Re: Chicago to St. Louis
 

In Springfield, there are lots of Abraham Lincoln sites; but your team might find this to be like Americans visiting Har Herzl or Sdeh Boker. My two favorites:
Abraham Lincoln Presidential Library and Museum: http://www.alplm.org

Lincoln's Tomb: http://www.lincolntomb.org

For a quick stop, weird outside "sculptures", and ice cream and snacks for sale: Pink Elephant Antique Mall in Livingston, IL: http://https://www.google.com/maps/p...d2c9d6d95c7dbd

Also - FYI, I am Malka and Eli Glas' brother-in-law's brother. Let me know if I can be of any help!

Re: Chicago to St. Louis
 

If you take the train (a reasonable option) you then have the disadvantage to not having transport around St Louis, thus limited to the local subway or walking. With a charter bus you also have a way around town if desired. AMTRAK is a quasi-private (meaning Government-subsidized but needs to try to make a profit) entity, and they are good but train travel is possibly the least desirable transit option in the USA.

Between those two cities, as many have noted, there isn't much but farmland.

I would at least inquire the cost from ORD to STL by air; it may be less than expected.