The World's Largest Triathlon with a Lake Michigan swim, Lake Shore Drive bike and Museum Campus run.
I did this race last year under perfect conditions (excluding the shock when i entered the water, as I am from South Florida) and to this day has been the pinnacle of my short triathlon journey. Great Race, Great City, and it got me excited to do races far far away. Knowing what great venues and races are out there, makes running, biking and swimming all the more easier.
I've done this race for the past 4 years and while it's a great race and city (I'm from Chicago), the ride on Lakeshore Drive is pretty awful with all the potholes-and much worse this year looks like than it was last year-I drive this road everyday to work. There tend to be numerous flats because of the bumps so be prepared-other than that-the run is great, though I think the course will have changed a little, they are doing construction on the sidewalk around the Shedd and the Adler Planetarium.
When I registered for this race in 2008 they only had the "Triple Challenge" spots left, so guess what I did?? 3 races in one weekend! haha, that was fun! It was great to get some pats on the back by the time the Olympic came around.
I wrote a review on the race and some things to look out for here:
Hope it helps you with your race!