We don’t do the MSP, ATL, or DTW legs, only the JFK legs. So you could have the jumpseat on those in your back pocket. DTW isnt bad out of ORD, tons of options on Delta (Skywest mostly) but other airlines too. MDW has the Southwest options as well as Delta out of DTW. Either way you slice it, driving to work is way better than commuting, however, a reasonable commute for better money is worth considering