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Lighting Up: A good cigar can add a touch of class to your smoking regimen

By Daniel B. Honigman

On Jan. 1, Chicago’s new smoking ban officially snuffed out people’s ability to light up in bars and restaurants. And since this winter is already in full chill, standing outside your favorite spot to have a quick cigarette is, well, no fun.

But instead of freezing your ass off to enjoy a Camel Light, why not enjoy a nice cigar at home? “People don’t buy cigars because they’re must-buys,” says William O’Hara, owner of Jack Schwartz Importer (141 W. Jackson, 312/782-7898). “People buy cigars because smoking them makes the event much more memorable. You can be celebrating a party, a birth, a graduation—whatever. It’s an occasion.”

If you’re going to take the plunge and enjoy a handrolled cigar, there are a few things you should know first. When picking out a cigar, O’Hara suggests you give it a squeeze. “If the cigar is stored properly, you’ll find it has just a little bit of give,” he says. “You don’t want it to be too dry, because it won’t smoke properly, but you don’t want it to be too moist either. You’re looking for a smooth draw, because if you fight with the cigar, it won’t be as enjoyable.”

Because there are hundreds of cigar manufacturers in business, choosing the cigar that’s right for you is a very personal experience, says Raki Mehra, owner of Hubbard State Cigar Shop (6 W. Hubbard, 312/670-0687). But there are a couple of things you’ll want to consider: Cigars vary in length (they can range from four inches long to seven or more); thickness, which is measured in ring gauge (a cigar with a 64 ring gauge is one inch in diameter, and most cigars fall between 32 and 52); and, of course, flavor.

A cigar’s flavor has a lot to do with its wrapper (the tobacco leaf wrapped around the filler tobacco), and darker cigars will generally taste heavier and spicier than lighter cigars. “ The darker and [more] shiny a cigar looks, the more complex the flavors will usually be,” Mehra says.

Time is also a huge factor in picking out a cigar. A bigger cigar—a seven-inch Churchill, for example—can take up to two hours to finish, which is way too much time in the winter for most. A four-and-a-half-inch petit perfecto, on the other hand, takes as
little as 30 minutes. (Smaller cigars are also lighter on the wallet.)

Also, if you’re new to cigars, you probably don’t want to turn three shades of green. As much as you’re tempted, lay off that super-dark, Tony Soprano-esque double maduro cigar, no matter how cool you think it’ll make you look.

If you decide to become a full-time cigar smoker, you can’t just leave them laying around: Store them in a humidor, which runs anywhere from $20 to tens of thousands of dollars depending on how many cigars you want to store. You’ll also need a humidifier and a gauge.

The investment, says Mike Maddaloni, 40, a Loop-based web consultant, is worth it. “ When you’re smoking a cigar, you’re not running around or doing anything fast-paced, and it adds to a good experience,” he says. “I’ll smoke a cigar, and I’ll spend more money on that than people would on a pack of cigarettes, but in the long run, it’s cheaper.”

Quick cigar suggestions

The CAO America ($6-$8) is a beautiful-looking smoke. It’s not too full-bodied and has a bit of a chocolatey, earthy taste.

Since it’s cold outside, the Punch Champion ($3.50-$4.50) is a good short smoke.

For folks looking for a good budget cigar, the Occidental Reserve by Alec Bradley (roughly $2 on is a sure thing.

If you have $20 burning a hole in your pocket, you may want to check out the Graycliff Professionale. It’s worth every penny and is good for weddings, bar mitzvahs, graduations—or if you’re trying to kiss up to your boss.

This story originally appeared in the Jan. 8 issue of UR Chicago Magazine. You can pick it up from a UR Chicago box in downtown Chicago or you can read it here.