I'm normally a road racer and I've never attempted a 50K before, so this race was something totally different for me and I loved it. Lots of rolling hills on the course but nothing I was completely unprepared for (though training for hills in Chicago is quite a feat in itself) - the scenery definitely helped distract me from the pain :)

Pros:
+ Very scenic, even though it's not by the ocean/mountains. I really thought most of the race was beautiful
+ Really awesome volunteers make parking/aid stations/packet pickup a breeze
+ Lots of photographers on the course
+ Trail runs = super casual and fun atmosphere.
+ Aid stations every 5-6 miles with delicious snacks (chips, crackers, potatoes, skittles, m&ms, soda, Tailwind, water, broth, pb&j sammies, gu)
+ Delicious post-race meal & beer! BBQ sandwiches, fruit, potato salad, soup - all provided with entry!
+ Fire pits for pre-race (if it's cold) and post-race
+ Quick and easy start (all the racers crossed the start line within the first 2 minutes, no long wait to start or long waves)
+ Small enough race that the porta potty situation remains pretty clean & easy to access before the race start
+ Parking is only a couple of bucks for spectators and free for racers.
+ Not super technical. I did wear trail shoes (it seemed most people did) and there were some loose rock/sand/grasses/single track areas, but nothing too crazy.

Cons:
- A little tricky to navigate your way there, but once you get there it's a small enough race that it is very easy to figure out where to go/park.
- I really wish there were mile markers on the course. There are occasional flags and arrows throughout so I feel like mile markers would be easy enough to add in during set-up (I'm just salty because my Garmin was 2 MILES OFF! And finding out I had 3.8 miles to finish instead of 2 at the last aid station was heartbreaking)