Suggestions on good starter race for friend - Chicago
I've heard good things about Lake Mills (between Milwaukee and Madison) which is run the first weekend in June.
High Cliff, near Appleton, is a very nice Sprint in late June (they also run a half-iron the same day). Bike leg is long for a Sprint--20 miles. Both the bike and the run on the Sprint course have 1 tough hill at the start but are generally easy after that.
Just curious....why are you wanting it to be large? When I did my first tri, I very much wanted to find one that was smaller in size. Those Danskin races sound like a big zoo to me still! Didn't want my first experience to be getting pummeled in the swim, or having to constantly navigate around a million bikes.
I'm in WI, so don't know many races in Chicago. Lake Mills, mentioned above, is a good 1st tri. But, I know there are a ton around Chicago closer to home for you.
Pleasant Prairie has a very nice Oly. (Aug)
http://www.pleasantprairietriathlon.com/
Spirit of racine has both a sprint and a HIM. (Jul)
http://www.spiritofracinetri.com/index.php
RV
It takes a long time to get good. - Scott Molina
Slow is smooth; smooth is fast. - Rich Strauss
Lake Mills is good, Also the Big Foot Tri, TDS Pewaukee Tri, Camp Whitcomb/Mason, are all good. The Rockton or Freeport Tri's in IL are nice cheap low key ones with pool swims... It seems like at the Chicago tri there is a higher than usual concentration of beginners even though it is a big race...
I think of all those, the Big Foot Tri is my favorite (http://www.customcompetitions.com)


I have a coworker who is seriously considering starting to do triathlons. He was a competitive swimmer in high school and is now starting to run again.
What would be a good race to try to get him to target? We are near Chicago. I am a transplant, and the only local races I have done are the Chicago Triathlon and the Milwaukee Xterra Championships. Those are pretty far off, so I am looking for an early season sprint. It should be something well organized and reasonably large.