Cheap Flights from Chicago Midway to Orlando

Compare Chicago Midway to Orlando flight deals

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

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Flight deals from Chicago Midway to Orlando

Looking for a cheap last-minute deal or the best return flight from Chicago Midway to Orlando? Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago Midway to Orlando

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Orlando flights are currently cheapest in March.

Direct flights from Chicago Midway to Orlando

Chicago to Orlando: Flight information

The things to know before you go.
Cheapest flight foundRs12,017
Cheapest month to flyMarch
Average flight time2 hrs, 40 mins
Most popular airlineSouthwest Airlines
Average flights per week50

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

There are 5 airports in Orlando: Orlando International, Orlando Sanford, Daytona Beach, Lakeland, and Melbourne Orlando International.
The best price we found for a return flight from Chicago Midway to Orlando is Rs18,727. 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 40 minutes is the average flight time from Chicago Midway to Orlando.
Southwest Airlines, Frontier Airlines and Volaris fly direct from Chicago Midway to Orlando.
As of February 2026, there are 50 flights per week flying from Chicago Midway to Orlando.
The cheapest month to fly from Chicago Midway to Orlando is usually April.
If you're flying from Chicago Midway Airport, the cheapest airport near Orlando is Orlando International – which is 12.9 km away from the centre of Orlando. We've found flights into this airport from Rs18,727.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Orlando on Saturday, 25 April 2026.
Yes – the average flight time is 2 hours and 40 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 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.
In February, the average temperature is usually around 17°C. August is typically the warmest month in Orlando, when it usually averages around 31°C. You can expect the least rain in November. The coldest month is January, with temperatures averaging 9°C. The rainiest month is June.
Currently, Frontier Airlines offers the cheapest flight tickets to Orlando.

Flying from Chicago Midway International Airport (MDW) to Orlando: what you need to know

  • Around 2 hours 50 minutes is how long you'll be travelling on a direct flight from Chicago Midway International Airport to Orlando.

  • Chicago Midway International Airport is located in Chicago. Following the UTC-4 timezone, Orlando is one hour ahead of Chicago.

  • With 30 weekly flights between the two airports, Chicago Midway International Airport (MDW) to Orlando International Airport (MCO) is the most popular route. Southwest Airlines operates the earliest flight at 05:00. If you're eager to get more out of your day before leaving, the latest departure from MDW to MCO is with Southwest Airlines at 21:20.

  • For a smooth journey, arrive at the airport two hours ahead of international flights and one hour before domestic departures. This will give you plenty of time to catch your MDW to Orlando flight.

  • Taking off during a peak period like public or school holidays? Expect longer lines at security and check-in. Give yourself extra leeway and arrive up to four hours before international flights and two hours before domestic departures.

  • Direct Chicago Midway International Airport to Orlando tickets are available for booking. Orlando International Airport (MCO) is where you'll disembark.

  • Look out for promotions from Southwest Airlines. This airline has direct flights from Chicago Midway International Airport to Orlando.

  • Located around 14 kilometres from the centre of Chicago, MDW can be reached in about 20 minutes by car (depending on traffic). The journey on public transport takes roughly 45 minutes.

  • Planning to catch an early flight from Chicago Midway International Airport to Orlando? Avoid the stress of rushing to the terminal (and sneak in some extra snooze time) by choosing one of these hotels close to MDW:

  • Of all flights departing from Chicago Midway International Airport, 77.88% touch down on time at their destination.

  • The address for MDW is 5700 South Cicero.

How to find the cheapest flights from Chicago Midway International Airport (MDW) to Orlando

  • Rs12,017 is currently the best price for a one-way Chicago Midway International Airport to Orlando flight. A return flight ticket starts from Rs18,727. These fares can change depending on availability.

  • Get cheap flights from MDW to Orlando by booking one month ahead. According to our research, that's the best time for finding the biggest deals.

  • The best month for scoring cheap Chicago Midway International Airport to Orlando tickets is May. Use the 'Whole month' tool to compare all available prices, then select the dates with the lowest fares.

  • You don't need to check back in every day to find out if fares have dropped when you set up a Price Alert. We'll notify you as soon as there's an even bigger deal on cheap flights from MDW to Orlando.

  • Pick your preferred arrival and departure times, number of stops and airlines with our filters. Then, sort the results for your flight from Chicago Midway International Airport to Orlando by 'Best,' 'Fastest' or 'Cheapest.'

Airports in Orlando

Orlando International Airport (MCO)

Orlando Sanford International Airport (SFB)

  • Orlando Sanford International Airport (SFB) is around 48 kilometres from central Orlando. After your flight from Chicago Midway International Airport to Orlando, it'll take you around 35 minutes to get to the heart of the city in a ride-share or cab.

  • Public transport will get you there in around 2 hours 5 minutes.

  • Place the 'Do not disturb' sign on your door and relax at a hotel close to SFB. Here are a few options where you can take a load off after your MDW to Orlando flight:

  • Dollar, Hertz and Budget make picking up an Orlando Sanford International Airport rental car simple. These trusted providers are located in or around the terminal and will have you ready to go in a flash.

  • Score the best price by reserving your ride from SFB one week in advance. You can also expect to have a greater selection of vehicles.

Best time to go to Orlando

  • Before securing your flights from Chicago Midway International Airport to Orlando, consider which time of year works best for you. High season in Orlando offers a lively atmosphere and plenty to do, while the off-season means you'll get cheaper deals on hotels and smaller crowds.

  • Before booking a Chicago Midway International Airport to Orlando flight ticket, think about the kind of weather you prefer. July is the warmest month in Orlando, with temperatures ranging from 23ºC to 34ºC.

  • If you like cooler conditions, look for a cheap ticket from MDW to Orlando in January when temperatures average between 7ºC and 23ºC.

More about Orlando

Explore more of United States

  • Orlando has loads to offer, but there are so many other corners of United States you'll want to see. About 209 kilometres north of Orlando, a trip to Jacksonville will keep you on the move. Start with popular sights like Jacksonville Zoo and Gardens, The Cummer Museum of Art & Gardens and Friendship Fountain.

  • Miami is another standout destination in United States and is around 338 kilometres south of Orlando. No journey is complete without a visit to Wynwood Walls, Vizcaya Museum and Gardens and American Airlines Arena.

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