I follow the airline industry and here is where I think Southwest will fly in the beginning and why. They say 8-10 NON-stop flights daily to start.
Las Vegas - 2 non/stops I think. Vegas is a lock! Gamblers and excellent connections to west coast.
Phoenix - 1-2 non/stops. Popular destination and extra connections to Calif. SW will time these two city flights for 4 good connctions to Los Angles, Oakland etc. for example.
Orlando - 1-2 non/stops. They are starting in Dec. Disney will load planes.
Kansas City or St. Louis - 3 flights. Slightly more likely at KC. These flights are not only for those destinations, but to make connections to various cities in the network.
Midway - NO. Why you say. People drive from Milwaukee to Chicago, so the only reason you would fly there is for connections. The flight is just to short. Better to fly to St.L or KC where people from MKE will want to fly or connect. Beside since MKE is Chicago's 3rd airport they will want northern Chicago people to have a long distance flight option.
Other Florida destinations are possible(tampa) but maybe not the first set of destinations they pick.
Nashville - possible 1 daily flight. Destination underserved plus connections to east coast.
Baltimore - possible. They may want to fly to their big east coast operation and stick it to Airtran and their 3 daily non-stops.
Minneapolis - No. Better to use the planes on longer flights. Airtran is serving MSP with 3 new non-stops. That is the new competetion, use them instead. They will keep fares inline.
Texas non-stops. No. You will connect in ST.L or KC for those.
Keep in mind that Airtran is greatly expanding their MKE flights. 30 non-stops now(34 by June 11th) including LAX, San Fran., San Diego, Seattle, Baltimore, LGA, Boston, St.L and Washington National Starting June 11th. Airtran has set up MKE not only to serve that city, but make easy connections for people flying from the east and west coast. More effecient with flight times for them to connect at MKE than Atlanta. Airtran is an excellent discount airline. Even if you love SW sometimes Airtran may have a better option to consider. They are setting up a mini-hub in MKE. This has already helped pricing at MKE and with SW adding service it will only get better and cheaper.
SW and Airtran are not adding aircraft to there fleets now. They are only rerouting planes. So maybe SW won't expand as fast as you would like, but they are and will be a factor at MKE. Happy flying!
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