Cheap Flights from Chicago (CHI) to Orlando (ORL)

Top tips for finding a cheap flight from Chicago to Orlando

Finding cheap tickets from Chicago to Orlando is easy with a little flexibility. Use our Whole Month search feature to scan through the calendar for the cheapest dates. You can also set up a Price Alert for your route and let us monitor the fares for you, sending notifications when prices change. If you’d rather skip layovers, select the Direct Flights search to view non-stop options that’ll save you time.

Booking your tickets early often leads to savings, but we can also find you some last-minute deals. In general, December is the best time to schedule your trip from Chicago to Orlando, with the lowest average fares across the board. Keep these strategies in mind to find the best itinerary.

Handy information about Chicago airport

Chicago caters to a broad range of air travel needs through its diverse array of airports. Chicago O'Hare International Airport, one of the world's largest airports, boasts four terminals, providing numerous ground transport options including the CTA "L" train, connecting passengers to virtually anywhere in the city. It serves a wide range of domestic and international destinations, with a dedicated terminal for international travelers.

Complementing O'Hare, Chicago Midway International Airport operates from one terminal with three concourses and ensures connectivity with various ground transportation modes, focusing primarily on domestic flights and a few international routes. For more personalized travel, both Chicago Executive and DuPage Airports offer a terminal each for private and corporate aircraft, alongside convenient transport services. Lastly, Chicago Rockford, despite its single terminal structure, supports domestic travel, particularly catering to budget-conscious passengers. Each airport, strategically located, makes accessible the vast metropolitan landscape and aligns with different travel preferences, maintaining Chicago's reputation as a significant transportation hub.

Orlando airport: good to know

Orlando serves as a gateway for many travelers with its two main airports: Orlando International Airport and Orlando Sanford International Airport. Orlando International Airport features two terminals, Terminal A and Terminal B, both offering domestic and international flights. A shuttle service connects each terminal to the main Landside Terminal, with pedestrian walkways also available for transit. Orlando Sanford International Airport operates from a single terminal, handling both domestic and international flights, and offers passengers the convenience of direct access from the adjacent parking area. Plan your flight from Chicago to Orlando ahead of time for a stress-free trip.

Best time to fly from Chicago to Orlando

The best time to fly from Chicago to Orlando is from December to February when Orlando offers a respite with its mild winter temperatures, averaging between 50°F and 72°F. This period avoids the heat and humidity you'd encounter during the summer months, ensuring more comfortable exploration and outdoor activities. Despite the possibility of cooler spells, the weather is generally warm enough to enjoy all that Orlando has to offer without the intense summer rainfall.

Reasons to visit Orlando

When planning your trip to Orlando, check out these activities and attractions Orlando has to offer. Engage in the cultural delight that is the Epcot International Food & Wine Festival, where culinary artistry and global cuisine meet in a spectacular celebration of gastronomy. Spend a day exploring Walt Disney World Resort, a world-renowned park where fantasy becomes reality across vast realms of adventure and wonder. Thrill seekers and film enthusiasts can immerse themselves in the action at Universal Orlando Resort, offering immersive experiences and entertainment inspired by blockbuster films and television series. For a more serene experience, connect with marine life at Discovery Cove, where you can swim with dolphins, snorkel among tropical fish, and savor a slice of paradise.

Add hotel bookings and car hire to your Chicago to Orlando flight

Planning your trip to Orlando is easy and convenient with Skyscanner. Select from trusted car rental providers like Alamo, Hertz, and Thrifty to navigate the city at your own pace. Accommodation choices include "Universal's Cabana Bay Beach Resort" for its proximity to the parks, "Hyatt Regency Orlando" for its central location, or "Floridays Resort Orlando" for a home-away-from-home experience. With Skyscanner, you have the freedom to choose options that suit your itinerary and budget preferences.