More power to you to getting a permit in a state that has been so hostile to concealed carry. If it were me, I believe I would move out of Illinois. unless I was say law enforcement which I am not. I also only carry revolvers. For the 2nd gun I recommend the S&W 642 airweight stainless steel 15 oz revolver. It works well in a pocket holster if the pockets are big enough to conceal well, which is probably going to be an issue as well.
The main carry weapon I think I would get would be maybe a S&W 357 that shoots 44 mag and 38 Spl. Was just looking in a gunshop the other day and saw one. If I were going to be one of the first to conceal carry in Illinois and lived there, I would be very careful to make sure of deep concealment. I carry a CA 44 Spl in a paddle holster under a harbar bay shirt in Texas, but I would not want to try that in Illinois given its anti gun history.
Incidentally Illinois I expect will not have a reciprocal aggreement with Texas, and I travel to no state that does not have one with Texas. So I say stick with very concealable revolvers and methods of concealment. I wonder what new taxes Illinois may levy there on gun owners.