I'm taking the Amtrak Empire Builder to Seattle with a lot of luggage so I don't think that train would work. I'm actually starting my journey in Toronto, so I'll be crossing the border at the Blue Water and then passing through Landing before entering Indiana on I-94.
I've driven through Chicago before but never been into downtown. What I'm wondering is when I get to Lake Station if i should stay on I-94 and then get on 90 across the state line, thus avoiding tolls, or if I'm better off to take the Indiana Toll Road to the Skyway. Again this would be late morning or noon hour on a weekday. Cheers!