stores located in Countryside, just about 30 minutes west of downtown.
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