Milwaukee is a smaller airport and sometimes is cheaper than O'hare. Funny thing is I have flown out of Milwaukee paid a few 100 less than had to hop to O'hare and than fly out of the same flight I just saved $ on.
I think Milwaukee is easier as it is a straight shot to the base and less tolls.
I have flown through both O'Hare and Milwaukee, and found Milwaukee the easier airport to use. It is smaller, easier to navigate, and the drive is much nicer. It is about the same distance.
Like Angie, I found cheaper fares to Milwaukee, by $100 to $150 less than O'Hare.
I flew into Milwaukee as well. Cheaper and smaller. We rented a car and drove to to the hotel in Waukegan. Didn't take too long.
Flew into O Hare just this week. It was crazy!
Do you remember How long the drive was from Milwaukee to Waukegan. My Husband and I never fly so I'm thinking going to Milwaukee would be better.