Flight Deals from Chicago O Hare Airport to Orlando International Airport from $84

Peak prices from Chicago to Orlando occur in late March to early April, while the lowest fares are found in mid-September.

When planning your flights from Chicago to Orlando, consider that the most expensive times typically fall between late March and early April, where prices peak around $289. Conversely, one of the lowest price periods is mid-September, with fares dropping to around $153. Generally, the high season is concentrated from mid-March to late April and late May through early July, with price variations of about $60 to $100 compared to the low season, which is in early January and September. The seasonal transitions are abrupt, especially from mid-March to late March.

Book from 25 to 36 days before departure to secure the lowest prices for your Chicago to Orlando trip.

For your trip from Chicago to Orlando, the best time to buy tickets is between 25 to 36 days before departure, with the most affordable prices seen around 33 days prior, typically ranging from $197. Booking earlier than this can lead to significantly higher costs, up to $325, which is a 65% increase. Prices remain reasonably low until about 15 days before departure but become volatile and ultimately increase rapidly from $200 to as high as $402 as the departure date approaches. Therefore, it's advisable to purchase your tickets well in advance to avoid higher prices.