DFW to ORD is always a hard commute, lots of commuters on that route. I often had to use FedEx to get to ORD from DFW (AFW-ORD direct non-stop) or drive down to ACT to do the ACT-IAH-ORD commute (when United Express flew the route - they don't anymore).
The Envoy New York base is a JFK co-domicile, and there's only one flight between DFW-JFK, the rest are DFW-LGA. so it depends on where your trip starts. It didn't seem too bad when I commuted DFW-LGA. Though EWR was always an backup if I couldn't get to LGA or JFK.
It's a matter of leaving yourself a lot of time for the commute. If you travel up the night before, you can always make it or two-leg the DFW-ORD through XNA, SGF, DSM, TUL, ICT, were a few of my options if I didn't drive south.