Hi, I had a really good experience flying Southwest Airlines O'Hare International Airport last month. I was anticipating the typical big-airport hassle, but Southwest has a really good operation here. The check-in was surprisingly fast, and the gate agents were friendly without being insincere – just nice people.
The ORD Southwest Terminal was tidy and there were sufficient outlets to plug in my phone, which is always a plus. Boarding was like clockwork, and they even had families and individuals requiring special assistance board ahead of time without hurrying them along – nice touches. The flight was boring (in the best sense), and we arrived on schedule. Honestly, it felt like Southwest brought some of its Midway charm over. If you’re wondering whether to fly them from here, I’d say go for it. No complaints from me!