We are from the Green Bay area, so I hear you on flights from MKE. After 10 years of Christmas/NY travel (to MBJ and other caribbean islands annually), here is what I know:
1. Usually can get a charter flight from MKE, but you are bound to their travel dates. Usually a 7 day stint, with Sat-Sat service or Weds-Weds. As we usually go 10-14 days, this is not an option for us.
2. We have found direct from CHI (O'Hare), but not every year. I start looking in February when flights start to open, and truly check daily on matrix (site listed above), Kayak.com and direct websites like US Air.
3. This year, I found a one stop from CHI to MBJ on our way south, and a direct back from MBJ to CHI on US Air (so they do exist!!!). Decided not to book, as I really wanted to fly from MKE rather than drive to Chicago.....
4. We just booked our flight for this Christmas - flying from Milwaukee to MBJ. One stop, 1.5 hour layover. VERY reasonable for the holidays when I booked ($650/pp),
Good luck, happy hunting!
