Cheap Flights from Chicago to Orlando in 2019

Top last minute flight deals

Feeling spontaneous? It’s never too late to book a trip. Here’s our pick of the best last minute flights to Orlando...
Estimated lowest prices only. Found in the last 14 days.

Flight information Chicago to Orlando

Cheapest roundtrip price last month


Non-stop airlines


Flights per week


Average flight time, total distance 1002 miles

2h 30min

Most popular airline last month

Southwest Airlines

Orlando International and Orlando Sanford

2 airports

Frequently asked questions

There are 2 airports in Orlando: Orlando International and Orlando Sanford.
The best price found on Skyscanner for a flight from Chicago to Orlando is $75. This was found by aggregating across different carriers and is the cheapest price for the whole month.
2h 30min is the average flight time from Chicago to Orlando.
There are 6 airlines who fly non-stop from Chicago to Orlando.
There are 144 flights per week flying from Chicago to Orlando, as of October.

On your flight from Chicago to Orlando, you can fly out of either Chicago O’Hare, which is the busiest airport both in Chicago, and in the entire US, or Chicago Midway.  Your flight will arrive in Orlando International airport, which serves Orlando, Florida, and the surrounding area.  Average flight time between Chicago and Orlando is 2 hours and 40 minutes.  Directs flights connecting Chicago Midway to Orlando are carried on Southwest Airlines.  For travel between O’Hare and Orlando, flights are run by United, American, Frontier and Spirit airlines.

What to Expect in Chicago Airports

Whether you’re flying out of O’Hare or Midway, you can be sure that both airports aim at ensuring the most streamlined and comfortable travel possible.  Both airports allow passengers to be dropped off directly at the curbside of their terminal, but if you want to avoid potential traffic congestion, Chicago O’Hare also has a “Kiss ‘n Fly” drop-off location where you can be dropped off farther away from the airport traffic, and take a speedy shuttle provided by the airport directly to your terminal.  Both airports can also be reached by bus or train, and if you take those, you don’t have to worry about traffic or parking at all.

There are four terminals at Chicago O’Hare, but make sure to pay attention, because they are numbered 1, 2, 3 and 5 (there is no longer any terminal 4).  Your terminal and departure gate will depend on your airline carrier, so check with the airport website before your flight to ensure that you know where you need to be dropped off for check-in and departure.

Chicago Midway has a single open terminal which is divided into Concourses A, B, and C.  Flights from Southwest Airlines usually depart from Concourse B, but make sure to check with your airline and the airport website for the most updated information on your flight.

Regardless of whether you’re departing from to Chicago O’Hare or Midway, it’s recommended that you arrive 3 hours in advance of your flight to make sure that you have plenty of time to navigate check-in and security, and to find your gate without hassle.

Both airports provide not only a varied selection of restaurants and shopping spots for you to pass your time, but they also both feature yoga rooms where you can sit back, relax and stretch out before your flight in peace and quiet.  If you’re in Chicago O’Hare, you may also encounter some of their numerous public art exhibitions installed in the airport, or even the famous full-sized replica of a brachiosaurus skeleton.  The atrium, where you’ll find the yoga room also features an indoor garden, where many of the herbs and vegetables used in the airport restaurants are grown.

Arriving in Orlando

Orlando International Airport has an A and B side of the main terminal, and where you arrive will depend on your airline.  If you’re being picked up, you will want to let your party know which airline you’re flying with and your terminal side, so they know where to go.  Happily, the airport provides maps and instructions with gate and airline locations to make this process nice and clear.  You will also be able to catch a ride from a range of public transport options straight from the airport, even including cruise transfers in case you’re heading to Orlando for a luxury adventure at sea!  For more information, have a look at the airport’s transport information site, or check out Skyscanner’s information on Orlando, and car rental website, which will help you find the best deals.

What to expect: Time Zone and Climate

Orlando is one hour ahead of Chicago, since it’s in the Eastern Time Zone.  It has a hot and humid climate with only two major seasons, rather than Chicago’s four.  From April to September expect hot, muggy weather with high rainfall, and average highs ranging from 83 in April to 92 in July and August.  Unlike in Chicago, Orlando remains in the 90s in September and the mid-80s even in October.  The coolest months, December and January, still see highs in the low 70s, and lows from 49 to 50.  If you’re travelling in summer, be aware that Orlando is at relatively high risk during hurricane season, which technically lasts from June 1st to November 31st, although storms tend to be most likely in late summer.  For dryer weather, visit in October through April, when rainfall is considerably less.  In some years it is dry enough that the area suffers from wildfires, although the risk for these is relatively low until the later months of the dry season.  Keeping an eye on the news and checking weather conditions before you leave will help make sure that your trip to this popular destination is safe and enjoyable, as it is for the millions of tourists who flock to this beautiful location each year - in 2014 the city hosted over 63 million visitors!

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