Club Café
The best listening room in Pittsburgh. Booked by Opus Productions. On the South Side.
The Shadow Lounge
Mostly DJs and theme nights. Has hosted some excellent song nights. East Liberty
The Thunderbird Café
Blues, jazz, rock, some good songwriters. Still smoky (watch for the "No smoking show" icon) . Lawrenceville.
The Backstage Bar
Small bar on the way into the Cabaret. Hosts a wide variety of artists with no cover, incluidng songwriters. Not a listening room, but a good stop in the Cultural District downtown.
Calliope
The Folk Song Society hosts national acts at the Carnegie Lecture Hall, but now has a great listening space at the Pittsburgh Center for the Arts. Oakland for the CLH, Shadyside for the PCA.
I listen to a lot of music. Here are some great places I've done it in the last few years, outside of my home town of Pittsburgh. If you're going to one of these towns, plan a night out around one of these venues--you mostly can't go wrong.
Old Town School of Folk Music (Chicago)
Joe's Pub (NYC)
The Bluebird Café (Nashville)
Mississippi Studios (Portland)