If you are really from NYC, you have an advantage you can decide whether or not you choose to use.
First, if you don't mind the tolls, just run I-80/90 to I-94 about Gary/Chicago. That is simplest. As a refugee from that same megopolis, I can tell you that Chicago traffic will not be more than you can handle.
If you don't want to deal with Chicago, running I-94 out to I-39 to go north works well, and we do that if we are at a bad time for Chicago traffic.
This is not we would do (have done) because we avoid tolls (tolls - too many wheels).
Matt