Travel is an area where, as we say in England, it’s possible to be "penny wise and pound foolish". You can always travel cheaply, but sometimes cheap doesn’t mean inexpensive when you consider the big picture.
For example, on my recent trip to Boston, I considered driving to save money. It’s 700 miles or so. With my car, that’s around 22 gallons of gas, or $70 or so each way. But the drive would take 12+ hours, so (a) I’d lose more than a day of time just getting there and back and (b) I’d be wiped out for my pitch meetings.
Not to mention that driving in Boston is a pain and parking is outrageous. So $140 round trip, $80-100 in parking and wasted time. All in all, not worth the the $20-50 I’d save by not flying.
Another (historical) example: there’s a Motel 6 on the edge of Vegas, not far from the airport. I used to do a lot of conventions in Vegas and while the tradeshows are on, the hotel rates are through the roof. One year, I booked all of us in to the Motel 6. The burned out car in the back lot should have been a clue as to what we were in for. But the hooker (so not kidding) banging on my co-worker’s door at 2am was just one of the many "features" of the place. Needless to say, it was not a restful place to stay.
So thought #1: bear in mind that the purpose of the trip usually isn’t to save money, it’s to go and take a meeting, do a pitch etc. Cheap is good, but not if it undermines your ability to function at the event that is the reason for your trip.
Job 1 is getting to your destination. If you can’t easily drive (or share the drive) flying is usually the only alternative. I’m a big fan of Southwest airlines for one simple reason: if you need to change your flight, they don’t penalize you, you just pay the difference between the price you paid and the full fare for the segment of your trip you changed.
Compare and contrast: I had a previous Boston trip booked that I had to cancel. I was flying US Air and the ticket was a bargain at $180. Cancelling incurs an automatic $100 change fee AND you have to re-book through a phone agent. The agents cannot offer web-pricing, so you pay full whack for the ticket. In this case the agent price was more than $80 over the web price. The math savvy amongst you will have realized that this makes the ticket worthless. On Southwest, I once had to change an outbound flight. No fee and the phone agents have access to the same prices as the website. I paid $60 to change the ticket.
I also like Southwest because generally treat you like a human being.
Prices for flights change all the time. But generally you have to be 2 weeks ahead to get a good deal and 7 days ahead to get an okay deal. Less than 7 days and you’ll most likely pay top dollar. I’m not a fan of Priceline for flights because you can’t specify flight times, but if your schedule is flexible it might be worth looking at.
Last but not least, get yourself a frequent flyer card for whichever airlines you travel on. You’ll be suprised how fast the miles can rack up.
Your second task is finding a place to stay. If you can call in a favor, do so. It’s cheaper to take a buddy to dinner than to stay in a hotel.
For most cities I do like Priceline. You can pick a part of town, star level and specific dates. The only caveat is that you get way better pricing if you wait until the last minute. On my recent trip to Boston, I stayed in Waltham for $80 (regular price $120) and downtown for $150 (regular $450+).
Before your rely on Priceline, check their "name your price" map for your destination. In Manhattan and Boston, it works well. In Vegas, the area they consider on "the strip" gets into some bad parts of town that are a long way from anywhere you are likely to want to be.
Public transport works sometimes. For example, on my last trip I need to stop in Providence, RI. To get to Boston, I took the train — it takes 40 minutes or less and costs $12. I didn’t want to rent and park a car in downtown, so mostly I walked or took a cab.
The last day of my trip was in Waltham. The commuter rail goes out there, but the trains are pretty infrequent and the station was miles from my meetings, so a car was the only real choice. Not many folks know this, but Priceline is also brilliant for rental cars. You have to pick up at an airport, but you can specify dates and type of vehicle (compact, mid-sive, SUV etc). I paid $25 plus tax for a mid-size from Budget. Rack rate is $55 plus tax. In Phoenix and Raleigh I’ve rented full size cars and SUVs for as little as $20 per day. Last minute gets the best price.
Check the details of your credit cards. Many have some level of automatic coverage for rental cars, which can save you buying the rip-off insurance from the rental company. If you’re driving a lot, consider pre-paying the tank of gas — it’s usually cheaper than gas at the gas station. But if you aren’t doing the miles, opt to bring it back full.
Two other thoughts: you can often rent a GPS for $12 or so — often very worthwhile if you don’t know your way around. I’ve also heard good things about Zip Car — you can rent cars by the hour and they’re reasonably priced.
The only caveat with Priceline is that it is pre-paid and non-refundable. If you book a car or hotel and then change your plans, you’ll lose your money.
A company I used to work for had a great travel planning spreadsheet. You would try to find the best priced travel option, typically choosing from Flight A, Flight B, or drive. The spreadsheet took into account the travel time for each method, multiplied by a set hourly rate, so a real financial cost was tied to the travel time. Then, the travel methods were evaluated based on the sum of those costs.