Cheap Flights from Chicago Midway to Orlando International

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Compare Chicago Midway to Orlando International flight deals

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

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Flight deals from Chicago Midway to Orlando International

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Orlando International Airport? If you want to travel next month, return fares start from $334. Find the lowest prices on one-way and return tickets right here.

Orlando.$196 per passenger.Departing Thu, 26 Nov, returning Thu, 3 Dec.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Chicago Midway on Thu, 26 Nov, arriving in Orlando International.Inbound direct flight with Frontier Airlines departs from Orlando International on Thu, 3 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $196, select.

Orlando.$230 per passenger.Departing Mon, 7 Dec, returning Thu, 10 Dec.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Chicago Midway on Mon, 7 Dec, arriving in Orlando International.Inbound direct flight with Frontier Airlines departs from Orlando International on Thu, 10 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $230, select.

Orlando.$236 per passenger.Departing Mon, 23 Nov, returning Thu, 26 Nov.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Chicago Midway on Mon, 23 Nov, arriving in Orlando International.Inbound direct flight with Frontier Airlines departs from Orlando International on Thu, 26 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $236, select.

Orlando.$334 per passenger.Departing Wed, 21 Oct, returning Sat, 24 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 21 Oct, arriving in Orlando International.Inbound indirect flight with Frontier Airlines, departs from Orlando International on Sat, 24 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $334, select.

Orlando.$379 per passenger.Departing Wed, 28 Oct, returning Wed, 4 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 28 Oct, arriving in Orlando International.Inbound direct flight with Southwest Airlines departs from Orlando International on Wed, 4 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $379, select.

Orlando.$387 per passenger.Departing Wed, 30 Sep, returning Sat, 3 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 30 Sep, arriving in Orlando International.Inbound indirect flight with Frontier Airlines, departs from Orlando International on Sat, 3 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $387, select.

Orlando.$388 per passenger.Departing Sat, 9 Jan, returning Sat, 16 Jan.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 9 Jan, arriving in Orlando International.Inbound indirect flight with Southwest Airlines, departs from Orlando International on Sat, 16 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $388, select.

Orlando.$389 per passenger.Departing Sun, 27 Sep, returning Tue, 29 Sep.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sun, 27 Sep, arriving in Orlando International.Inbound indirect flight with Frontier Airlines, departs from Orlando International on Tue, 29 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $389, select.

Orlando.$462 per passenger.Departing Tue, 13 Oct, returning Fri, 16 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 13 Oct, arriving in Orlando International.Inbound direct flight with Southwest Airlines departs from Orlando International on Fri, 16 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $462, select.

Orlando.$477 per passenger.Departing Mon, 26 Oct, returning Fri, 4 Dec.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 26 Oct, arriving in Orlando International.Inbound indirect flight with Frontier Airlines, departs from Orlando International on Fri, 4 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $477, select.

Orlando.$484 per passenger.Departing Thu, 7 Jan, returning Mon, 11 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 7 Jan, arriving in Orlando International.Inbound direct flight with Southwest Airlines departs from Orlando International on Mon, 11 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $484, select.

Orlando.$515 per passenger.Departing Mon, 26 Oct, returning Fri, 4 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 26 Oct, arriving in Orlando International.Inbound direct flight with Southwest Airlines departs from Orlando International on Fri, 4 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $515, select.

Orlando.$530 per passenger.Departing Sat, 13 Mar, returning Sat, 20 Mar.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Chicago Midway on Sat, 13 Mar, arriving in Orlando International.Inbound direct flight with Frontier Airlines departs from Orlando International on Sat, 20 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $530, select.

Orlando.$554 per passenger.Departing Tue, 29 Sep, returning Tue, 6 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 29 Sep, arriving in Orlando International.Inbound direct flight with Southwest Airlines departs from Orlando International on Tue, 6 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $554, select.

Orlando.$560 per passenger.Departing Wed, 3 Feb, returning Sat, 6 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 3 Feb, arriving in Orlando International.Inbound direct flight with Southwest Airlines departs from Orlando International on Sat, 6 Feb, arriving in Chicago Midway.Price includes taxes and charges.From $560, select.

Orlando.$560 per passenger.Departing Wed, 30 Dec, returning Tue, 5 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 30 Dec, arriving in Orlando International.Inbound direct flight with Southwest Airlines departs from Orlando International on Tue, 5 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $560, select.

