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Take I90W to Portage, north of Madison. Take I39/US-51 north to Hurley.
Take US-2 east to Indianhead. 375 miles (approx. 6-8 hours)
Take I35 north to Duluth. Take US-2 east to Indianhead. 225 miles (approx. 4.5 hours)
Take I94 east to US-63(Baldwin). Take US-63 to US-2, west of Ashland. Take US-2 east to Indianhead. 225 miles (approx. 4.5 hours)
Take US-41 north to Oshkosh. Take 110 west to US-10, continue west to I39 Stevens Point. Take US-51 north to Hurley. Take US-2 east to Indianhead. 320 miles (approx. 5-7 hours)
Take I90 north to Portage. Take I39/US-51 north to Hurley. Take US-2 east to Indianhead. 285 miles (approx. 4-5 hours)
TakeĀ 29 to US-51, then US-2 east to Indianhead. (approx. 3.5 hours)