O'Hare International Airport (ORD) in January is a major hub for winter departures heading to warm destinations like Key West. Travelers should expect colder ground conditions, potential snow or ice delays, and higher-than-average demand for nonstop seats. Nearby major cities commonly accessing ORD include Chicago, Milwaukee, Indianapolis, Detroit and Minneapolis — useful for travelers considering alternate airports. To find the best January fares, monitor midweek departures, leverage fare alerts for ORD to Key West International Airport (EYW), and book early for nonstop options. CTA Blue Line, rideshares, and pre-booked shuttles remain reliable ground options; allow extra time for winter conditions. Book your Chicago to Key West flight today and check live ORD updates before travel.
Arriving at Key West International Airport (EYW) in January is ideal for travelers escaping winter. Expect comfortable temperatures, busy tourist areas, and a variety of ground transport options to Old Town (Duval Street), Mallory Square, and nearby islands. January is high season for Key West, so book transfers and rental cars in advance, and consider combined itineraries with Miami or Fort Lauderdale for international connections. Use location-based search terms like "Chicago to Key West flights" or "ORD to EYW January" to find the best deals and real-time arrival info. Ready to land in paradise? Book your Key West transfer now and secure January availability.
Starting from $313
Book your economy class flight from Chicago (ORD) to Key West (EYW)and save money on your travel. Compare all flight options to find the best deal for your january trip.
Starting from $379
Book your economy class flight from Chicago (ORD) to Key West (EYW)and save money on your travel. Compare all flight options to find the best deal for your january trip.
Planning a trip from Chicago (ORD) to Key West (EYW) in january? SlickTrip helps you find the cheapest economy class flights with our comprehensive flight comparison tool. Whether you prefer direct flights for convenience or multi-stop flights for savings, we have options for every budget and schedule.