I sold a boat on March 15 2002. The buyer insisted on a test drive which I didn't blame him , but it was damn cold! We went out on Spring Lake , Grand Haven port , but avoided Lake Michigan. It was 35 degrees and we saw 2 deer swimming across the lake!

Chicago area open water
 

The Cal Sag might be a good option. Some ice still exists but barge traffic keeps it thin. You can run up the river then.
Dress Warm!

When I had my fishing boat we would go out as soon as the ice left. You would see all kinds of stuff floating, even telephone poles and picknick tables. Be very carefull!

Agreed.
Those huge barge screws will bring just about anything up from the bottom!
This is not the area for poker run speed trials, just a good alternative for systems checks or test drives before The Lake conditions get better.
We kept a boat in a private harbor their for 3yrs. We were losing too much boating time waiting for the O'Brien Locks so we moved. If it wasn't for that, we probably would still be their.

petoskey lighthouse on march 1st taken from the lake

Hey, where is Oscar???

last week

Years ago I remember every spring some early fisherman would hit sunken ice on Lake Michigan near South Haven. You may never see the one that takes you under and there is little chance of survival before help arrives. If not ice, as others have mentioned, there is lots of Big floating debris.

he is standing next to me

I would wait until late april.