Cheap Flights from Chicago Midway to Orlando

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Compare Chicago Midway to Orlando flight deals

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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 Airport to Orlando? If you want to travel next month, return fares start from $285. Find the lowest prices on one-way and return tickets right here.

Orlando.$285 per passenger.Departing Fri, 14 Aug, returning Wed, 19 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Fri, 14 Aug, arriving in Orlando International.Inbound indirect flight with Frontier Airlines, departs from Orlando International on Wed, 19 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $285, select.

Orlando.$289 per passenger.Departing Fri, 28 Aug, returning Wed, 2 Sep.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Fri, 28 Aug, arriving in Orlando International.Inbound indirect flight with Frontier Airlines, departs from Orlando International on Wed, 2 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $289, select.

Orlando.$292 per passenger.Departing Sat, 5 Sep, returning Wed, 9 Sep.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 5 Sep, arriving in Orlando International.Inbound indirect flight with Frontier Airlines, departs from Orlando International on Wed, 9 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $292, select.

Orlando.$327 per passenger.Departing Sat, 3 Oct, returning Mon, 5 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 3 Oct, arriving in Orlando International.Inbound direct flight with Southwest Airlines departs from Orlando International on Mon, 5 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $327, select.

Orlando.$327 per passenger.Departing Tue, 3 Nov, returning Thu, 5 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 3 Nov, arriving in Orlando International.Inbound direct flight with Southwest Airlines departs from Orlando International on Thu, 5 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $327, select.

Orlando.$327 per passenger.Departing Mon, 28 Sep, returning Thu, 1 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 28 Sep, arriving in Orlando International.Inbound direct flight with Southwest Airlines departs from Orlando International on Thu, 1 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $327, select.

Orlando.$327 per passenger.Departing Mon, 10 Aug, returning Wed, 12 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 10 Aug, arriving in Orlando International.Inbound direct flight with Southwest Airlines departs from Orlando International on Wed, 12 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $327, select.

Orlando.$327 per passenger.Departing Sat, 12 Sep, returning Mon, 14 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 12 Sep, arriving in Orlando International.Inbound direct flight with Southwest Airlines departs from Orlando International on Mon, 14 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $327, select.

Orlando.$328 per passenger.Departing Tue, 25 Aug, returning Tue, 1 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 25 Aug, arriving in Orlando International.Inbound direct flight with Southwest Airlines departs from Orlando International on Tue, 1 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $328, select.

Orlando.$338 per passenger.Departing Sat, 31 Oct, returning Sat, 7 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 31 Oct, arriving in Orlando International.Inbound indirect flight with Southwest Airlines, departs from Orlando International on Sat, 7 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $338, select.

Orlando.$339 per passenger.Departing Sat, 5 Dec, returning Tue, 8 Dec.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 5 Dec, arriving in Orlando International.Inbound indirect flight with Southwest Airlines, departs from Orlando International on Tue, 8 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $339, select.

Orlando.$351 per passenger.Departing Wed, 9 Dec, returning Mon, 14 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 9 Dec, arriving in Orlando International.Inbound direct flight with Southwest Airlines departs from Orlando International on Mon, 14 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $351, select.

Orlando.$351 per passenger.Departing Sat, 31 Oct, returning Mon, 2 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 31 Oct, arriving in Orlando International.Inbound direct flight with Southwest Airlines departs from Orlando International on Mon, 2 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $351, select.

Orlando.$381 per passenger.Departing Tue, 28 Jul, returning Tue, 11 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 28 Jul, arriving in Orlando International.Inbound indirect flight with Frontier Airlines, departs from Orlando International on Tue, 11 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $381, select.

Orlando.$393 per passenger.Departing Wed, 29 Jul, returning Wed, 29 Jul.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 29 Jul, arriving in Orlando International.Inbound indirect flight with Southwest Airlines, departs from Orlando International on Wed, 29 Jul, arriving in Chicago Midway.Price includes taxes and charges.From $393, select.

Orlando.$421 per passenger.Departing Tue, 15 Dec, returning Wed, 6 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 15 Dec, arriving in Orlando International.Inbound direct flight with Southwest Airlines departs from Orlando International on Wed, 6 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $421, select.

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 August.

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Direct flights from Chicago Midway to Orlando

Alternative Chicago Midway to Orlando routes

Looking for the cheapest, fastest or easiest route from Chicago Midway to Orlando? You could fly into the following airports instead.

Chicago to Orlando: Flight information

The things to know before you go.

Cheapest flight found	$285
Cheapest month to fly	August
Average flight time	2 hrs, 38 mins
Most popular airline	Southwest Airlines
Average flights per week	56

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

How many airports are there in Orlando?

There are 5 airports in Orlando: Orlando International, Orlando Sanford, Daytona Beach, Lakeland, and Melbourne Orlando International.

How much are return flights from Chicago Midway to Orlando?

The best price we found for a return flight from Chicago Midway to Orlando is $285. 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.

How long does it take to fly from Chicago Midway to Orlando?

2 hours and 38 minutes is the average flight time from Chicago Midway to Orlando.

Which airlines fly direct from Chicago Midway to Orlando?

Southwest Airlines, Frontier Airlines and Volaris fly direct from Chicago Midway to Orlando.

How many flights are there a week from Chicago Midway to Orlando?

As of July 2026, there are 56 flights per week flying from Chicago Midway to Orlando.

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

The cheapest month to fly from Chicago Midway to Orlando is usually August.

Which is the cheapest airport to fly into in Orlando?

