Upper midwest, the world is your oyster. People gravitate towards the bigger cities/coastal areas (myself included). I'd say it's never really too early to start your due diligence when contacting groups. Anytime CA2 year is a good head start on things. Get a nice CV together and research hospitals online. Make some phone calls and find out who the group president is and get his/her phone number or email address. You can generally get a lot of information on the hospital website and then doing a physician search for anesthesiology, most have a phone number that will get you some where. Then introduce yourself, state where you are in your training and that you're interested in the area. They'll usually have you send a CV in.
Right now you should make a short list of states you're interested in and research licensing requirements. They can vary widely. If they're a state that requires FCVS then start working on it now, it's very very slow and painful. Plan on 6 or more months for a license and credentialling at a hospital. If you work backwards you can do the math, you need to have a job contract signed by Jan/Feb your CA3 year to start in July. Some states are much easier to get a license (Indiana I've heard is 2 weeks, $200), but you should get some idea of what ones are a big hassle. The short list is Florida, Texas, California, Mass.
