Seasons Bar
Big Star
You won’t find another place in town where you can rub elbows with serious hipsters, listen to the likes of country crooner Johnny Paycheck and devour as many succulent, crazy-inexpensive tacos as you can. And when it comes to whiskey, the honky-tonk tavern Big Star has it down to a science. If the extensive list is overwhelming, just look to the chalkboard, where there’s a daily $3 shot, chosen from whiskey staples such as Old Heaven Hill and Four Roses. 1531 N. Damen Ave., 773-235-4039; bigstarchicago.com
Chicago Q
Feeling fancy? Head to the Gold Coast’s glamorous barbecue eatery for the Grand Bourbon Tasting. For $75, guests get nine one-ounce pours of hard-to-find bourbons and rye whiskeys. They’re served neat, accompanied by a rocks glass with a house-made ice cube and an eyedropper filled with distilled water. 1160 N. Dearborn St., 312-642-1160; chicagoqrestaurant.com
Delilah’s
The punk rock biker bar claims to have the largest bourbon selection in America—and we believe them. Most nights at Delilah’s you’ll find daily specials ($2–$3 Old Crow or Heaven Hill) and offbeat flicks, which pair together perfectly. How else are you supposed to get through two excruciating hours of Elvis: Aloha From Hawaii and Conquest of the Planet of the Apes? 2771 N. Lincoln Ave., 773-472-2771; delilahschicago.com
Seasons Bar
Favored by celebs and a mix of power-suit types, the tiny bar tucked away on the lobby level of the Four Seasons Hotel employs some of the most knowledgeable bartenders in town. The bourbon, Scotch and whiskey selections are just as prominent as those drinking them, with labels like Cragganmore 29 Year Old, Johnny Walker Blue Label, Pappy Van Winkle 23 Year Old and The Macallan 25 Years Old. 120 E. Delaware Pl., 312-280-8800; fourseasons.com/chicagofs
Lady Gregory’s
Though Lady Gregory’s maintains a casual vibe, this is not your average neighborhood watering hole. Wood-lined menu “books” list a world-class selection of more than 300 whiskeys, some hailing from as far as India and Japan. Sounds intimidating, but beverage director Kyle McHugh designed the program for novices as well as connoisseurs. You can sample any spirit on the menu in a taste, a one-ounce shot or a two-ounce rocks pour. 5260 N. Clark St., 773-271-5050; ladygregorys.com
Lillie’s Q
How do you celebrate your first year in business? Bucktown barbecue joint owner Charlie McKenna hooked up with Kentucky’s Heaven Hill Distilleries Inc. for a whiskey made and bottled exclusively for Lillie’s guests. In addition to that homegrown spirit, called Henry McKenna, you’ll find several other specimens of excellent small-batch sauce, including gems like Junior Johnson’s Midnight Moon moonshine, Death’s Door White whiskey, Koval Rye Chicago whiskey and WhipperSnapper Oregon Spirit whiskey. 1856 W. North Ave., 773-772-5500; lilliesq.com
Longman & Eagle
The Logan Square gastropub has picked up all sorts of accolades since opening almost two years ago—including a Michelin star—so it shouldn’t come as a surprise that the bar is a notch above the competition. You’ll find 38 whiskeys on offer daily for $3 a shot, plus flights of rye, single-barrel bourbon, white whiskey, singlemalt Scotch and rare selections. 2657 N. Kedzie Ave., 773-276-7110; longmanandeagle.com
The Matchbox
Don’t underestimate this spot just because it’s only 460 square feet. The Matchbox is known as a bartender’s bar, so you’ll likely spot a local mixologist or two savoring a drink. In addition to no-nonsense, handcrafted cocktails, it’s also known for an impressive lineup of whiskeys. 770 N. Milwaukee Ave., 312-666- 9292; thesilverpalmrestaurant.com/themachbox.php
