The Travels with Kev Weekly Newsletter

Hello Reader,

One thing every traveler deals with is the budget — but are we actually looking at how we spend those dollars? Find out!

When “Cheaper” Isn’t Actually Cheaper

When I started, I made the classic rookie mistake — booking trips based on the lowest price. Sometimes it worked out fine. Other times… it got interesting.

What I didn't realize was that those 'cheap' fares sometimes cost me more than I thought.

Over time, I began paying attention to the full cost of those “cheap” fares—and it completely changed how I book travel.

Here’s a real example.

I have a tentative Fall trip to Lancaster, PA. I am not going directly. I am starting with the City of New Orleans from Chicago, IL, to New Orleans, LA, then the Crescent to Philly, and Keystone to my destination (there’s a story there for another time). When I priced it out, the simplest option for that first leg is to take the City of New Orleans straight from Chicago.

I could take a regional train (the Illini or the Saluki) from Chicago to Champaign in the morning or afternoon, then board the CONO there when it passes through later that night — saving about $45.

So… is $45 worth it?

That depends.

With the direct option, I can leave later, board in Chicago, settle into my roomette right away, and have dinner on the train shortly after departure—then wind down and fall asleep.

With the “cheaper” option, I’m sitting in Champaign, Illinois, for anywhere from 4 to 12 hours, depending on which regional train I took down.

Now, I do have friends there—that’s a real upside. But I’d also be figuring out dinner on my own, probably grabbing a coffee or a beer or two, all while hauling my bags around while I wait. Instead of being settled in for the night, I’m still killing time—and losing some shut-eye.

That $45 in savings starts disappearing pretty quickly.

For this trip, it’s not worth it.

But on a different trip—where I want that stop or have time to explore—the math flips completely. A long layover can be a highlight if I choose it on purpose.

You’ll see this everywhere in travel.

A slightly cheaper flight? Those savings can vanish during a layover, and you buy airport food and a beer. I'll admit—I've taken the cheaper connecting flight before because the layover airport had a brewery I love. It became part of the trip. Sometimes the "worst" option on paper is a fun choice in practice.

A cheaper hotel outside downtown? Great—until you factor in rideshares and the time it takes to get to where you actually want to be. Or the cost and hassle of finding parking.

Or… it might be perfect because you wanted something quieter.

That’s the point.

Don't let “cheaper” be the only piece of the decision.

Once you factor in meals, transportation, and time, are you saving money as you thought you would? How you’ll feel at the end of the day matters. Spending a little more means you’re closer to where you want to be. When you travel, you’re not just picking a fare—you’re designing the trip you want.

And that’s when you stop chasing the cheapest option and start booking the right one, and if that is the cheap one, that is a double score!

What is Kev Up To?

Friday, some friends from the brewery and I went down to Chicago for some "creamers," aka a pint or more of Guinness at the brewery in Chicago. We also went to a Mexican Brewery, which was pricey but tasty. Sometimes it is worth it.

It was nice to be on the train again, even a commuter train. But it was my friend's first time on this route, and for Aaron, it was his first time on Metra.

This week, I started looking into playing the organ for a silent film in October. I'm thinking of Phantom of the Opera — the 1929 version, not the Andrew Lloyd Webber version.

The 1929 Phantom is an updated version of the 1925 film, featuring color sequences and a synchronized soundtrack. I won't be using that soundtrack, though — I'll be creating a new one live on the organ.

Thank You!

Thanks for reading! Thanks to Charity K for visiting my Amazon wishlist and for getting me some wireless chargers.

If you're interested in helping me continue, you can click the green button below, visit my support page for more options, or join my Patreon! With a paid Patreon membership, you get a monthly postcard and more, and I just ordered new postcards.

Until Next Week!

Safe travels & Happy Planning,
Kev Monteith

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