Submit feedbackComplete travel information for your December journey
In December, travelers can expect a mix of nonstop and one-stop flights from Chicago O'Hare International Airport (ORD) to Southwest Florida International Airport (RSW). Major carriers operating the route in winter include United Airlines, American Airlines, Southwest Airlines, and Spirit; frequency increases around holiday weekends, so book early for the best fares and nonstop seats.
A nonstop flight typically takes about 2 hours 45 minutes to 3 hours depending on winds and routing. If you have a connecting itinerary in December via hubs such as Charlotte (CLT), Atlanta (ATL), or Dallas/Fort Worth (DFW), plan for 5–7+ hours total door-to-door including layovers.
Yes — December holiday travel (mid-December through early January) typically drives up prices on ORD→RSW routes. Expect peak fares around Christmas and New Year's; booking 6–8 weeks in advance or monitoring fare alerts can help secure better prices for December travel.
Chicago O'Hare offers parking garages, economy lots, ride-share pickup points, and the CTA Blue Line for public transit even in winter months. During December, allow extra time for weather-related delays and heavier traffic; consider off-airport parking shuttles or pre-booked airport rides to reduce stress.
December in Chicago can bring snow and freezing temperatures that occasionally disrupt schedules at ORD. Airlines often issue alerts—check flight status before leaving, arrive earlier than usual, and sign up for airline text/email notifications to handle weather-related changes efficiently.
Passengers often use ORD when connecting to or from Chicago proper, Evanston, Naperville, Oak Park and even nearby Milwaukee for onward travel to Southwest Florida. ORD serves as a major Midwest hub for onward travel to Fort Myers, Naples, Sanibel Island and Cape Coral when flying into RSW.
December arrivals at Southwest Florida International Airport (RSW) are generally pleasant with mild to warm temperatures, averaging highs in the mid-70s°F (around 24°C). Holiday travel increases traffic, so allow time for baggage claim and rental car lines, and expect seasonal airport staff increases to handle crowds.
Yes — RSW offers rental cars, shuttle services, rideshare pickup, and regional bus connections to Fort Myers, Naples, Sanibel, Cape Coral, and Bonita Springs. Because December is a popular travel month, pre-book shuttles or rental cars to secure preferred pickup times and rates.
For domestic flights from Chicago O'Hare (ORD) to RSW, standard domestic baggage claim procedures apply — collect checked luggage at the baggage carousel and follow posted signs to ground transport. December holiday crowds can slow baggage delivery, so report delayed baggage promptly and keep receipts for expedited handling.
As of December, standard TSA and airport health guidance applies; check RSW's official site and your airline for the most current health advisories. Many travelers find that routine safety measures remain in place; however, specific local restrictions may change, so confirm before travel.
December activities near this route are attractive to travelers: Chicago hosts the Christkindlmarket, Millennium Park ice skating, and extensive holiday dining, while Southwest Florida offers the Edison & Ford Winter Estates holiday lights in Fort Myers, Naples Zoo Lights, Sanibel and Captiva island holiday markets, and New Year's Eve beach gatherings. These seasonal events drive travel demand on ORD→RSW in December and are useful context for marketing keywords like "Fort Myers holiday events" and "Chicago to Naples December festivities."
The best time to fly from Chicago O'Hare International Airport (ORD) to Southwest Florida International Airport (RSW) depends on whether you prioritize price, weather or convenience. For the lowest fares in December, aim for early December weekdays (Tues–Thurs) outside the Christmas/New Year peak. For warm-weather escapes, late-December offers sunny beach days though prices rise; for quieter beaches and lower hotel rates, target early December. Use searches with "flexible dates" to surface the best seasonal fares.
Choosing between direct/nonstop and connecting flights on the ORD→RSW route hinges on trade-offs: nonstop flights save time (approx. 2:45–3:00) and reduce baggage/connection risk, while connecting itineraries can be cheaper and offer more schedule flexibility. Common connectors for ORD→RSW include ATL, CLT, DFW, and MSP. In December, consider a nonstop for holiday travel reliability; for off-peak savings, check one-stop options.
Major carriers operating ORD→RSW in December include American Airlines, United Airlines, Southwest Airlines, and Spirit Airlines. American often offers competitive nonstop and one-stop options with a balance of schedules; United provides good timing for business travelers from ORD; Southwest can have lower base fares and free checked bags for two pieces, and Spirit is typically cheapest but charges for baggage and seat assignments. Compare total trip cost (fares + bags + seat fees) rather than base fare alone for December bookings.
December travel between Chicago O'Hare International Airport (ORD) and Southwest Florida International Airport (RSW) requires planning for cold departures and warm arrivals. Pack layered clothing and sunscreen, check winter-weather alerts for ORD, and pre-book airport parking or rideshares. For holiday travelers, carry proof of vaccination or masks only if required by specific carriers or venues, and always keep important documents and medications in carry-on luggage. Use CTAs such as "Book your nonstop ORD to RSW December flight now" and "Sign up for fare alerts to save on Chicago to Fort Myers December travel."
Typical nonstop flight time from Chicago O'Hare International Airport (ORD) to Southwest Florida International Airport (RSW) is approximately 2 hours 45 minutes to 3 hours. Schedules in December generally include morning, midday and evening departures; frequency rises near holidays. Key carriers offering nonstop or direct flights on this route include American Airlines, United Airlines, Southwest Airlines, and Spirit Airlines, with connecting options through Atlanta (ATL), Charlotte (CLT), Dallas/Fort Worth (DFW), and Philadelphia (PHL).
Finding cheap flights from Chicago O'Hare International Airport (ORD) to Southwest Florida International Airport (RSW) in December requires flexibility and timing. Primary strategies include booking mid-week departures (Tuesday–Thursday), setting fare alerts for flash sales, and comparing nonstop vs. one-stop itineraries. Use keywords like "cheap ORD to RSW flights December", "last-minute Fort Myers deals", and "holiday flight discounts Chicago to RSW" in meta content. Consider low-cost carriers or early-morning flights for reduced fares, and clear browser cookies or use incognito when checking rates. For group travel or snowbird stays, look for multi-city or extended-stay discounts.
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From RSW you can quickly access Fort Myers, Naples, Sanibel Island, Cape Coral and Bonita Springs — all popular December getaway spots. Visitor services at the airport offer connections and tourism information for these nearby beach and cultural destinations.
RSW sees spikes around mid-December, the week of Christmas, and New Year's Eve; flights and rental cars can fill up early. If traveling to holiday events in Fort Myers, Naples, or Sanibel, book accommodations and airport transfers well in advance to avoid sold-out situations.
