Answer: From Key West, Florida it is 2,218 miles, however other trip destinations like Pueblo, Colorado or Woodland Park, Colorado will require less driving. If square miles is what interests you, Denver covers about 155 square miles of area.
Answer: The driving distance between Chicago, IL and Denver, CO is approximately 1005 miles. The driving time would be approximately 15 hours 45 minutes 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, border crossings and rush hour traffic in urban areas.)