I would drive due to you can leave when you want and you can control where you go no flight delays or anything like that.
IJCDMK
Memphis, TN. From there you can take the City of New Orleans north to Carbondale or Chicago or south to New Orleans.
The only train to Tennessee from Chicago is the City of New Orleans. It is 442 miles to Newbern-Dyersburg and 528 miles to Memphis. It takes almost 8 hours to get to Newbern and 10 1/2 hours to get to Memphis.
Unfortunately, there is no Amtrak train service to Nashville. The old Union Station is now a Wyndham hotel and that is available for viewing. The closest Amtrak station is in Newburn, TN. From there you can take the City Of New Orleans north to Carbondale and Chicago or south to Memphis or New Orleans.
Check
Fulton, KY. From there you can take the City of New Orleans north to Carbondale and Chicago or south to Memphis or New Orleans.
Night Train to Memphis - 1946 is rated/received certificates of: USA:Approved USA:Passed (National Board of Review)
Night Train to Memphis - 1946 was released on: USA: 12 July 1946 USA: 15 February 1949 (re-release)
"Memphis Time" by Gin Blossoms It's on their album "Congratulations I'm Sorry", which came out in 1996.
About an hour
10 seconds
on a train