Hijacking small town public access channels was fairly easy. Taking over the feed for two different stations in Chicago is a whole different level. The basic hack is the same, but "just scale it up" isn't trivial in this case.
People used chained TV reception amplifiers to broadcast pirate TV :)
I'd guess that interfering with a digital TV signal today is considerably harder than an old analogue TV signal.
Broadcasting DVB-T is pretty trivial and people have even done it with a raspberry pi and a piece of wire (in an awful distortion-creating way) but getting people to tune to it will be harder. Also the power amplifier bit would be tougher but doable.
In fact since the days of SDR you can broadcast almost anything. You can run your own 4G mobile base station with one of those.