I don't believe FL
ever served Canada, and with most of the cities in Canada you would think that WN
would serve being pre clear stations, they could fly just about anywhere in the US. You wonder though with the switch to Amadeus if they might try the WestJet codeshare again, or just try their own canadian service? There are some high landing fees though at many of those airports, so don't get your hopes up.
As for Mexico, MDW
does have an FIS so they could in theory fly just about anywhere in mexico from MDW
. Mexicana had some service at ORD
for a while, but with them belly up, there isn't much service outside of UA
in Chicago, and even that is limited at best. There is a hispanic population in Chicago though, so I think there would be enough to support some of the Mexican cities. SJU
is a stretch though and I am not sure that WN
's 737's would be able to get there from MDW
with the short runways.