Fort Kaskaskia Road
Old Shawneetown, Illinois
This was a French and Indian trail which ran between Old Shawneetown located on the Ohio River, near the mouth of the Wabash River, and Cahokia, Illinois located across the Mississippi River from St. Louis. It was utilized as a migration route by settlers during the early part of the 19th century.
You could also go from Vandalia, IL to St. Louis on the Federal Trail.
If you Google "Pioneer Trails" you will find all types of options. There were also Mississippi Riverboat options. The OH river in Evansville, Indiana had riverboats going a number of places.http://www.lewisandclarkcountry.org/lewis_and_clark_IL_MO_KS...