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I am from West Michigan (Grand Rapids Area). The winter drive can be hit or miss and depending what you plan on doing in Chicago the traffic can be difficult. From Boyne down to Chicago , you will have no issue as long as there is not a winter storm happening.
A tip if you want to avoid traffic:
I would drive down to New Buffalo and jump on a train if I wanted to visit Downtown Chicago. It's a bit slower but 100% stress free.
Best of luck on your travels.
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