I'm already signed up for the Chicago Tri Sprint distance but thinking about moving up to my first Olympic distance for my last race of the season. Two questions: Does anyone have insight into how late I can make that change? Could I make it at the end of June, after Leon's and PP? Secondly, any advice on Chicago vs. other races for a first effort at the Olympic distance? Thanks!
I found this on the registration FAQ page for how to make a change to your race entry: http://www.chicagotriathlon.com/registration/faqs/
Since they have a price change as late as 8/4, I'd guess that they would allow it they then (assuming Olympic distance is still open that late, which it was last year).
Hope that helps! If you want official confirmation, may be best to reach out to Tempe registration email on the FAQs page!