Due to a conflict I forgot about, the date will be March 24! Now to decide where to meet.
My initial thoughts were perhaps Gateway Classic Cars in Crete or Volo Auto Museum in Volo. If you know of any other place like that, feel free to suggest it!
Update: I also found a place called Klairmont Kollection which seems fairly interesting, downside is that it’s $21/person and it appears that tickets must be purchased ahead of time.
Update 2: Also found Chicago Vintage Motor Carriages which has some very classy classic cars.