So I'm looking into possibly going back to part 121 once my training contract for my 135 gig expires or at least pro-rates down to point where I can pay it off. Likely Jan/Feb of 2019

My question here is, where to go?

I'm 37, I live just outside Chicago (so ORD/MDW ideal bases)
Masters Degree
I have 3500 hours total
900 Turbine (all jet)
150 PIC Turbine
and around 160 hours of 121 time from years ago.
No accidents, incidents, no failed checkrides, no DUIs or other disqualifying factors.

So to ideally stay in Chicago, or at least get back here from a short stint commuting, what is my best option? Envoy? Republic? Other?

Don't quite have enough time for the LCCs, but being 37 I don't want to be stuck either.

I've got CJO from RAH and SkyWest and ideally want to hold ORD soon after training, I'm trying to make my decision now as well. I think your decision will be based be based on several options including: do you care with airframe you fly, how much are you wanting to fly, is upgrading quickly a goal, QOL considerations (you are already living on base at ORD sounds like).

SW ORD CRJ- ORD is very junior on CRJ FO and CA side. From what I've been told could hold ORD right out of training on CRJ, reserves would be minimal, and you would fly a lot. QOL may be less, but upgrade times quick (12-18 months).

SW ORD ERJ- Most junior FO 8/16/18 , Jr CA 10/01/2015 Still pretty JR, I've heard expect LGA first but you could transfer fairly quickly. Could sit reserve longer (5-6 months), not sure if you would block less time in ERJ vs CRJ (if that matters to you). Upgrades are 2.5-3 years.

RAH (all ERJ)- ORD you could hold as FO within probably six months of training. Most junior there is 6/25/2018. But CA is different story at RAH. ORD is the most senior and we're talking like 10 years.

If you dont care about airplane- On CRJ class date is fast , reserve less, lots of flying, upgrade quickly.

Other considerations: RAH training is backed up more than they are telling people, pay is equal now first year with the SW new TA. RAH has 17,500 signing bonus SW has zero, RAH is union with slightly better contract (IMO) than SW, but I think pilots are happy at both places overall. end of day they are both regional.

I completely forgot about SW. RAH and SW both don't have any flow agreements, Envoy does, but Envoy I've heard has a terrible QOL

I hear you on the flow agreement, but Flow is at least at 7 years or more currently, Envoy is a very disorganized company, and it seems to have some QOL issues. If you want AA eventually, maybe a consideration, but with your time if you choose a regional where you fly often, build time, upgrade, and have good QOL all the while, that would be hard to beat and hopefully you aren't waiting 7 years to move. Keep you airline apps updated and shop yourself, dont just get lazy and wait for flow. If there were an economic downturn and you got stuck, RAH has the best QOL and Skywest is a huge company that has been around for a long time, and most of SW pilots seems to be happy. You'll have good QOL living on base as well. You could hold ORD as FO and CA with SW as well on CRJ.... Just food for thought. Tough decision as I am going thru it right now and time to decide..

For someone who lives where you do and wants to move in quickly the CRJ at Skywest is a slam dunk. If you need the FO bonus and don't mind a year or two more at the regional level, nothing wrong with Republic. Seems like your call.

The fact that Envoy is hiring DECs ought to warn you about them but to each his own poison.

Are they still doing the $7500 bonus for guys with a turbojet type rating and 135 experience?

Yes.

Filler

Skywest? So they say...

"SkyWest is currently offering a $7500 bonus for those currently flying for a FAA Part 135 or has a type rating in a turbo jet aircraft > 12,500lbs. To be paid out upon completion of IOE."

But I'd verify the specifics with a recruiter and get it from then in writing, if you are interested.

For a current- RJ rated pilot.......

I've got types in a Hawker, Lear 35/55, and Lear 45/75 as well as an SIC type in a ERJ-145