Update and thanks. Completed the 500 mile trip w/o incident. Great advise on the winds - if they are coming from the south (blowing “up lake” from south to north) there will be stacked swells 4 - 5ft and if wind is over 10 knots, white caps on the swells. Good idea to hold up for a day or two and let the lake and wind calm.
We ran between 50 and 80 miles per day - Sturgeon to Manitowoc. Manitowoc to Milwaukee. Milwaukee to Chicago. Chicago down the ship and sanitation canal, Illinois river to the Mississippi. Ran our boat at about 1500 RPM using about 3.5 GPH per engine (8.3 Cummings). Average fuel price was about $6.00 and total cost was about $2,800. Marina cost was reasonable. Warning - marinas are VERY shallow south of Joliet - about 4 feet (maybe). Bridge heights in Chicago are at or higher (aka if 17ft, maybe 18) than advertised in Quemby’s (which is a great resource) along with the Great Lakes cruising guides.
The Brandon lock will let you through as soon as possible after 6:00 p.m. For those heading that way, recommend getting through Chicago early before tours start and parking on the wall at Joliet until the lock opens. Make plans to stay at a marina within your cruising distance before dark or have an anchorage selected. Best of luck to those who will likely do this in the fall.