Used to be MBS PremExec
Join Date: Sep 2000
Location: Saginaw, MI (MBS)
Programs: UA 1K 1.9MM, Marriott Titanium w/Lifetime Plat, Hilton LIfetime ♢, National Exec, Amex Plat
Posts: 5,722
If you pick a 757 to ORD, I'd say your chances are REALLY good. One of my coworkers is a Premier, and she is regularly upgraded on LAS-ORD-LAS. Sunday or Monday might hurt your chances, any other day of the week is probably pretty good outside of a major convention coming or going. About 6 months ago, the wife and I even flew into LAS on a Friday night and there were 2 empty seats in F on the 757. The upgrade list on the monitor had 3 people for 6 seats!
Although I'm a 1K, I've never missed an upgrade in/out of LAS. I think it is one of your easier upgrades if you can catch a 757.