The only reason the Autobots were able to get as far as they did was because of the ELEMENT OF FUCKING SURPRISE! Chicago was the fortified position. That's why they immediately get shot at when they try to enter, and no aircraft can get any intel. It's pointless because like in the above response the Decpeticons are shown to be prepared for a major attack. So what, that didn't win the battle. No, they didn't. You seem to be forgetting that Blackout was being hammered by the F-22s. You know, AIR SUPPORT! You can't paratroop in if the Decepticons shoot down your planes. They were lucky they had the wing suits. Yeah, so what?