It's been a while since you made the faux pas of referring to Jack Daniel's as a bourbon, and you have a half-dozen of those Blanton's Kentucky Derby corks stored on a windowsill somewhere...so where do you go when you want to truly appreciate the best thing to ever come out of Kentucky? Aside from a road trip to the birthplace of Abraham Lincoln (okay, maybe he's the best thing to come out of Kentucky), there are a few spots around town that can satisfy your thirst for that sweet, brown goodness we all know and love.
Find Selection, selection, selection at Delilah's
Delilah's owner Mike Miller is to whiskey what Hemingway claimed to be to bullfighting—an aficionado. He not only runs the bar with hands-down the biggest selection of whiskeys in the city (he advertises more than 300, and the specialty is, yep, bourbon), but has written scholarly articles and given lectures on whiskey around the country. From his resume, the uninitiated might think Miller runs a quiet, cigar-and-snooker type joint, but Delilah's rocks. With DJ styles ranging from punk Mondays to play-your-demo Thursdays, the music is eclectic, and loud. Bourbon prices range from $2 specials (Jim Beam and Maker's Mark appear frequently) to $30 for the stuff you've never heard of.
Get Southern whiskey at Stanley's Kitchen & Tap
Sure, Stanley's is a popular spot for its brunches and dinner buffets, but don't count it out when it comes to bourbon. The bar boasts 100+ whiskeys, more than 50 of which are bourbons. Plenty of small batch favorites are available—Booker's, Baker's and Blanton's, to name a few—and bourbon makes its way into the food every now and then—bourbon chicken on Thursdays, and bourbon-glazed pork when the fancy strikes the chef. If you want a twist on the usual corn-mash, try a shot of Bernheim, a Kentucky wheat whiskey (not technically a bourbon), or stop in during the Kentucky Derby for a mint julep. Shot prices start at $6, but rumor has it a free bottle and shot glasses are left on the bar from time to time.
Make friends and lose clothes at Five Star Bar & Grill
This 30+ bourbon selection ranges from the stalwart Jim Beam brands to spirits like the Eagle Rare 10yr and Jefferson Reserve (top-end prices can reach $20), served in a decidedly hip indie-rock atmosphere, but without the pretension that tends to come with such an ineffable thing. A bourbon cocktail menu and bourbon-infused dinner are in the works, but for now it's liquor the way it was meant to be drunk—straight. After you've befriended the bartenders and had a few too many comped shots of Old Crow, head into the tattoo room—decorated with old-fashioned prints of sailor tattoos—and shed a few layers on the fully-functional stripper pole then refuel with specials like Monday's 50-cent mini-sandwiches.
Get yer smut, eggs and draft bourbon at the Twisted Spoke
Chicago's favorite "family biker bar" is also one of the city's best bourbon locales. Just digest this tidbit: Early Times is on tap. There really is a pressurized keg of bourbon hooked up to a draft system that is used for everything from cocktails to food preparation (and, doubtlessly, after-hours dares). Of the two Spoke locations, the Clark Street version has the wider bourbon selection (more than 50), but the Ogden spot has all of the fan favorites. Prices range from $5-$35 for a shot from the bottle, but a draft will cost a mere $2, everyday. Sip on a nice Van Winkle 20 yr. while you have your "smut and eggs," the Saturday midnight ritual that breaks out the breakfast menus and telecasts four decades' worth of hardcore, no-frills porno.
Have your bourbon and eat it too at Bourbon
Rounding out the list is the winner of the "duh" category, West Lakeview's Bourbon. 26 varieties of bourbon await your parched tongue, but what really stands out here is the food. Aiming for stylish comfort food, the menu is full of Southern treats, most of which are bourbon-infused. The alligator bites are a great alternative to calamari, and come with a Maker's Mark cinnamon chutney (as do all the sandwiches) that will be gone before you know it. The salads have a Jim Beam vinaigrette, and to top it all off, there's a Knob Creek creme brulee. A lot less rock-and-roll than the rest of the list, Bourbon is a place where you could wear a shirt with a collar and not look out of place.
Other spots to try:
Four Moon Tavern Offers a somewhat limited selection of bourbons, but its owner is a Blanton's devotee who has toured the distillery more than once.
Hyatt Regency Chicago/Hilton Chicago A few other downtown hotel bars have decent bourbon selections.
Le Bar Sofitel's bar has a selection of fine scotches and small-batch bourbons, and is a great place to rub elbows with the exceedingly wealthy.
Matchbox This tiny bar and the adjoining Silver Palm both have decent bourbon selections, and interesting seating options (hardly any and train car, respectively).
Matilda Serves a selection of small-batch bourbons, and won't let the DePaul kids in (ages 23 and up).
ROCKS Lincoln Park A more than adequate selection, and your on-the-rocks drinks are served with one big ice cube that takes longer to melt.