Because I write about bourbon and live in Chicago, people often ask me where they should go for bourbon when they visit Chicago. Here is my answer.
For package stores, there are really only two places you need to know. One is Sam’s. The main store, and the one I usually use, is at 1720 North Marcey Street, in the vicinity of North and Clybourn. They also have a store downtown at Roosevelt and State.
The other major retailer is Binny’s, which has many locations throughout the Chicago area. The location with which I am most familiar, and which I know always has a good bourbon selection, is on the north side at 3000 N. Clark. Their downtown store is the old Zimmermans at 213 W. Grand Ave.
Sam's and Binny's are the best places to go for selection and price.
Among hotel bars downtown, the Hyatt Regency (151 East Wacker Drive) and Hilton (720 South Michigan Avenue) both have good bourbon selections. Probably all of the hotel bars have pretty good selections, but I don't drink in hotel bars very often.
Also downtown The Berghoff is an old German restaurant, at 17 W. Adams. It has a limited bourbon selection but some of my favorites, not the least of which is their own private bottling, a Van Winkle wheater. The bar is beautiful too. It has been called, "perhaps what the bar in heaven looks like." The restaurant proper closed in 2006 but the bar is still open, as is the downstairs café.
In the Loop I also like Miller's Pub (134 S. Wabash Street). The bourbon selection is only so-so (Maker's, Knob Creek and Old Grand-Dad BIB are the best bets), but it's a real bar (and also a pretty good restaurant), little changed in 50 years, cheap for a downtown joint, with convivial and professional drink slingers. It's civilized without being pretentious. For easy reference, it's a few steps south of the Wabash Street entrance to the Palmer House.
Outside the Loop, in the River North area, I'm fond of the Clark Street Ale House (742 N. Clark Street), which has a good selection of beer and whiskey, nice atmosphere, and is easy walking distance to some good blues bars, restaurants, and convenient public transportation. It's an easy way to get a little bit out of the Loop and Michigan Avenue neighborhoods where most visitors stay.
In Lincoln Park, Stanley's is a good choice. It is at the venerable six-corner intersection of Lincoln, Armitage and Sedgwick. I call it "venerable," because there have always been several good, big, popular bars at or very near that intersection. Stanley's has a large, eccentric bourbon collection (Old Heaven Hill BIB on a Chicago back bar?) and a menu of "American Classic" cuisine that is a cut or two above pub grub.
Another Chicago place that pays proper respect to America's native spirit is Twisted Spoke, 501 N. Ogden (at Grand). It's the only place I know of that has Jim Beam on tap. It's also a decent restaurant.
Far and away the best bourbon selection in town is at an unexpected place called Delilah’s, at 2771 N. Lincoln Avenue (just south of Diversey). If you imagine a bourbon bar as looking like an English men’s club, prepare for a shock. Delilah’s is more of a punk rock joint, but they have probably twice as many bourbons on offer as anyone else in town. Any lover of fine drink and serious rock and roll is always welcome.
Delilah's doesn't serve food, but there's a Gino's East pizza right across the street.
All of the above are easily reached from downtown by cab or public transportation.