This Train Route From Chicago To New Orleans Offers Scenic Lake Views And Music History

The City of New Orleans isn't just a destination for Amtrak, which also has an overnight train that goes by that name. The train travels between Chicago and New Orleans on what was once the "Main Line of Mid-America," back when the Illinois Central Railroad operated it. Riding the full length of that route takes over 19 hours as the train runs inland but roughly parallel to the Mississippi River for 900-plus miles. In 2024, the City of New Orleans had the highest percentage of on-time customers among Amtrak's long-distance routes, though it still fell 1% below the Federal Railroad Administration's 80% benchmark.

The train has a Sightseer Lounge up top, where you can take in views of Louisiana's Lake Pontchartrain from panoramic windows. There's a long ride leading up to that, however, and the views might not be worth it for everyone. Amtrak's main selling point for it is that it offers a journey "through the heart of our nation's musical heritage." Bookending Chicago blues with Memphis rock 'n' roll and New Orleans jazz, the train even stops in McComb, Mississippi, the birthplace of pop star Britney Spears. Its musical journey begins with its name, which the fledgling Amtrak retired in 1971, only to resurrect it a decade later after it enjoyed popularity in a hit song written by Chicago folk singer Steve Goodman.

Willie Nelson released a Grammy-nominated cover of the song in 1984, while the version performed by Arlo Guthrie spent 16 weeks on the Billboard music charts in 1972. After Hurricane Katrina struck in 2005, Guthrie took the lyrics about "ridin' on the City of New Orleans" to heart, boarding Amtrak for a benefit concert tour of the same route. Former U.S. president Bill Clinton — who used Amtrak for his own whistle-stop tour during his reelection campaign — even listed "City of New Orleans" as one of the essential American songs for the country's 250th birthday in 2026 (via CBS News).

The City of New Orleans train chugs across five U.S. states: Illinois, Kentucky, Tennessee, Mississippi, and Louisiana. Since it leaves Chicago after 10 p.m., you'll likely be riding in the dark through all of Illinois. In late spring and early to mid-summer, when daylight hours are longer, you might be able to catch the sunrise as the train pulls through Fulton, Kentucky, en route to Memphis and New Orleans' rich musical history.

Business Insider named it Louisiana's most beautiful train ride, since some of the best scenery comes there as the train crosses Lake Maurepas and skirts the edge of Lake Pontchartrain. Along the way, you'll see what Vacations by Rail calls "cornfields" and "quintessential small-town scenes" and what Reddit calls "backyard America," "swamps and inlets," and "the poorest region of the US." On Facebook, Amtrak has marketed the City of New Orleans route as a way to "follow the Mississippi River all the way down to the Delta." You should be able to preview the route on Google Maps, filtering the results by train (under "Options"), and using Union Station, Chicago, as a starting point and Union Passenger Terminal, New Orleans, as an endpoint.

When you zoom in close on the map, you can see how the actual train route isn't exactly hugging the river, so much as it's running alongside it at a distance. Passengers expecting to behold majestic views of the mighty Mississippi might be disappointed. As a service attendant on the Amtrak Unlimited forum once wrote, "In the late summer, if someone points out exactly where to look you can 'imagine' you are looking at the Mississippi." At night, the train does cross the Ohio River near where it meets the Mississippi, just south of Cairo, Illinois. However, as a sleepy engineer on the same forum wrote, "You can see that you are crossing a very wide river, but not a whole lot beyond that."

Though it's not the same "southbound odyssey" immortalized in song, you could have a more immediate payoff, scenery-wise, by riding the City of New Orleans in the opposite direction, past Lake Pontchartrain first. Since the train's current northbound timetable has it departing from New Orleans at 3:15 p.m. and arriving in Chicago at 11:15 a.m., this should allow you to see both cities in the daytime (barring delays from freight train interference). Comparing the two routes, one Redditor says, "You see a bit more of Mississippi including the delta southbound, but it isn't really that scenic or anything." Another recommends grabbing "a window seat on the right side for the best views as you are leaving" on the northbound train.

The "City of New Orleans" song has a line about "changin' cars in Memphis, Tennessee," and you might also want to do that to break up the long train ride. There are at least half a dozen spots every Elvis fan needs to visit on a Memphis stop-off. However, before visiting this dangerous southern U.S. city, tourists should consider that they'll be arriving there after midnight when northbound. You'll know you're leaving Memphis when you see the big "M" — more specifically, the lights dotting the double-arched Hernando de Soto Bridge.

Even if you ride straight through without stopping in Memphis, those bridge lights should still be visible on your left. They could be your best indication that you're following the Mississippi, since the bridge spans the river from Tennessee to neighboring Arkansas. Later, when the sun is up and the train rolls into Chicago, you might spot landmarks like Soldier Field, where "da Bears" play football in a stadium that evokes the Roman Colosseum with exterior colonnades. Keep your eyes peeled for the twin antenna masts atop Willis Tower — formerly Sears Tower, which stood as the world's tallest skyscraper for 25 years.