Top 8 trips from Key West to Chicago

Key West to Chicago
starting from Key West
3.5 hours → Miami
4 hours → Ocala
4 hours → Valdosta
3.5 hours → Atlanta
4 hours → Nashville
3 hours → Louisville
2 hours → Indianapolis
3 hours → Chicago
24.5 hours of driving
Key West to Chicago via Orlando
starting from Key West
3.5 hours → Miami
3.5 hours → Orlando
4 hours → Valdosta
3.5 hours → Atlanta
4 hours → Nashville
3 hours → Louisville
2 hours → Indianapolis
3 hours → Chicago
25 hours of driving
Key West to Chicago via Lexington
starting from Key West
3.5 hours → Miami
3.5 hours → Orlando
4 hours → Valdosta
3.5 hours → Atlanta
6 hours → Lexington
2 hours → Indianapolis
3 hours → Chicago

25.5 hours of driving
Key West to Chicago via Montgomery
starting from Key West
3.5 hours → Miami
4 hours → Ocala
6.5 hours → Montgomery
4 hours → Nashville
3 hours → Louisville
2 hours → Indianapolis
3 hours → Chicago

26 hours of driving
Key West to Chicago via Naples
starting from Key West
5 hours → Naples
3 hours → Tarpon Springs
4 hours → Valdosta
3.5 hours → Atlanta
4 hours → Nashville
3 hours → Louisville
2 hours → Indianapolis
3 hours → Chicago
26.5 hours of driving
Key West to Chicago via Gatlinburg
starting from Key West
3.5 hours → Miami
3.5 hours → Orlando
1.5 hours → St Augustine
2.5 hours → Savannah
6 hours → Gatlinburg
3 hours → Louisville
2 hours → Indianapolis
3 hours → Chicago
26.5 hours of driving
Key West to Chicago via Memphis
starting from Key West
3.5 hours → Miami
5 hours → Gainesville
3.5 hours → Atlanta
2 hours → Birmingham
3.5 hours → Memphis
7 hours → Bloomington
2.5 hours → Chicago

28 hours of driving
Key West to Chicago via New Orleans
starting from Key West
3.5 hours → Coral Gables
3.5 hours → Orlando
4 hours → Tallahassee
6 hours → New Orleans
3.5 hours → Memphis
5 hours → Altamont
3.5 hours → Chicago

32 hours of driving

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Explore alternate routes from Key West to Chicago, or you can get reverse directions from Chicago to Key West. Don't forget to factor in the weather. You can check the road conditions from Key West to Chicago. Check out other stops like Orlando, Lexington, Montgomery, Naples (Florida), Gatlinburg, Memphis, or New Orleans. Try starting your trip from Duck Key, Little Torch Key, Marathon, Grassy Key, Key Colony Beach, Conch Key, Sugarloaf Key, Big Pine Key, or Little Torch Key. You can also change your destination to Arlington Heights (Illinois), Deerfield (Illinois), Elmhurst, Highland Park, Naperville, Oak Park (Illinois), Orland Park, Gary, or Evanston.