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I think you'll definitely enjoy either of those choices, and every man deserves to have a good boot, but it does seem like you've drifted from your original parameters. IMO neither a chukka nor chelsea will be any easier than a plain old lace-up when it comes to airport security. Are there any other considerations with regards to your travels? Are you taking long distance flights? Are the travel shoes also shoes that you want to wear while on the trip and therefore need to fit in with business outfits? When I'm flying more than 1 hour, I always slip off my shoes for the flight. I personally find that my chelseas can be more cumbersome to take off and put on, especially in the cramped confines of an airplane seat; unless we're talking business class international or above. If you're taking relatively short trips, say a few days at a time; then I suppose you do want your travel shoes to pull double-duty and be something you can wear while on the trip. In that case, a chelsea can fit right in with a suit for sure. But for a longer trip, the suede loafer or driving shoe can also double as a slipper of sorts when staying in a hotel for days or weeks on end. Or, if after a long day of business meetings you want to dress down with a sweater and odd trousers for a light snack and drink at the hotel bar, the more casual shoe can fit right in. Just my $.25...
Here's my challenge; I'd pickup loafers, but I can't bring myself to spend much on them (why didn't I BIN when Ron had those bombay loafers for $100?!?!?). The Chelseas on the other hand, are nice enough to be a casual choice in addition to travel and easier to justify.
...and look at the boots in their own light.
I bought a pair of suede EG Parson's from Whnay that has the elastic gorge - so we'll see if that'll do.