I'm driving my 31ft cruiser from milwaukee to chicago..this would be my first trip of this sort...any advice???

do not hit the rock/sand bar in front of racine stay close to harbor to the right of the big green bouy or outside of big concrete structure with marker on it .and fill up with gas in wisconsin. waukegan harbor has sandwichs and icecream last stopping point going south till you get to chicago. have a nice trip

i figured about 79 nautical miles to hammond indiana...i have 2 75 gallon tanks this should be enough if i fill em up?

Milwaukee to Chicago - keep the shore starboard.
On the way back, port.

like mentioned,,if you fill up in wi it would save you some coin,,same for in,way cheaper their too...im surprised i-dot dont get you for taxing that also..