Key West, FL, USA to Chicago, IL, USA from $96: 5 ways by bus, train, flight or car
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How to Get from Key West to Chicago: Cheapest, Fastest and Best Way
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Traveling From Key West to Chicago
Journeying from Key West to Chicago brings you from the laid-back beaches and vibrant sunsets of Florida to the bustling city life and architectural marvels of the Midwest.
Best Neighbourhoods in Chicago
Chicago's neighborhoods each offer a distinct vibe and rich culture.
Best Times To Visit Chicago's Attractions
Timing your visits to Chicago's attractions can enhance your experience significantly.
Chicago Weather: What to Expect Year-Round
Chicago experiences a diverse climate with hot summers and cold, snowy winters, making each season distinct. Spring and fall are often regarded as the best times to visit, as mild temperatures enhance outdoor activities and sightseeing.
Dining Recommendation
Savor a deep-dish pizza at Lou Malnati's, where the rich, cheesy layers and chunky tomato sauce create a comforting, hearty experience unlike any seafood dish you enjoyed in Key West. The lively atmosphere and focus on local, fresh ingredients offer a vibrant contrast to the island's laid-back dining scene.
Key West - Chicago operators
Explore transport companies operating between Key West and Chicago, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.
Plane from Key West (EYW) to Chicago O'Hare (ORD)
Plane from Key West (EYW) to South Bend (SBN)
Plane from Key West (EYW) to Chicago O'Hare (ORD)
Plane from Key West (EYW) to Chicago O'Hare (ORD)
Plane from Key West (EYW) to Chicago Midway (MDW)
Plane from Key West (EYW) to Chicago Midway (MDW)
Bus from Key West to Downtown Miami
Bus from Miami FL to Chicago IL
Bus from Miami FL to Chicago IL
Drive from Key West to Chicago
Trips from Key West
- Key West to Marathon
- Key West to Sarasota
- Key West to Siesta Key
- Key West to Key Largo
- Key West to Homestead
- Key West to Cudjoe Key
- Key West to Naples
- Key West to Nassau
- Key West to Big Pine Key
- Key West to Islamorada
- Key West to West Palm Beach
- Key West to Duck Key
- Key West to Marco Island
- Key West to Miami
- Key West to Fort Myers
- Key West to Little Torch Key
- Key West to Atlanta
- Key West to Tallahassee
- Key West to Sugarloaf Key
- Key West to St. Augustine
- Key West to Seattle
- Key West to Cancun
- Key West to New Orleans
- Key West to Pensacola
- Key West to San Miguel de Cozumel
- Key West to Orlando
- Key West to Destin
- Key West to Panama City
- Key West to Southport
- Key West to Florida City
- Key West to Mexico City
- Key West to Cape Coral
- Key West to Boston
- Key West to Tampa
- Key West to Fort Lauderdale
- Key West to Havana
- Key West to Punta Gorda
- Key West to St. Pete Beach
- Key West to New York City
- Key West to Aruba
Trips to Chicago
- Fort Wayne to Chicago
- Nashville to Chicago
- Philadelphia to Chicago
- West Lafayette to Chicago
- Boston to Chicago
- Tampa to Chicago
- Milwaukee to Chicago
- New York City to Chicago
- Detroit to Chicago
- Minneapolis to Chicago
- Pittsburgh to Chicago
- Dallas to Chicago
- Kalamazoo to Chicago
- Cleveland to Chicago
- Ann Arbor to Chicago
- Omaha to Chicago
- Memphis to Chicago
- Kansas City to Chicago
- Las Vegas to Chicago
- East Lansing to Chicago
- Columbus to Chicago
- Denver to Chicago
- Los Angeles to Chicago
- Cincinnati to Chicago
- Naperville to Chicago
- Madison to Chicago
- Saint Louis to Chicago
- Champaign to Chicago
- Grand Rapids to Chicago
- Green Bay to Chicago
- Michigan City to Chicago
- Indianapolis to Chicago
- Bloomington to Chicago
- Peoria to Chicago
- Kankakee to Chicago
- Iowa City to Chicago
- South Bend to Chicago
- Toledo to Chicago
- Rockford to Chicago
- Cleveland to Chicago