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Share your experience trying to search and book in the comments.
Right now there are incredibly cheap roundtrips to Cancun for Fall Travel, starting at $213 roundtrip. I see outstanding fares from Atlanta, Baltimore, Boston, Dallas, and Cleveland. There are probably other cities without outrageously good deals at the moment.
The two main places to search are ITA Matrix and southwest.com. Search both for your city. Search on ITA Matrix by calendar of lowest fares for acceptable trip lengths.
Baltimore to Cancun has $228 roundtrips.
Boston to Cancun has $365 roundtrips.
Dallas to Cancun has $278 roundtrips.
Cleveland to Cancun has $280 roundtrips.
The cheapest roundtrips I found were from Atlanta on direct flights. Southwest has $99 outbounds from September to December 2015.
Returns in the same months start at $115.
The total is $213, and you get two free checked bags both directions.
After searching on ITA Matrix and southwest.com, book with the cheapest carrier. Keep in mind what baggage fees are, especially if you book with Frontier and Spirit, which charge for carry ons.
Best Way to Buy the Ticket
Buy with the Citi Prestige® Card. The first $250 in flights per calendar year are refunded to you as a statement credit. This includes fees like the checked bag fee, seat reservation, or meals that you purchase at the time of ticketing or later. After the statement credit, your roundtrip ticket from Atlanta or Baltimore would be free.
If you’ve already maxed out the statement credit, you will still earn 3x ThankYou Points on the award taxes. The Citi Prestige® Card also comes with a 40,000 ThankYou Point sign up bonus.
Hat Tip Airfare Watchdog
Just getting started in the world of points and miles? The Chase Sapphire Preferred is the best card for you to start with.
With a bonus of 60,000 points after $4,000 spend in the first 3 months, 5x points on travel booked through the Chase Travel Portal and 3x points on restaurants, streaming services, and online groceries (excluding Target, Walmart, and wholesale clubs), this card truly cannot be beat for getting started!
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