How Kev Books His Amtrak Adventures


The Travels with Kev Weekly Newsletter

Hello Reader,

I hope you had a great week! After more than a decade of riding Amtrak, I’ve developed a few habits for booking trips. This week’s article walks through how I book tickets, use passes, and plan more complex adventures.

How Does Kev Book Amtrak Adventure?

There are several ways to book Amtrak trips, and the option I choose depends on the type of trip I’m taking.

Online vs. Calling

I rarely call unless the booking tools are having trouble with something specific, or doing something complex like trying to book two nearby roomettes. After more than 14 years of traveling with Amtrak, booking online feels more natural to me and is usually the easiest option.

App vs. Website

The trip itself usually determines which I use.

For coach or business-class trips, I typically use the app unless I’m already at the computer — for example, when booking a quick trip from Sturtevant to Chicago or Milwaukee.

For any trip with a sleeping accommodation or multiple segments, I use the website — including the mobile version for phones and tablets — because the app often does not show all available rooms, at least not recently.

The website is also where I compare roomettes and bedrooms. The price difference is not always what you might expect. I booked a bedroom on the Floridian during the advance booking window, before service even started, and it was cheaper than the roomette on the same train. Other times, I have seen bedrooms cost only about $50 more, which can be worth it for the extra space and private bathroom.

One-Way vs. Round-Trip

I lean toward one-way tickets unless I’m confident that nothing about the return trip will change. That gives me the flexibility to adjust the return trip on my own without calling Amtrak.

If I’m heading to St. Louis for lunch, for example, I already know I’ll be coming back that same day, so booking a round trip makes sense.

But for a more complex trip — say Los Angeles to Lancaster, Pennsylvania, with the Cardinal back to Chicago on the return — I’ll usually book each leg as a separate one-way ticket. That gives me more flexibility if plans change along the way.

Multi-Ride Passes

Amtrak also offers multi-ride passes on some regional routes, which can save you real money if you travel the same corridor frequently. I’ve used these quite a bit on the Hiawatha.

A monthly pass gives you a round-trip ride on that route for 30 days. For commuters, that is essentially a round trip every workday, with room for extra trips.

There is also a ten-ride pass that includes ten one-way rides and is valid for 45 or 90 days, depending on the route. That works out to five round-trip passes on a single pass.

If you are planning a larger multi-stop adventure rather than traveling back and forth on the same route, Amtrak also offers the USA Rail Pass, which includes 10 travel segments within 30 days.

Multi-City Tickets

Multi-city bookings are a useful tool, but you need to use them carefully.

Here’s an example. Let’s say I’m traveling from Sturtevant to New Orleans. Amtrak’s standard search might place me on a Hiawatha that leaves little time to visit friends in Chicago before boarding the City of New Orleans. If I want extra time in Chicago, a multi-city booking lets me add an earlier Hiawatha while keeping the trip on a single reservation.

It is also worth checking multi-city pricing for East Coast trips. For a while, travelers could sometimes get a better price by booking everything together rather than buying separate tickets.

Multi-city itineraries can also work well for stopovers. If you want to spend a few days in Washington, DC, on your way from Chicago to Kissimmee, Florida, you can keep the entire Floridian journey on a single itinerary and add extra time to the trip.

The catch is that multi-city bookings do not guarantee connections. You can technically misuse the system — for example, by booking the Borealis to Chicago at 7:26 p.m. and connecting to the 8:05 p.m. The City of New Orleans has very little buffer time. That might work when trains run on time, but if delays occur, you are usually responsible for handling the missed connection yourself.

What Should You Do?

There are several ways to book Amtrak trips, and these are the methods I use most often. The best approach for your trip is the one that matches your comfort level, budget, and travel style.

Some travelers enjoy planning every detail themselves, while others would rather have someone guide them through the process. If you want your entire trip arranged for you, a travel agent can be a great option. Personally, I prefer handling the planning myself.

And if you need help along the way, there is nothing wrong with calling Amtrak, visiting a staffed station, or asking a travel agent for assistance.

What Is Kev Up To?

I'm happy to report that my return flight was forgettable, and I'm glad. As much as I love a good story, I also like it when everything goes as planned.

This week was mostly calm. On Monday, I had a few beers at the local brewery's beer garden with friends. It was nice to sit outside, listen to the river, and watch a CN train pass by every so often.

As I mentioned last week, my sister is moving from Florida to Wisconsin. This has been in the works for months, but there's been a change (from August to July) — it all got moved up, which is why my trip with Mackenzie got pushed.

I also had to book a flight back to my sister because I might need to help finish loading things and whatnot, and to help drive my sister and the twins back if my brother-in-law cannot. I paid more for a refundable flight in case I do not need to go, and I do not have any flights planned, so I did not want a travel credit.

Thank You!

If you'd like to help keep Travels with Kev rolling, you can click the green button below, visit my support page, or join Patreon.

Anyone who supports via PayPal gets a postcard. If you use the button below and reply to the email, I’ll send one your way, too. Patreon members receive a postcard every month as part of their membership. I’m about to create a fresh batch of postcards that I’m excited to start sending out!

Until Next Week!

Safe travels & Happy Planning,
Kev Monteith

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Kev’s Amtrak Long-Distance Quick Guide - Updated January 2026

Travels with Kev is independent and not affiliated with Amtrak or VIA Rail. The tips and information here are based on my personal experience. Always verify Amtrak's and VIA Rail's current policies, deals, and schedules before booking.

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