If you currently do or have ever used a train to commute for work, a 19 hour train ride might sound like the worst idea you could ever have. 19 hours squashed up in a seat. Sure you can walk around. Sure there’ll be a few stops. But seriously, 19 hours? And yet that’s exactly what you’ll get when you an Amtrak train from Chicago to New Orleans.

Ok, tell me more about this train from Chicago to New
Orleans idea…

Here in the UK, the majority of my train experience extends to the always-packed-to-capacity Chiltern line into Marylebone, London. And when necessary, onwards on the always-packed-to-capacity tube. My poor credit card will be forced to take a hammering in cabs to avoid the Underground at all costs if I can get away with it. First world problems and all that.

But that’s for work. On holiday in another country though, the thought of taking a long train journey vacation seems fresh, mysterious and generally quite fascinating. Just think of all the scenery! As a 30-something female travelling alone, I love the flexibility of being able to fully tailor my holidays to my exact desires. No package holidays for me. But you’re unlikely to find the trains as an offered form of holiday transport if you’re just looking through deals on the regular travel sites in Britain. If you’re after a fly-drive to Orlando on the other hand, you’ll have considerably more luck.

Amtrak booking success

And so, i formed the outline of this particular trip that was going to begin in Illinois and end in Georgia. With 2 trans-Atlantic and 3 domestic flights to take, I decided to bite the bullet and get the train from Chicago to New Orleans. Just a solid 900 miles and 19 hours of pure train fun!

train from Chicago to New Orleans Greenwood Mississippi Amtrak station
Double-decker Amtrak sleeper train

I couldn’t pass up the opportunity to treat myself. So rather than book a regular seat (that’s just asking for a lifetime of back problems), I went ahead and booked an Amtrak bedroom. A family-sized room – if you are indeed a family of hobbits. For the most part I was drawn to this particular accommodation because it came with a private bathroom and full fold down beds. Though regular seats are super cheap, the upgrade to the room still cost around the same as it would have cost me to fly. So really, it was still a bargain!

You’re doing what?

Feeling rather pleased with my grand plans of travelling the States by train, when I relayed my intentions to colleagues and friends, I was mostly met with bewilderment. “Ooh I couldn’t do that” and more perplexingly, “ooh you’re so brave”. I didn’t really question why this made me brave at the time, but it’s something I hear a lot when I go away by myself. I came to realise that the idea of travelling or holidaying solo, for a lot of people, is just not something they’d consider. Either because they have a family/a significant other/friends (with the same interests/budget – I have friends, honest 😋). Or they have a fear. And thus here I am to impart some – not always wise – but hopefully helpful anecdotes of my solo-travel experiences.

Chicago in the sunshine

train from Chicago to New Orleans
Glorious views across Chicago from the aquarium.

I digress. My holiday dates soon came around and I was all set to go. First up, I had 4 thoroughly enjoyable days in Chicago. It was early November and particularly balmy for the time of year. Which coming from the rain and cold of London, made for a refreshing and welcome change of weather pace.

Headed for union station

And then the night came. This was it. I was finally ready to get my Amtrak on. I took a cab (definitely should have Uber’d) to Union Station from the Thompson Hotel. Once the cabbie eventually found where he was going, he dropped me outside… The completely wrong entrance.

If you’ve never been to Union Station and you’re going to turn up at night, be prepared to get a little lost. Do find someone immediately to ask where to get Amtrak from. Or if you enjoy a good walk, do as I did and walk round the buildings 5 times first. And still not have figured out where you’re going. To be fair, the station was undergoing a lot of re-construction at the time so it might not be quite as complicated as I can now recall. Or perhaps navigation is just not my forte!

train from Chicago to New Orleans Inside Union Station Chicago
Getting the train from Chicago to New Orleans: you will struggle to find a more impressive train station than Union Station in Chicago. Unleash your inner architectural geek and marvel at the vaulted ceilings and soft mood lighting.

I finally managed to find where I needed to go and lugged my bags downstairs to the ground floor. There is a lift don’t worry, I was just being dramatic. I didn’t really know what to expect. Is it like a bus station or an airport? How do i actually check-in? Where does my luggage go?

Check-in at chicago union station

The set up was a lot like a (small) airport. Including a number of check-in desks and a conveyor belt behind to sort the checked bags. I rocked up to the first free attendant. With a big smile on my face i proudly announced I was checking in for the 8pm train to New Orleans. Like I was the first ever person to do so. He looked at me like I had asked to kill his dog.

Once we got over that first-date awkwardness, he kindly went about printing my tickets for me. I hadn’t quite managed to get round to it before leaving home. Then I had to additionally tag all 4 bags with special Amtrak tags. I only had one suitcase but also 2 small and one medium piece of hand luggage.

5 minutes later I was done, checked in and ready to get going… In 2 hours when the train was due to leave. Bags need to be checked in a minimum of 45 mins before departure but this can vary by station so do always double check before you leave. I was obviously a bit over-excited in this instance.

Are we there yet?

Looking to waste some time, I wandered back up and outside and quickly found myself faced with…not a whole lot. My hand luggage wasn’t particularly conducive to meandering around and exploring easily. But you could venture a little further if you have time and travel light.

Back inside I went and made my way down to the Amtrak waiting room via a small convenience shop to pick up a drink. And a (definitely high-brow, definitely not US Weekly) magazine.

The waiting room is sizeable with lots of seating depending on the time of day. It was in a bit of a forlorn state at the time. There were those harsh yellow lights that give you a headache in 2 minutes. And it definitely smelled a bit funny. But I don’t mind things like that and it might have had a lick of paint during the ongoing restoration work.

I was much more interested in people-watching the sometimes bizarre mix of Amtrakkers around me. Huge groups of families arguing, a young boy backpacking, construction workers, an Amish couple. I was almost disappointed when the call for the train came and I had to tear myself away from the guy in front of me who was casually brushing his toupee as if he was stroking a cat.

But so the call did come. And after lining up in the allotted space ready for the staff to check my ticket and direct me to my sleeper car…It was goodbye Chicago, hello adventure.

Learn more about Chicago Union Station here.

Part 2 coming very soon! Feel free to ask questions in the comments! 👍

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