I don't live in Chicago, but will be travelling to race...

http://www.chicagocriterium.us/

Your first concern should be finding a real pool.

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It hurts so bad, it feels good.

XXX is well supported and offer weekend rides to jump in. VisionQuest if you are willing to drop some money, but you also get use of their facilities, especially nice in the winter.

As for Masters teams, Chicago Blue Dolphins and Chicago Masters are probably most well known. Both have widely available practice schedules.

There are pools all over the place??

Q1, I don't regularly ride with either group but both have some really good riders, and some that are not so good, like any other club. I have latched on to the 2CC group ride that leaves from Evanston and goes North along Sheridan rd. a few times, and it's gone from a rather civil moderately paced ride to being a 30+ MPH hammerfest through the Northern burbs.

Q2, Check out either Chicago Blue Dolphins, http://www.chicagobluedolphins.com/ or The Chicago Masters http://www.chicagomasters.com/ The biggest difference between the two as far as I know it, is that the blue dolphins is a TI organization, and the Masters are not. Blue dolphins has a pay as you go punch card payment plan or monthly plan. The Masters have a monthly or quarterly system. The masters program you can show up and swim a few times to see if you like it/want to continue, the blue dolphins they ask that you fill out a form to come in for a "trial" swim. Both swim at UIC either LCM, or SCY depending on what UIC has going on. Personally I think that the Masters group has the better workout times.

As I understand it the blue dolphins have more of a structured workout each session, but I've never done a workout with them. The masters seem to be more of a come and go as you please the workout will be printed and stuck to a kickboard. If you have questions the coach will answer them, but I've never known them to proactively pull a new swimmer aside to "coach" them. The few times I swam with them the coaches were approachable but wouldn't stand over you to evaluate you or proactively coach.