I had the opportunity to run the Chicago Marathon as a member of the Nike Pace Team. Chicago is the second biggest marathon so I wanted to check it off the list either way. It didn't disappoint. The city is amazing and the crowd energy is Epic! I stayed at the Westin on Michigan Ave which is about a Mile away from Grant park where the race begins and ends. Great walk to and from the race. The expo is further, so public transit is a must, or via Uber. To and from airport by way of the L Train. I would highly recommend doing Chicago at least once. You won't be disappointed.
Pros:
- Beautiful City
- Flat Course for fast running
- Sponsored by NIKE (Nike Pace teams available)
- Crowd energy is amazing, Lots of scenery along the course
- Aid stations and medical staff at every turn

Cons:
- Parking (foget'abow'it)
- Buildings downtown create a wind tunnel, you can get slammed by unexpected gusts
- Metal grates on bridges are not ideal to run on
- So many people that you are crowded in at times (but always have someone to run with)