Tough to do alot with a big group, especially with kids. They have a tendency to get tired. I'd do the aquarium one day, and the science and industry possibly the other. Boat tour is great for adults, but most kids won't be interested and it isn't cheap for the time. Lincoln Park Zoo is super nice and is Free. Big bonus there since you will be spending quite a bit at the other places. Also the lakefront is awesome.
If you want to spend weekend in Chicago, I suggest Shedd Aquarium, Architectural Boat Tour to Lake Michigan, Skydeck Chicago at Willis Tower or 360 Chicago observatory at John Hancock tower.. If someone of you don't fear heights.. Must go to Tilt at 360 Chicago.. If you go there, you can skip Chicago Skydeck. Also, dont forget to try Chicago Style Deep Dish Pizza... Can also visit Planetarium.. If you have kids with you.. Must check out Lincoln Park Zoo..
It depends on how long your family takes to go through museums. I definitely suggest shedd aquarium if youre going with the family.
You can do two But you still want see everything in two days at one . Yes and no
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