Chicago mission does not work

But it does not work !!!!! You perform as indicated in the „Chicago mission“ and it does not count/ increase !!!!

Same - it does not count/ increase even if you perform times and times as indicated

I complete one mission and the second mission want start too

I competed the first of the missions, and now the second one isn’t registering any boat deliveries, extremely frustrating. 

I’m unable to open the Chicago Mission today. 

Same. Not going to bother from this point. It's looking pretty much impossible to get the gothic tower anyway, so why try?

I've done the first mission. Now, when I try to open chicago missions to se the next one the game just jumps back to the my town. I don't get any more missions.

I'm guessing shipments means airplanes not boats? 

"I'm guessing shipments means airplanes not boats?"

Boats only.

You have to tap the green button - "I'm on it" - to start the mission. 

The next missions show up as green clipboard in your capital city.