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The driving distance between Madison, WI and Chicago, IL is approximately 149 miles. The driving time would be approximately 3 hours if you were to travel non-stop in good driving conditions. (The driving time does not take into consideration conditions which may extend trip time such as weather, road work and rush hour traffic in urban areas.)

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The driving distance between Madison, WI and Chicago, IL is approximately 150 miles. The driving time would be approximately 3 hours if you were to travel non-stop in good driving conditions. (The driving time does not take into consideration conditions which may extend trip time such as weather, road work and rush hour traffic in urban areas.)