Chicago doesn't have a lot of venues for country music, so if that's what your ears crave, a trip to Carol's Pub is a must. In fact, they have both kinds of music at Carol's - country and western. It's a dive but the cheap beer, no cover, and late hours (open until 5 AM on Saturdays) bring in the weekend crowds, even if not necessarily country fans. The house band, the Diamondbacks, are in residence Friday through Sunday nights starting at 9 PM (Thursday is karaoke night), and they play the Johnny Cash and Waylon Jennings covers that get the people dancing.
To get to Carol's Pub in the Uptown neighborhood, your best bet would be to take a cab. I would not recommend that people who are not familiar with the area walk around in it, but if you must, go west from the red line train Wilson stop to Clark Street (seven blocks), turn right, and walk to Leland Avenue (one block). You can also take the Metra Union Pacific North line to the Ravenswood stop, walk east on Lawrence Avenue to Clark Street (four blocks), turn right, ans walk south to Leland Avenue (one block).
Carol's doesn't have a website, but here's the phone number: (773) 334-2402.