I do the MDW commute from a midwest USA city serviced by SWA. I will say that it is harder than I imagined. Flights frequently fill up and I have missed 1 report in 1.5 years here. That also being said I did tally up the numbers for this year so far and I have spent an additional 31 days away from home because of commutting. Not only do I miss out on significant monetary value but also time at home. Also being a summer 2017 hire it took me 4 months to get to MDW but some are able to pick it up as new hires. YRMV. Good luck