Originally Posted by
Radio
You should apply right now, the process can be long.
I also jumpseat between Chicago and Anc, very easy commute and never had any problem. Ups doesn't have any direct flight, Atlas Air has. They are amazing to commute with. Airliners do stop the directs flights during winter.
Atlas and Polar both fly between ORD and ANC. They are the same company, but have two different certificates, so they have two different schedules and listings. CASS is good for both.