hello all, I am new to this forum.
My family is in Cincinnati, and I got a job offer in Chicago, so I need to fly home every Friday night, and back to Chicago Sunday night or Monday morning.

I heard from friend's friend who joined Booth MBA that he had a deal with one of the airlines, and got very cheap flight every week. I am still trying to get more information from this friend, meanwhile want to hear options from you all.

any input is appreciated!

Don't know much about them myself but AirPass and PassPlus (AA and UA respectively) are mentioned frequently on these boards for this type of thing.

I think AirPass is more accessible for individuals while PassPlus is more geared towards small to medium size businesses (higher minimum spend requirements).

Thank you very much @duke787, it's very helpful! I will check both options!!!^

Are you working in a part of Chicago and living in a part of Cincy where flying is actually worthwhile? For me, something like this might come down to whether I was working downtown vs. somewhere near ORD. Could also depend in which side of Cincinnati I lived on, although I know less about that bit...

Midway doesn't appear to be an option (to CVG, anyway).

My guess is that fare-watching and just booking the best rates is *probably* going to beat AAirpass. Being predictable Fri-Sun, you could jump on a fare sale and buy 5-10 trips at a time.

Since you're doing this repeatedly I wouldn't advise the hidden-city trick that I imagine most Cincinnati people are well aware of. The fly-to-Indy-instead idea is kind of pointless unless your job is pretty much *at* ORD...

No idea whether the student discount idea is still a thing...or how closely it's limited to current students. (I remember using student fares in Europe in the 1990's but rarely see it talked about in a current domestic U.S. context.)

When I was a student in Chicago, I didn't take my car, and I generally flew back as Amtrak is garbage and the bus is hit or miss. I was there from 2009-2011, United did special Friday night departure Sunday return deals, generally sometime early in the week, starting Maybe Monday and ending Thursday morning, United deeply discounted most of their Friday evening flights from ORD that were geared more towards regional business destinations, and they required a Saturday night stay. AA and Delta would often follow suit, picked up a few tickets for $60 or so. Otherwise, at that time the standard fair was usually about $450.

I will be taking the Chi-CVG-Chi route again as apart of winter travels in January, and the Southwest effect is real, picked up a one way on AA from ORD to CVG for like $40 and I picked up a return to Chicago on WN for like $50.