Cheap Flights from Orlando to Chicago in 2019

Flight information Orlando to Chicago

Cheapest roundtrip price last month


Non-stop airlines


Flights per week


Average flight time, total distance 1002 miles

2h 40min

Most popular airline last month

Southwest Airlines

Chicago O'Hare International, Chicago Pal-Waukee, Chicago Dupage County, Chicago Midway and others

5 airports

Orlando To Chicago

If you're traveling from Orlando to Chicago, there are up to 165 flights per week from which to choose on this route. Catch direct flights from Orlando International Airport to either Chicago O'Hare or Midway Airports.

Getting Around Orlando International Airport

Orlando Airport consists of a main terminal that is divided into two separate main terminals, A and B. Terminal A connects to Airside 1 and Airside 2. Terminal B connects to Airsides 3 and 4.

You can stay overnight at a large hotel that is situated right inside the airport's main terminal, before security access, and avoid the chances of missing an early morning flight. This airport also has a walk-in medical service facility should you experience any health problems prior to your flight.

Southwest Airlines runs frequent non-stop flights from Orlando to Chicago. A direct flight to Chicago takes close to three hours. Depart your flight from Orlando to Chicago on Southwest at Airside 2 at Terminal A, which also serves Virgin America and AirTran. United and American Airlines also have frequent non-stop flights to Chicago, departing from Airside 3 at Terminal B and Airside 1 at Terminal A, respectively.

Chicago Airport Tips

Whether you take a flight from Orlando to Chicago landing at O'Hare or Midway Airport, you will find yourself within less than 20 miles of the Loop, Chicago's downtown district. Once you have claimed any bags checked, you can opt to rent a car at the airport and drive on to your hotel or other destination. Of course, you can also take public transportation or a taxi into downtown Chicago from either airport. If you arrive at O'Hare Airport and are in a rush to take a cab, there is a taxi stand at Terminal 2 that is often overlooked. Beat the crowds and head there instead of waiting in what can often be very long lines. You can also save time and money by taking the 24-hour CTA Blue Line to Clark and Lake for about $5.00, then grab a taxi from there to your location at a less expensive price.

When traveling on a domestic flight to Chicago, such as flights from Orlando to Chicago, you may want to use Midway Airport as opposed to the much busier O'Hare, which often has delays, especially in bad weather. Travel early in the day to avoid crowds and congestion.

Looking for hotels in Chicago?

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.