Trying to Smoke, Chicago

Our associate editor visits the Windy City in search of cigar-friendly places.

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I'm going to spare you the usual Sinatra references to Chicago and get right down to it—Chicago is not the town I left. It has been six years since I last had the pleasure of freezing my tail off on wind-raked Michigan Avenue. The only difference was, six years ago, one could come in from the cold and light up a cigar at pretty much any steak house, bar or hotel lounge. If you didn't have a pocketful of your own smokes, not a problem—every place had a humidor. That was six years ago. Since then, a smoking ban has wiped the city almost completely clean of any indoor smoking. Forget cigar bars, for there are none. All the indoor smoking is done primarily in shops, most of which were never meant to accommodate lounging patrons.

On my brief stay in Chi-Town, I had one afternoon to assess the smoking situation. I started by returning to one of my old standby cigar shops on Hubbard Street. I used to buy cigars there when I'd stay at the Renaissance Hotel on Wacker Drive. The scene was heartbreaking. Not that there was anything wrong with the shop: it still had all its charm and plenty of inventory, but I was told that I was not allowed to smoke inside. The landlord recently changed the conditions of the lease, which makes no sense. It is a cigar shop. People smoke cigars in a cigar shop. That is how the shop pays the rent. So I ended up talking about cigars in the little store instead of smoking them, because talking about cigars is all you're allowed to do. That and drink coffee and read a magazine about cigars. What sadness. I bought a Fuente Hemingway Work of Art Maduro and was on my way. Had the weather not been so cold and windy, strolling the downtown area with a lit cigar would've been delightful. Not an option.

I thought I could walk to the financial district from Hubbard, but that lake-effect winter wind just menaces the downtown area and took the fight right out of me. A quick cab ride later and I was dropped off between two stone statues on a promenade leading to the Chicago Board of Trade building on West Jackson Boulevard, a bustling art deco structure that houses tobacconist Jack Schwartz Importer. It's a small shop with a few highly coveted chairs and some standing room usually overtaken by the handful of patrons wishing to stick around. It is a handsome shop as well, very becoming of its financial clientele. Like the stock market, Jack Schwartz closes at five and is not open on weekends. Even though I had the Hemingway in my pocket, I bought a Padrón 1926 No. 35. The 35s looked like a good batch of naturals and I didn't want to smoke something purchased elsewhere.

"So where does someone go to smoke after work hours?" I asked.

"They don't. This is pretty much it," answered Eric, one of the store managers. I finished the Padrón and made my way to Ohio Street where I stopped in at a Lavazza cafe. I had never seen one before and didn't know that the famous espresso company had opened branded shops. It's a great little place that pulled near perfect shots of espresso, a pleasant way to cap off my Padrón and warm me up before getting back to the streets.

My time was limited, so unfortunately I was unable to do a comprehensive tour of Chi-town's cigar shops, but one visit to mainstay tobacconist Iwan Ries turned up a surprise: a large lounge. The store is located in one of Chicago's landmark buildings on Wabash Street alongside the elevated train trestle. The 1,000-square-foot lounge is on the second floor and offers large windows, a cool view of the train and lots of natural light.

The member's lounge of Iwan Ries.

Kevin Levi, who owns the shop with his father, Chuck, made sure that some of the architectural elements were preserved, such as the gorgeous giant window frames and the original sculpted, decorative steel columns that nicely allude to old Chicago. Intermittent rumblings of the passing trains remind you that you are in fact in downtown Chicago and add a unique touch to the black leather chairs, televisions and wood floors you find in so many cigar lounges. Everything there is strictly BYO, and there are no humidified lockers or spirits. Nonmembers pay a $10 per diem fee, and the lounge closes at 5 p.m.

Luckily for me, Kevin let me loiter in the lounge until 5:30, which was enough time to finish the cigar he gave me—a Hoffman House Lonsdale. Hoffman House is a defunct vintage brand that Iwan Ries resurrected from obscurity by contracting Altadis U.S.A. to make in the Dominican Republic. The shop pays homage to the history of the brand with displays of some of the original gold-bronzed lithography and a full box of old perfectos that looked as though they came right out of Al Capone's humidor. I gave Kevin a Cuban Cuaba 2008 Edición Limitada in return. Fair trade, I believe.

It's sad that the shop closes so early, but really even sadder that cigar smoking and nightlife in Chicago have been forced apart by local legislation. Remember, the illustrious Club Macanudo had a location on East Walton Street before its demise. So it goes. But I believe that Chicago will be back one day and you'll see more cigar bars inhabiting the spaces of the city's beautiful architecture. Although this might not be any time soon.

The next day I went to lunch at NoMI, a beautiful airy restaurant on the seventh floor of the Park Hyatt on Michigan Avenue designed with mosaic floors, etched steel panels, Venetian blown glass fixtures and a marble wine-tasting room. After lunch on my way out, I noticed a pair of glass doors near the entrance that opened up to a wonderfully spacious terrace and stunning city view. It was snowing, but I could imagine some pretty swanky cigar parties out there in warmer weather.

"Excuse me," I asked the hostess. "Do you allow smoking out on the terrace during the summer?"

"Oh no," she replied. "That would expose our employees to secondhand smoke, and we wouldn't want to do that."

Of course not.

Adam Sarrazine October 3, 2010 2:21pm ET
Its not in downtown Chicago, but if you're in the Northwest Suburbs, Habana Cigar House (on 25/Algonquin Road) is a great place to spend an afternoon watching golf, playing cards, and (of course) smoking cigars. The staff is great; meeting regulars by name, and knowing their cigar preferences. The lounge area has comfortable seating, adequate ventilation, and enough space that you can hold a conversation without speaking over another group.
Amy Reid Champaign, IL, US, December 8, 2010 5:56pm ET
There's a great place a couple hours south of Chicago in Champaign, IL that's a GREAT cigar hangout called Bacca Cigar ( The owner is super friendly and knowledgeable and the atmosphere is comfortable. Their walk-in humidor is really cool too.
Chris Schedel Chicago, Illinois, US, December 14, 2010 10:18pm ET
Blue Havana at Belmont and Clark is a great place to buy and smoke cigars after work. They have a huge selection of cigars and provide a very comfortable environment in which to smoke.
Sam Sullivan December 28, 2010 2:25am ET
One of my favorite spots in Chicago is Up Down Cigar, in Old Town. They have an incredible selection of cigars alongside beautiful pipes and other tobacco miscellany. Most importantly, they have a cigar bar (albeit a small one) open late, a feature great in a city where that isn't all too common.
Vern Sheldon Portage, IN, USA, February 10, 2011 2:52am ET
In the Indiana burbs, Karma Cigars in Merrilville is a great place to relax and have a liesurely smoke. Freindly, knowledgeable staff and comfortable seating, and the best selection in Northwest Indiana.
James White Chicago, IL, USA, October 24, 2011 3:34pm ET
There isn't but one thing I hate about this wonderful city of Chicago that I live in: YES! you guessed it: This stupid smoking ban
James Richardson March 24, 2013 5:40pm ET
Jack Binion's Steakhouse at the Horseshoe Casino. Two bars on the casino floor as well. Free shuttles from Chicago. Cigar smoking permitted throughout.
Sam Zimmerman Arlington Heights, Illinois, United States, August 19, 2013 11:47pm ET
Neumanns Cigars & More in the Long Grove and Libertyville are really great places.
Peter Hook March 23, 2014 8:46am ET
I had a very enjoyable time at Tesa cigars at 1039 W. Lake St. Open late, great laid back atmosphere. BYO. Very highly recommended.

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