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Home > What's New > I Love Chicago
I Love Chicago
Posted: Monday, June 06, 2005
By David Savona
A recent trip to Chicago left me longing for New York. Not the new New York, but the old New York.
By old, I'm not pining for five-cent Nathan's dogs, Checker cabs or the DiMaggio Yankees. (Not that any of those things sounds bad, mind you.) I mean old as in the days when I could smoke a cigar in a New York City bar or restaurant. The Giuliani New York rather than the Bloomberg New York.
My all-too-short trip to Chicago left me with the firm belief that the Windy City is one of America's best cigar towns, bar none. Let me give you a whirlwind tour just to give you a taste.
THE HOTEL
My trip to Chicago started at the hotel, the Hyatt Regency O'Hare. I landed with my boss, Cigar Aficionado editor and publisher Marvin R. Shanken, on the day of the Wine Tour, which was being hosted by Wine Spectator, our sister publication. The following night, at the same hotel, we were holding a Big Smoke.
After dropping our bags, we met in the hotel lobby and bought a cup of coffee, then took a seat by the entranceway. Out came the cigar case, and soon we were puffing on a pair of Arturo Fuente Hemingway Signatures. Can't do that in New York City.
By the time we were halfway done with our cigars, about half a dozen people in the cigar industry, plus European editor, James Suckling, had gathered at the table, turning this into quite the smoking meeting. No one in the lobby said a word about the smoke.
THE SHOPS

Diana Silvius-Gits at Up Down Tobacco.
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Chicago has superb cigar shops with expansive selections of cigars. I toured several the day of the Big Smoke, enjoying the long ride from the Hyatt into downtown Chicago in a cigar-friendly cab. (I believe the driver, a cigarette smoker, bent the rules on this one.) The first stop on my shop tour was Up Down Tobacco, owned by Diana Silvius-Gits, one of the nation's best cigar retailers. Diana's a hoot, and offered a shot of rum and a cigar to welcome me to Chicago when I walked in her store around 10 a.m. (Who could say no?) Her store, at 1550 North Wells Street in Chicago's Old Town neighborhood, is packed with cigars, including her own Diana brand, which is made by the Fuente family. It's decorated with her artistic eye. Every year, she holds a party that spills out into her back courtyard. (Diana is also a hero to Chicago cigar smokers, whether they know it or not. She's actively involved in lobbying to keep the city smoker-friendly.)
The second stop was Hubbard State Cigars, a smaller shop with a coffee bar and a few chairs inside and out, located at 6 West Hubbard Street, near the corner of North State Street and a few blocks from the Magnificent Mile. Rhoda Beghros handed me an espresso to go with my morning smoke. "We call it a Cuban breakfast," she said. Several people walked in while I was there, so it seems that her breakfast idea was quite popular.
After downing my coffee I hopped into another cab, this time one that was cigar-unfriendly (I held the burning cigar out the open window) for the short trip to 19 South Wabash Avenue. There, on the second floor, was Iwan Ries & Co., one of the oldest tobacconists in America. Iwan Reis, founded in 1857, is owned by the Levi family, and today, Chuck Levi is the proprietor. The store hasn't always been at this location, but the pair of well-aged, twin chandeliers makes it look as if it's been there forever.
This is a big shop. Hoyo Excaliburs, for example, have an entire case devoted to them. Cigars are everywhere. (The shop also has an amazing array of pipes, some of them quite ornate.) A small smoking room sits to the left, in the back, for customers to puff away on a recent purchase while watching the news.

The humidor at Jack Schwartz Importer.
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A short walk away was the last shop on my tour, Jack Schwartz Importer, a bright, stylish, well-stocked shop at 141 West Jackson Boulevard, in the lobby of Chicago's Board of Trade. The shop has a warm feel: it seems as if owner Billy O'Hara knows everyone who walks inside by name, and he and his staff quickly get everyone what he wants. (I saw O'Hara hand one customer what he calls a half-and-half, a box of cigars consisting of half of one size and half of another.) Customers can stock up and keep boxes in the walk-in humidor in the back, and there are several chairs and a rail for smoking. Not a bad place to spend an hour.
THE RESTAURANTS
After the Wine Tour, I hopped in a cab with Litto Gomez, who makes La Flor Dominicanas, and we headed to Café La Cave, a restaurant on the outskirts of Chicago, in Des Plaines. The maître d' met us at the door, and we asked for a table for two. "One where we can smoke," said Gomez. Without a pause, the man showed us to a table in the intriguingly gaudy cave room, a dark room made to look like an actual cave.
We lit up coronas before the meal. Café La Cave is one of those throwback restaurants, with classic dishes you no longer see on every menu: Steak Diane, Dover sole, the type of dishes requiring heavy tableside service. Escargot comes with the oversized tools used to grip shells made slippery with butter and oil. We ordered steaks, and had bigger cigars for dessert. No one blinked. "Glad to have you here," the maître d' said. It was as natural as you could imagine. "That's why I love Chicago," Gomez said. "They smoke here."
After my tour of Chicago's smoke shops, I went with Jack Schwartz's O'Hara to lunch at one of his favorite places, the Italian Village, and sat at the bar upstairs. Of course, we lit cigars. The place is a temple for devotees of red-sauce Italian. My marathon feast included linguine arrabiata, sausage, bruschetta loaded with garlic, and a plate of meatballs so tender, rich and delicious I wanted to cry. (Sorry, Mom.) We smoked cigars through the entire meal, and no one complained. (The bartender, a delightfully profane man, swore repeatedly about everything in the building except our cigars.)
Dinner my second night was with Suckling; we went to the Nine steak house with two of his friends after the Big Smoke. Nine is a hip eatery (there's another Nine in The Palms Casino Hotel Las Vegas), with a focus on great steaks and a truly lovely wine list.
After my hanger steak, we retired to the cigar-friendly bar and lounge and each lit up a well-aged Cuban. Mine was a La Gloria Cubana Medaille No. 2 with ten years of age. It was my last cigar of the trip and a blockbuster smoke. Not a bad way to end a whirlwind smoking tour of a great city.
For those of you living elsewhere, I heartily recommend a visit. And for you lucky souls in Chicago, I'm jealous. I hope you realize how good you have it and do everything you can to keep it that way.
Chicago Photo Courtesy of Photodisc/Getty Images Also in Cigar News:
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