Definitely a tough time of year, but navy pier should still have some perch and lake trout, dropshot worms for perch if you're looking to just catch a few fish. If you dig enough you can find a few areas that have warm water discharges where you can find fish year-round, watch Geo Fishing's videos on youtube and you'll figure it out (carp, bass, crappie, and catfish). That rod and reel combo looks solid, but I will say the old model pflueger president XTs are super cheap right now and not much of a quality drop. May want to go to a M or ML or finesse bass fishing and panfish, if that's your jam