Super cheap getaways to the Caribbean via AA Economy Web Specials

American Airlines is continuing to run unadvertised Economy Web Specials (which first debuted in November 2018).  This time, they have outstanding economy award prices to a few warm weather destinations.  The most notable for the ability to escape winter’s cold death grip is Chicago to Montego Bay for only 10K miles each way.  More importantly, award availability is wide open throughout the cold winter monthsThe Points Guy reports the following Economy Web Special routes, but there may be many others (If you find other routes, please let us know so we can update this post!):

  • Chicago (ORD) to Montego Bay (MBJ) for 10K miles one-way
  • Miami (MIA) to Aruba (AUA) for 5K miles one-way
  • Miami (MIA) to Belize (BZE) for 5K miles one-way

Economy Web Specials on Click the box:

If Economy Web Specials are available for the route you search, a box labelled “Economy Web Special” will appear. doesn’t always show those rates by default.  Instead, make sure to click:

Wide open awards

AA award space is often extremely difficult to find, but in the case of flights from Chicago to Montego Bay, and back, economy awards are wide open for at least 2 adults:

About Greg The Frequent Miler

Greg is the owner, founder, and primary author of the Frequent Miler. He earns millions of points and miles each year, mostly without flying, and dedicates this blog to teaching others how to do the same.

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Boy is that cheap and available too. Yes you show us the Deals !


Up to 15k now or 30k rt Ord..


found PHL. to AUB 7,500 March 26th