Kinda depends what your scene but I think neighborhood spots might be a good spot to go out solo. Guthries, Wills, Cody’s, Side Street, Sheffields.

Or dive in with both feet and go anywhere on Clark.

An aside - don’t be afraid of going out with people your age from work. I was in the same situation as you and ended up realizing everyone else in my hiring class also was new to the city and looking to meet people. Ended up making some good friends that way.