7 Best Places for Bourbon in Chicago

bourbon: Whiskey Thief

In the Venn diagram of liquor, all bourbon is whiskey, but not all whiskey is bourbon.

Bourbon is a very particular type of whiskey. The Federal Standards of Identity strictly defines what makes bourbon bourbon. First of all, the grain mash must be at least 51 percent corn; it must be distilled at no more than 160 proof; barreled at no more than 125 proof; and cannot contain any additives. Once distilled, bourbon must be aged in a new, charred oak barrel. Are you following all that? If you’re still with me, then you truly care about bourbon, and even though you knew all of those requirements already, you couldn’t help yourself because the word “bourbon” appears a number of times in the paragraph.

There are many great bars in the Chicago area, and a number of them pride themselves on their bourbon selection. Here are a few to check out when the mood strikes.

Barrelhouse Flat

2624 N. Lincoln Ave., Chicago, 773-857-0421

This dark but inviting craft cocktail bar is clearly patterned on bars of old rather than the aggressively loud and modern spots of the here and now (looking at you, all of River North). Here is where you will get your classic bourbon cocktail on, whether it’s a Boulevardier, Whiskey Smash, or, of course, the Mint Julep.

Big Star

1531 N. Damen, Chicago, 773-857-7120

They might be known for their mouth-watering tacos, but Big Star takes its bourbon very, very seriously. They’ve got 13 single barrel bourbon collabs ($10-$17), 32 Reserve bourbons, including five from the elusive Van Winkles (been living under a rock and haven’t heard of Pappy Van Winkle? Even the Pope is a fan!), and over 70 Kentucky bourbons from various producers. This is Ground Zero for Chicago bourbon lovers.

Billy Sunday

3143 W. Logan Blvd., Chicago, 773-661-2485

This joint is nothing if not full service. The beloved, much celebrated Logan Square cocktail bar will not only pour you a great bourbon, but will also help you with custom bar design in your own home, from designing and building it to carefully curating what’s stocked within. They also hold monthly cocktail classes (Cocktail 101, $50 per person) led by head bartender Stephanie Andrews. All this to say, they know just what they’re doing here, and they want to educate you as well as serve you.

Bub City

435 N. Clark St., Chicago, 312-610-4200; Parkway Bank Park, 5441 Park Place, Rosemont

When you see more than 100 varieties of whiskey on a menu, you know you’re in the right place. Sure, you can get a good smoked brisket sandwich here and listen to some righteous country music, but if you’re serious about your whiskey, this is a damn fine place to start. Try out a few with a whiskey flight, where you can compare and contrast.

Drawl Southern Cook House & Whiskey Room

2423 N. Clark St., Chicago, 773-687-8111

The newest addition to Chicago’s thriving whiskey scene is Drawl, which features seasonally driven, wood-fired Southern food in the front restaurant, and a connoissueur’s Whiskey Room for up to 20 guests in the back. Four different whiskey flights — including the Bourbon Sprawl ($18) and Bite the Bulleit ($25) — are offered, along with 30 well-curated bourbon options, and many other whiskey options of the rye and Scotch varieties. No TVs, no blaring music, just good food and drink in a convivial atmosphere. You won’t believe you’re in Lincoln Park.

Longman and Eagle

2657 N. Kedzie Ave., Chicago, 773-276-7110

Their stated philosophy: “Whiskey for your mouth, not our shelves.” This is serious business, folks. They have more than 400 whiskeys available, with a thoughtful collection of 100-plus rare and vintage bourbons for the aficionado. The word “comprehensive” doesn’t do justice to the selection here. And if you overindulge, they even have six “rooms at the inn” upstairs, and start serving “brunch” daily at 9 a.m. Full service, indeed.

Whiskey Thief

616 Davis St., Evanston, 847-859-2342

Named for the distiller’s sampling tool, this North Shore tavern has developed quite a following. Plush booths situated inside huge open barrels provide a respite from the bustle of a busy bar (and a TV or 12). More than 70 bottles of whiskey await your tastebuds; paired with chef Austin Baker’s “elevated” bar food, it’s a happy way to spend an evening. A cozy library area in the back of the restaurant doubles as The Barrel Room for private events of up to 60 people, and you can book group Mixology Classes ($45-$60 per person) during the week.

Julie Chernoff, Make It Better’s dining editor since its inception in 2007, graduated from Yale University with a degree in English — which she speaks fluently — and added a professional chef’s degree from the California Culinary Academy. She has worked for Boz ScaggsRick Bayless and Wolfgang Puck (not all at the same time); and sits on the boards of Les Dames d’Escoffier International and Northlight Theatre. She and husband Josh are empty nesters since adult kids Adam and Leah have flown the coop. Rosie the Cockapoo relishes the extra attention.