Orlando to Chicago Flights: Find the Best Deals from MCO to ORD

First, arrive at MCO at least three hours before your flight during peak vacation seasons, as security lines can fluctuate significantly due to the high volume of families and tourists visiting the theme parks. Second, since Chicago weather is notoriously unpredictable, especially during the transition seasons of spring and fall, pack layers in your carry-on so you can adjust to the temperature drop immediately upon landing at O'Hare. Third, consider using the CTA Blue Line train for an affordable and reliable way to get from ORD to downtown Chicago, avoiding the often heavy and expensive highway traffic on the Kennedy Expressway. Finally, download your airline's mobile app before leaving Orlando to receive real-time gate changes and baggage claim information, which is vital in a massive, multi-terminal hub like O'Hare.

Flight prices between Orlando and Chicago often fluctuate based on the time of year and major events. Typically, the winter months—excluding the holiday peaks in late December—offer some of the lowest fares as the cold Chicago weather deters some leisure travelers. Conversely, prices tend to spike during the summer months when families are on vacation and during the spring break season in March. For the best value, consider booking your trip for mid-week departures in October or early November when the autumn foliage is beautiful and the crowds have thinned significantly.