I've had very good luck finding and selling a few bikes on Craiglist, myself. Also found the best car and best car deal I've ever found on Chicago Craiglist a few years ago, and that is in several decades of car shopping!
Also, you're fortunate to have a lot of great bike shops of all sorts in Chicago, with many very experienced employees to consult. Good luck on your quest and sale.
Finally, if donating your bike becomes an option in these times, you may want to check with West Town Bikes on the north side, or Working Bikes Co-op on the south side. Again, good luck.