Get up close and personal with airline consolidators such as Mobissimo, Kayak, Travel Zoo and other websites that post and compare fares on a daily basis and regularly offer intriguing package deals---especially to those who register for updates. Sign up for newsletters, emails and other communications.
Schedule your vacation for the offseason. Head to Cancun in the fall, after the kids are back to school and before rates hit Himalayan heights to capitalize on sojourners longing to spend year-end holidays lolling in the waters off Cancun. Sandwich your trip into a late spring time slot---after beer-chugging spring breakers head back to school, of course. Consider summer vacation dates that dance around major holidays. Expect sweet package deals during hurricane season, when only the bold dare to head south.
Bypass weekends and fly to and from Cancun in midweek, leaving on a Wednesday and returning on the following Tuesday, for example. Include a Saturday overnight to keep the price of your airfare down and expect to get reduced rates from hotels during the middle of the week as well as uber-cheap meals at restaurants.
Book a package in advance---before all of the discount airline seats disappear and hotel rooms fill. Expect full-fare packages to stay available longer than the cheaper ones, but if you're a gambler and love the thrill of seeing if you can snag a juicy last-minute deal, hang on until the last minute and hope that some of those full-fare accommodations go wanting so you can snatch them up.
Find major discounts by booking a Cancun package directly from well-known resorts such as Sandals and Couples. Establish yourself as a frequent stayer and your package cost might be further reduced. Look forward to adding an off-site excursion at one of these resorts by using cash you saved by booking directly from the host.
Check out SkyAuction. Thrill to deals that mix and match flights on major carriers with five-star hotels and plentiful amenities that could land you at the Royal Hideaway Playacar, Hacienda Tres Rios in Riviera Maya or Grand Oasis Cancun for $250 if nobody outbids against you. Find rock-bottom bidding in increments of $25, so even if you're not planning a Cancun trip now, you can practice your bidding skills for a future stay that might just redefine the word cheap.