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 $285.

Which upcoming date is cheapest to fly from Chicago Midway Airport to Orlando on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Orlando on Friday, 14 August 2026.

Can I get a direct flight from Chicago Midway Airport to Orlando?

Yes – the average flight time is 2 hours and 38 minutes.

How can I get the best flight deal from Chicago Midway Airport to Orlando?

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.

When is the best time to book flights to Orlando?

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.

What’s the weather like in Orlando?

In July, the average temperature is usually around 27°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.

Which is the cheapest airline to fly from Chicago Midway Airport to Orlando with?

Currently, Frontier Airlines and Southwest Airlines offer the cheapest flight tickets to Orlando.

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

Expect to be travelling for 2 hours 50 minutes. That's the average journey time for a direct flight from Chicago Midway International Airport to Orlando.
Chicago Midway International Airport is located in Chicago. Based in the UTC-5 timezone, Orlando is one hour ahead of Chicago.
Chicago Midway International Airport (MDW) to Orlando International Airport (MCO) is the most traveled route, with 37 weekly departures to pick from. If you have things to do before heading off, the last flight from MDW to MCO is with Southwest Airlines at 21:20. Choose the first departure with Southwest Airlines at 05:00 if you want to fly out earlier.
Leave plenty of time to get on your MDW to Orlando flight. As a general rule, turn up at least two hours before international departures and an hour ahead for domestic flights.
Be prepared for longer queues in popular months like July. Arriving up to four hours in advance for international flights and two hours for domestic departures will help ensure a smooth travel experience.
Direct Chicago Midway International Airport to Orlando tickets are available for booking. Orlando International Airport (MCO) is where you'll be touching down.
Keep an eye out for offers from Southwest Airlines. This airline has direct flights from Chicago Midway International Airport to Orlando.
Located around 14 kilometres from central Chicago, MDW can be reached in about 25 minutes by car, depending on traffic. The journey on public transport will take roughly 30 minutes.
Catching an early flight from Chicago Midway International Airport to Orlando? Avoid rushing to the terminal (and sneak in some extra snooze time) by choosing one of these hotels near MDW:
When it comes to Chicago Midway International Airport's on-time performance, 76% of flights arrive within the expected time frame.
MDW's address is 5700 South Cicero.

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

$142 is currently the best price for a one-way Chicago Midway International Airport to Orlando flight. A return plane ticket starts at $285. These fares can change depending on availability and demand.
Booking ahead of time is often the key to scoring a cheap flight from MDW to Orlando. Fares tend to rise as demand increases, so the closer you get to departure, the more expensive your ticket may be.
The 'Whole month' tool will show you the cheapest tickets from Chicago Midway International Airport to Orlando throughout the month. It's an easy way to snap up a bargain if your plans are flexible.
Save time searching for cheap flights from MDW to Orlando by setting up a Price Alert. You'll get an email or notification on the app when a new discounted fare appears.
Select your preferred departure and arrival times, number of stops and airlines with our filters. Then, sort the results for your flight from Chicago Midway International Airport to Orlando by 'Cheapest,' 'Best' or 'Fastest.'

Airports in Orlando

Orlando International Airport (MCO)

The distance from Orlando International Airport (MCO) to central Orlando is roughly 19 kilometres. It takes around 25 minutes to get to the centre driving.
If you're taking public transport, expect a journey time of around 1 hour.
If you're coming in on a late flight from Chicago Midway International Airport to Orlando, few things beat the convenience of staying close to the terminal. Grab your luggage from the carousel and then be showered and relaxing soon after at one of these accommodation options near MCO:
Lock in the best deal by reserving your ride from Orlando International Airport about two weeks ahead of your flight from MDW to Orlando.
MCO is located at One Airport Boulevard.

Orlando Sanford International Airport (SFB)

Central Orlando is around 40 kilometres from Orlando Sanford International Airport (SFB). After your flight from Chicago Midway International Airport to Orlando has hit the runway and you've made your way to arrivals, expect a drive of around 35 minutes.
You can expect the trip to take roughly 1 hour on public transport.
There are some comfortable places to drop your things at near SFB. Kick back and get cosy after your MDW to Orlando flight at any of these perfectly located options:
Lock in the lowest price by booking your ride from SFB one week ahead of time. You'll also have access to a bigger selection of vehicles.

Best time to go to Orlando

March is the most popular month for flights from Chicago Midway International Airport to Orlando. To steer clear of the crowds, visit Orlando in December.
Lock in a Chicago Midway International Airport to Orlando plane ticket with a departure in July if you want to experience the city during its warmest month. Expect temperatures to range from 23ºC to 34ºC.
Search for cheap tickets from MDW to Orlando in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between 7ºC and 23ºC on average.

More about Orlando

After booking your flight from Chicago Midway International Airport to Orlando, find a hotel that offers both comfort and a great location. Make one of these options your base for exploring Orlando:
There are so many things to discover in this city it can be tricky to know where to start. Universal's Islands of Adventure, Hogwarts and Jurassic world are top attractions which should feature on every Orlando itinerary.

Explore more of the United States

You've seen Orlando, now it's time to discover more of the United States. Journey around 209 kilometres north to Jacksonville to check off its must-visit sights. From St. John's Cathedral to Museum of Contemporary Art Jacksonville and The Cummer Museum of Art & Gardens, you'll have a full itinerary ahead.
Miami is another essential stop in the United States and is around 338 kilometres south of Orlando. No journey is complete without seeing Beach, Ocean Drive and Port of Miami.