There is no direct water route across Lake Michigan from Holland, Michigan to Chicago, Illinois. The lake's geometry makes a straight-line crossing impractical for regular travel.
I-94/I-90 around the southern shore: ~125 miles, 2–2.5 hours. Crosses the Indiana Toll Road.
Lake Express High-Speed Ferry (Muskegon, MI ↔ Milwaukee, WI): 2.5 hours. Muskegon is ~25 miles north of Holland. Then drive Milwaukee→Chicago (~90 miles). Total: ~4 hours.
No commercial flights on this ultra-short route. General aviation possible but impractical.
Lake Michigan's southern basin is shallow, storm-prone, and heavily trafficked by commercial shipping. No passenger ferry operates the Holland↔Chicago corridor due to distance, weather unreliability, and insufficient demand versus the efficient highway alternative.