Cheap Flights from Orlando (ORL) to Chicago (CHI)
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Flight deals from Orlando to Chicago
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Find the cheapest month to fly from Orlando to Chicago
We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Orlando to Chicago flights are currently cheapest in May.Direct flights from Orlando to Chicago
Alternative Orlando to Chicago routes
Looking for the cheapest, fastest or easiest route from Orlando to Chicago? You could fly into the following airports instead.Orlando to Chicago: Flight information
The things to know before you go.Cheapest flight found | $49 |
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Cheapest month to fly | May |
Average flight time | 2 hrs, 51 mins |
Most popular airline | Southwest Airlines |
Average flights per week | 367 |
Finding cheap flights from Orlando to Chicago: Frequently asked questions
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.
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Prices shown on this page are estimated lowest prices only. Found in the last 45 days.