In this video I am showing you how to get all the notable awards from the Chicago category.

Timeline:
0:12 Pier Pressure (Drive a lap around the Water Park in Navy Pier in less than 50s)
1:16 Slapshot (Visit the Unified Arena hockey stadium between 7:00pm and 10:00pm, game time)
1:57 Radioactive (Drive 3.22 km around the Petroleum Plant in a green car)
3:42 Flights Delayed (Drive 402 km/h anywhere in Chicago Airport)

You will probably need to drive together with another crew member to get the Airport award because there is not enough space to get your car to 402 km/h without help. Thanks to s4nG for helping me out with it. You can visit his own channel here: [ Register or Signin to view external links. ]

Update: It is indeed possible to do it alone if you enter the airport on the south from the long street there. Doing it with a crew member will still be a lot easier though.

All the Chicago awards that are not shown in the video should be easy to understand but please don't hesitate to ask in the comments if you need help with some of those as well. I can explain how to get all of them.