Why'd you fly from O'Hare to Midway, and other airfare tricks

Tired of your lousy commute through the congested highways of Chicago? For as little as $200, you can catch a flight from O'Hare and land at Midway. Sure, you'll have to pass through Detroit, Dallas, or Milwaukee on the way, but you can earn thousands of frequent flier miles, which will come in handy if you're gunning for elite status at this time of the year.

Plus, flying from O'Hare to Midway is a better deal than what American is pitching its most loyal customers. For between $450 and $750, depending on your status and how much you've flown already this year, American will let you renew your Platinum or Gold membership, which allows you to enjoy first-class upgrades and priority boarding.

If you're close to the regular qualification levels, however, it may be worth forgoing American's offer and booking a flight known as a "mileage run" instead. That's a trip, like the O'Hare to Midway example, that you take for the sole purpose of earning frequent flier benefits. Typically, frequent flier junkies will make a mileage run to qualify for elite status at the end of the year, or if there's a particularly lucrative offer (say double miles) that they can combine with a lower-than-normal fare. They might travel with an extra-long connection that earns them bonus miles, such as New York to London, via Los Angeles, or they might make an overnight or same-day trip to a city that's just far enough away to earn them the miles they need.

While flying from O'Hare to Midway may sound ridiculous, the airlines will be perfectly happy to pocket your money and let you board the plane. (You'll have to book on Orbitz or another site that lets you choose specific flight combinations to make up an itinerary.) There are other booking tricks, however, that the airlines frown upon, and in some cases will prevent you from using. You can try these strategies to find lower fares, but I don't recommend them unless you're sure the airlines won't catch on. If they do, you run the risk that your ticket will be declared invalid, and you may have to purchase a new one to get home.

The most common airfare booking trick is called "back-to-back ticketing." Let's say you want to fly from Chicago to New York for an overnight business trip. Ordinarily you'd have to buy a high-fare unrestricted ticket, for at least $600. But instead, you can buy two round-trip tickets, one leaving from Chicago and one from New York, and both including a Saturday-night stay. You'd use just the first half of each ticket to travel on the days you want, saving a few hundred bucks in the process. If you're going to employ this tactic, be sure to use different airlines that aren't partners, for example, Southwest and American. Otherwise, the reservations systems will flag your booking, and you may be asked to pay an additional fee before you fly.

A second trick, most useful on one-way trips, employs what's known as "hidden cities." Let's say that you need to fly from Dallas to Chicago, but you realize that the fare's actually much cheaper if you buy a ticket from Dallas to Minneapolis. What you can do is arrange your ticket to include a layover in Chicago, and then simply intentionally miss your connecting flight. This doesn't work on round-trip tickets, because as soon as you miss a leg of your itinerary, the remainder of your ticket will be automatically cancelled.

Being creative about how you book your fare can save money on your airfare, earn you more miles, or get you closer to elite status. But if none of those goals are on your travel to-do list today, at least you'll have something to mull over while you're stuck in traffic on the long commute home. And that just might make a trip from O'Hare to Midway sound like a brilliant idea.