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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.
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