I've done the Chicago Distance Classic the last 2 years and loved it. Are some really small hills once you get near the lakefront, around 7 1/2 miles in. But, depending on where you are from and how you train, hill size is all relative. I burst out laughing every year at the Minnie 15K when we get to the first "hill" on the road outside of the AK parking lot and people start yelling "HILL!!!" To me that is not a hill, it is a small and short incline
Oddest part for me in Chicago was running over the steel bridges and through the downtown buildings. I completely lose my GPS and don't recover it until mile 8. It is an odd race in that about the first half is big city streets and then you hit the lakefront running/bike path and it takes on a different feel. You have Lake Michigan on your right, the beautiful skyline to your left and you are running through a park. I must have taken 20 pics along the lakefront last year and still had my best half marathon time ever
I would highly recommend the Chicago Hilton. It is race headquarters and a short stroll to the start/finish. Also, if you are traveling with a friend, you can get rooms with 2 bathrooms for the same or only slightly more than a regular room.
Last year, I put in the hotel code from the Penguin' Race site and got the special race rate. The coolest part was that the 2 bed, 2 bath room was the same price as a single bath room when you had the code. I have done this race as a girls weekend with my sister, so having 2 bathrooms is really awesome
Note if you drive, parking is awfully expensive anywhere downtown. We have always flown in and taken the shuttle from the airport. Much more economical for us between the parking and now skyrocketing gas costs.
Don't know if we are going this year, but I have my fingers crossed.
Kathy