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Cheap flights from Chicago to Orlando International

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Compare Chicago to Orlando International flight deals

Find the cheapest month or even day of the year to fly to Orlando International

Book the best Orlando International fare with no extra fees

Flight deals from Chicago to Orlando International

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to Orlando International? Find the lowest prices on one-way and round-trip tickets right here.
Orlando.C$108 per passenger.Departing Sat, May 10, returning Sat, May 17.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Chicago O'Hare International on Sat, May 10, arriving in Orlando International.Inbound direct flight with Frontier Airlines departing from Orlando International on Sat, May 17, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$108, select.
Orlando.C$135 per passenger.Departing Sat, May 31, returning Tue, Jun 3.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Chicago O'Hare International on Sat, May 31, arriving in Orlando International.Inbound direct flight with Frontier Airlines departing from Orlando International on Tue, Jun 3, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$135, select.
Orlando.C$136 per passenger.Departing Wed, Jun 4, returning Sat, Jun 7.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Chicago O'Hare International on Wed, Jun 4, arriving in Orlando International.Inbound direct flight with Frontier Airlines departing from Orlando International on Sat, Jun 7, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$136, select.
Orlando.C$170 per passenger.Departing Sat, Jul 12, returning Tue, Jul 15.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Chicago Midway on Sat, Jul 12, arriving in Orlando International.Inbound direct flight with Frontier Airlines departing from Orlando International on Tue, Jul 15, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$170, select.
Orlando.C$173 per passenger.Departing Mon, Apr 28, returning Fri, May 2.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Chicago Midway on Mon, Apr 28, arriving in Orlando International.Inbound direct flight with Frontier Airlines departing from Orlando International on Fri, May 2, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$173, select.
Orlando.C$177 per passenger.Departing Fri, May 16, returning Fri, Aug 1.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Chicago O'Hare International on Fri, May 16, arriving in Orlando International.Inbound direct flight with Frontier Airlines departing from Orlando International on Fri, Aug 1, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$177, select.
Orlando.C$177 per passenger.Departing Mon, Jun 2, returning Sat, Aug 2.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Chicago O'Hare International on Mon, Jun 2, arriving in Orlando International.Inbound direct flight with Frontier Airlines departing from Orlando International on Sat, Aug 2, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$177, select.
Orlando.C$178 per passenger.Departing Mon, Jun 30, returning Sat, Jul 5.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Chicago Midway on Mon, Jun 30, arriving in Orlando International.Inbound direct flight with Frontier Airlines departing from Orlando International on Sat, Jul 5, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$178, select.

When is the cheapest time to fly from Chicago to Orlando International?

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Orlando International flights are currently cheapest in May.
Apr
from C$297
May
from C$108
Jun
from C$136
Jul
from C$170
Aug
from C$188
Sep
from C$199
Oct
from C$199
Nov
from C$201
Dec
from C$548
Jan
from C$548
Feb
from C$548
Mar
from C$553

Direct flights from Chicago to Orlando International

Chicago to Orlando International: Alternative routes

Compare routes from Chicago to Orlando below. You may find an airport to fly into that's cheaper, faster, or easier than Orlando International.

Chicago to Orlando: Flight information

The things to know before you go.
Cheapest flight foundC$108
Cheapest month to flyMay
Average flight time2 hrs, 43 mins
Most popular airlineSouthwest Airlines
Average flights per week988

Finding cheap flights from Chicago to Orlando International: Frequently asked questions

The best price we found for a round-trip flight from Chicago to Orlando International is C$108. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 43 minutes is the average flight time from Chicago to Orlando International.
Southwest Airlines, American Airlines and Alaska Airlines fly direct from Chicago to Orlando International.
There are 494 flights per week flying from Chicago to Orlando International, as of April 2025.
The cheapest month to fly from Chicago to Orlando International is usually April 2025.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Orlando International Airport on Saturday, May 10, 2025.
Yes – the average flight time is 2 hours and 43 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Orlando International but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Orlando is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Orlando International is Frontier Airlines.

How to find cheap flights to Orlando International from Chicago

Looking for cheap tickets from Chicago to Orlando International? Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

  • Simply hit "search." From Delta Air Lines to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from Chicago to Orlando International. And with us, there are no hidden fees – what you see is what you pay.
  • Compare flight deals to Orlando International from Chicago from over 1,000 providers. Then choose the cheapest plane tickets or fastest journeys.
  • Flex your dates to find the best Chicago–Orlando International ticket prices. If you're flexible when it comes to your travel dates, use Skyscanner's "Whole month" tool to find the cheapest month, and even day to fly to Orlando International from Chicago.
  • Set up a Price Alert. You can easily track the fare of your cheap Chicago–Orlando International flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
  • Fly without stops. Only interested in direct flights between Chicago and Orlando International? Make sure to tick "Direct flights only" when performing a search. If there are direct flights available on the route, these will appear in the results.
  • Find the cheapest Business Class flights from Chicago and Orlando International. We scour the Internet for the best Business, Premium Economy and First Class flight fares to Orlando International, too. Check the difference in price as you search – you might just stumble on a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
  • Include nearby airports in your search. Widen your search for Chicago to Orlando International flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save the next time you travel.

    • Combine your flight to Orlando International from Chicago with hotels and car rental

    Once you've secured your cheap flight ticket from Chicago to Orlando International, discover the best prices and exclusive rates for hotels in Orlando International or nearby. You can also compare hundreds of car rental companies at once so you get the best car rental price for your trip.


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Plan the rest of your trip from Chicago to Orlando

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