If you aren't flexible with the time of day you travel and want to be able to ultimately choose the hotel you will stay at, avoid Priceline's Name Your Own Price service, which allows you to bid on flights, hotels and cars for deep discounts, but requires you to purchase the flight, hotel or car without knowing all the details up front. To compare hotel, airfare and car rentals on Priceline use the search field on the home page. Choose the Vacation tab if you want to search for packages--which is a good idea since they often provide the best deals. If your dates are flexible, try several different arrival and departure dates to see which days are cheapest. (Hint: this will usually be weekdays--Monday through Thursday.) Check the PriceBreakers page of the site for the best deals currently available. Check Southwest.com separately, as they are not included in Priceline's comparison searches.
If you are flexible with the hotel you stay at and the flight you take (that is, if you don't care about departure times or the number and/or length of layovers), then you may want to bid on your travel to get the best possible price. There are several things to keep in mind when using the Name Your Own Price feature on Priceline.
(1) With hotels, be particular about the areas where you are willing to stay and about the caliber of hotel you choose. Pay close attention to the detail map for each area in your destination city. Names of areas can be deceiving, and the Priceline zone designations sometimes change, so be sure to view the map before you commit to staying in a certain area. The same goes for the star rating of your hotel. With Priceline's Name Your Own Price, you are obligated to take the room/flight/car rental if you win your bid. With flights, keep in mind that when bidding, the only thing you are in control of is the departure and arrival airports, date and the flight.
(2) To figure out the average rate of a room in the area at the star level you have specified, use the Priceline hotel comparison search field on the home page and start your bid at 40% to 60% less than that.
(3) If you do not win your bid, you can bid the same bid 24 hours later or change your bid. Priceline may suggest that your bid is too low, but don't let this discourage you. Because the hotels themselves decide whether to accept or deny the bid, there is always a chance you'll get the low price you want.