Is driving cheaper than flying? Once you add up the costs, the savings may not materialize, but your headache might.

Wanna travel from Charlotte to “Where the Bears Are” in Fort Lauderdale? How about from Denver to the famous (and infamous) Habana Inn in Oklahoma City? Or what about going from San Jose to “The Dinah” in Palm Springs?

Conventional wisdom says that driving is always cheaper than flying. But given today’s high gas prices (which only promise to go higher) and the ever-competitive prices for commercial flights, you may find that it’s cheaper — and less of a hassle — to fly to your destination, especially when you’ve put in some time doing some proper research into the cheapest flights possible, looking at sites like Finnair lennot and others can allow you to find the cheap flights that can make your travels as inexpensive as possible.

Making the call

Here’s a rule of thumb: if you’re traveling alone and your car trip would require at least one stay at a hotel, you’re probably better off flying. When you drive, there are costs for food, lodging, and, of course, gasoline. There are also the dangers of traveling alone — the most dangerous of which is drifting into complacency behind the wheel. It’s best to book hotels as far in advance as you can. For example, if you know you need to go on a business trip to Evanston in September, book somewhere like the Holiday Inn hotel in Evanston, IL a few months before you go. This ensures you get the room of your choice, after all, you wouldn’t want to be left with no accommodation after traveling so far!

If there are two or more people traveling, the economics of driving improve, but may not be as wonderful as you think.

If your trip will be between six and eight hours each way and there are at least two people in the car, your best option is usually to drive. Ideally, you’ll burn through just two tanks of gas per day on a full day of driving. Two tanks of gas will run anywhere from $40 to $80 per fill-up, depending on what you drive. Factor in cheap eats of about $20 per person per day, and you could reasonably make the trip, back and forth, for around $325 for both people. Round it up to $350, and you still come out better than if you purchased two airline tickets, averaging $250 for each round-trip. (If you’re not flying from a major airport like SFO or DFW, the cost of those tickets would likely be higher.)

However, when there are two of you traveling by car and the trip requires an overnight stay, the cost-benefit analysis gets trickier. Plan on at least four tanks of gas each way for a two-day drive, one hotel for a minimum of $50 a night (times two) and meals at $20 a day per person. On the cheap end, that could be as little as $340 for the entire trip, but that’s not likely. Taxes, especially for lodging, can be exorbitant. And I’ve never been able to drive long distances without plenty of stops for water, bathrooms, and plain old rest and relaxation. All those things add to your time — and your costs.

As you approach $400 in this scenario, it may be cheaper and less of a hassle to splurge on a couple of plane tickets. True, you might save money by driving if you need a car at your destination, but remember, many rental car companies can get you rates as low as $30 a day. It might be easier to fly and rent a car at the airport.

(If you’re going to be staying in a city with good public transit like Chicago or San Francisco, renting a car probably isn’t a good idea and can cost you a small fortune in parking and frustration. In Denver or Dallas, however, a car is almost a necessity.)

If you have three or four people in the car, driving is always cheaper than flying. The only drawback — which could be a big one — is that you’ll be cooped up in a car for many, many hours with several other people, who will most likely get cranky as the day wears on. Make sure you have good A/C, a great selection of music, and a clear understanding of who gets to play DJ.

Other considerations include:

• Furniture or other large items. If you are transporting big stuff, take a car. Shipping and/or airline fees really will eat you alive, especially if it’s fragile. The other option is to ship your car with some of your possessions within, for this you’d have to look into different car shipping companies to find the best prices and benefits.
• How will the costs be split? When traveling with friends or family, be sure to discuss ahead of time how each item will be paid. When in doubt, plan to pick up the costs yourself and, hopefully, get reimbursed later.
• Do you really want to travel in a cramped car with your companions? Your friends are like medications: overdosing can cause serious ailments. Flying affords people to be alone while traveling together. Not so in a car, even in a Park Avenue. Think about what will really make you happy, or at least what will keep you from going ballistic. Plus, if your budget allows, and if you are someone that values their personal space, you might even want to consider doing some research into securing a private jet rental. Besides, when it comes to flying, nothing beats the luxury of a private jet.
• Whenever planning a budget, always account for unknown costs. When driving, there is no flight attendant or ticket agent to help you, so you should allocate an additional 30% of your budget for unplanned costs. That alone may push you into the arms of an airline ticket agent, who just might be gay and cute.

So, how should you approach your upcoming trip?

Start by checking travel websites to gauge airfare prices. Southwest Airlines is always good for cheap tickets, especially if all you need is a one-way. Other websites like Orbitz.com offer a convenient way to compare prices, and they’re always trying to reach the LGBT market.

And if, after everything, you opt for the road trip, be sure to invest in a roadside assistance program like AAA. Because sure, you can change your own tires, but how well will that grease under your fingernails go over at the White Party?