Cigar Bar Chicago: Top 5 In the Windy City

If you’re looking for the best cigar bar in Chicago, there’s no doubt you’ve come to the right place. No matter if you’re traveling through Chi-town on vacation, for work, or if you’re a windy city local that’s looking to kick back with a cigar and a drink, we’ve compiled the best places to light up and enjoy the finer things in life.

So, don’t waste another minute, grab your favorite stogies, a few pals, maybe some co-workers, and take in everything that the Chicago cigar scene has to offer.

#5 Cigar Bar Chicago: Case De Montecristo

Casa 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.

This relaxing and luxurious spot showcases a tremendous selection of premium cigars from brands such as Montecristo, Macanudo, Cohiba, and more. 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.

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. 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. 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. 

If you’re interested in knowing more about Casa De Montecristo, check out the website here.

#4 Cigar Bar Chicago: The Clayton

Looking for a sleek, modern, and hip establishment to enjoy a cigar or two in Downtown Chicago? Look no further than The Clayton. 

At 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. has to offer, which is actually what’s so refreshing about it. 

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. 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. 

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. 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.

If you’re interested in knowing more about The Clayton, visit their website here.

#3 Cigar Bar Chicago: Up Down Cigar Shop

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. 

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. 

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.

Unlike many of the other cigar bars in Chicago, Up Down doesn’t have an entry fee, which matches perfectly to their relaxed vibe. 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.

If you’re interested in knowing more about Up Down Cigar Shop, visit their website here.

#2 Cigar Bar Chicago: Iwan Ries & Co.

Iwan Ries & Co. 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. 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.

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. 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.

Seeing as this location doesn’t serve alcohol, it’s on a BYOB or BYOL (bring your own liquor) basis. 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. Nice little pro tip, Iwan & Co. will happily supply you or your party with glasses and ice.

The luxurious and almost coma-inducing lounges seem to provide more relaxation than most people’s homes, so if you prefer peace and quiet, you won’t have a hard time finding a little nook to call your own. But, if you’re in the mood for a little conversation and comradery with Chicago’s finest cigar folk, the public spaces also offer a lively scene. This is Chicago, is it not?

Do keep in mind, there is a $15 dollar entry fee for a one-time visit, or if you’re interested in making Iwan & Co. a regular location, they also provide memberships. 

If you’re interested in knowing more about Iwan & Co. visit their website here.

#1 Cigar Bar Chicago: Biggs Mansion

When trying to decide on the best Cigar bar in Chicago, we had a really tough time. There’s just so much competition. But, after much deliberation, we had to give it up for Biggs Mansion. 

This cigar lounge, located directly south of Old Town one block off Division is nothing short of exquisite. So much so, it’s been featured in Jerry Seinfield’s Comedians In Cars Getting Coffee, and it has had the prestigious honor of hosting the Cigar Smoking World Championship.

If you’re looking for a classy establishment that’s sure to give you a taste of the good life, Biggs is just for you. 

They offer a few different options for shopping and smoking. If you’re in town for a few days or if you’re a Chicago local that’s looking for a non-membership option for a cigar lounge, you can easily purchase a day pass for $85 dollars. You’ll have full access to the entire space, and you’ll be able to bring your own beer or liquor if you’re looking to pair your cigar with a beverage. However, do keep in mind that there’s no cans allowed and if you’re bringing a bottle it has to be 750ml or smaller.

If you’re not into a day-pass kind of commitment, you’re free to hang out in their awesomely stylish public lounge with the purchase of any cigar. Unfortunately though, with the public lounge there is no BYOB program available, so if you’re looking to enjoy a drink with your cigar, you may want to go for the day-pass option.

If you’re interested in knowing more about Biggs Mansion, check out their website here.

Enjoy the Best Cigar Bars in Chicago

From all of us at Cigar World, we hope you found this article helpful in your search for finding the perfect cigar bar in Chicago. So, next time you get a bit of “me time,” get out there and enjoy a night out on the town with your favorite people and your favorite cigars. 

If there are any of your favorites that we left off the list, we’d love to hear about them in the comments.