Find the cheapest month to fly from Chicago Midway to Orlando International

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

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Direct flights from Chicago Midway to Orlando International

Chicago Midway to Orlando International: Alternative routes

Compare routes from Chicago Midway 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 found	$196
Cheapest month to fly	November
Average flight time	2 hrs, 38 mins
Most popular airline	Southwest Airlines
Average flights per week	49

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

How much are return flights from Chicago Midway to Orlando International?

The best price we found for a return flight from Chicago Midway to Orlando International is $196. 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 International?

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

Which airlines fly direct from Chicago Midway to Orlando International?

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

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

As of September 2026, there are 49 flights per week flying from Chicago Midway to Orlando International.

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

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

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

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Orlando International Airport on Thursday, 26 November 2026.

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

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

How can I find the best flight deal to Orlando International?

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.

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.

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

Currently, Frontier Airlines offers the cheapest flight tickets to Orlando International.

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

Take a direct flight from Chicago Midway Airport to Orlando International Airport and you'll be in the air for an average of 2 hours 35 minutes.
The timezone in Orlando is UTC-5, which is one hour ahead of Chicago.
Flights from MDW to MCO start from 05:00 — the first with Southwest Airlines. The latest departure is at 21:20 with Southwest Airlines. Overall, you can choose from 30 weekly Chicago Midway Airport to Orlando International Airport flights.
For a stress-free journey, arrive at the airport two hours ahead of international flights and one hour before domestic departures. This way, you'll have plenty of time to board your MDW to MCO flight.
During popular months like July, it's a good idea to get to the airport earlier than normal. Arrive two hours before a domestic departure and four hours ahead for international flights whenever you're travelling during a high season in general.
Southwest Airlines has direct flights from Chicago Midway Airport to Orlando International Airport. Book with this popular airline, then get ready to discover the sights in Orlando — and maybe even more of the United States if you have time.
Southwest Airlines is the most frequently booked airline on this route.
Frontier Airlines is a leader in on-time performance for MDW to MCO flights, with 83.72% of services landing on schedule.
If you'd like to add a stop to your trip, simply uncheck 'Direct flights only' when searching for your ticket from Chicago Midway Airport to Orlando International Airport. Here are the most popular stopovers between MDW and MCO:
- Atlanta Hartsfield-Jackson Airport
- Nashville Airport
- Knoxville Airport

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

The cheapest price we've found for a one-way Chicago Midway Airport to Orlando International Airport flight is $177. A round-trip plane ticket is currently $196. Depending on the availability when you book, these fares could change.
It's a good idea to book as early as possible if you're looking for cheap tickets from MDW to MCO. That's because flight prices are based on demand, which tends to increase closer to the date of departure.
May is the cheapest month for flights from Chicago Midway Airport to Orlando International Airport. If you're looking to fly at a different time of year, the 'Whole month' tool will show you the lowest prices for each month.
There's no need to check every day to see if fares have gone down when you create a Price Alert. We'll let you know as soon as there's a change in price on cheap flights from MDW to MCO.
Find the perfect flight for you with the help of the filters. To see the 'Fastest,' 'Best' or 'Cheapest' flights from Chicago Midway Airport to Orlando International Airport, use the 'Sort by' tool. You can also filter by airline, departure and arrival times, and number of stops.

Handy information about Chicago Midway Airport (MDW)

The address for MDW is 5700 South Cicero.
76% of flights leaving from Chicago Midway Airport make it to their destination on time.
To reach Chicago Midway Airport from central Chicago, it'll take about 25 minutes if you're going by car. Of course, this depends on traffic. It's approximately 16 kilometres from the airport to the city centre.
Taking public transport? You can expect a journey time of around 30 minutes.
Catching an early flight from Chicago Midway Airport to Orlando International Airport? Avoid rushing to the terminal (and sneak in some extra precious sleep) by choosing one of these hotels near MDW:

Arriving at Orlando International Airport (MCO)

Consider staying in a hotel near MCO if you're catching a late Chicago Midway Airport to Orlando International Airport flight. Pick one of these options and skip the long transfer:
Grab a Orlando International Airport rental car and discover Orlando and beyond with your own set of wheels. Sonic, Dollar and Budget are well-known companies to choose from here.
Lock in the best deal by booking your vehicle from Orlando International Airport about two weeks ahead of your trip.

When to fly to Orlando International Airport (MCO)

It's time to choose your dates for your flight from Chicago Midway Airport to Orlando International Airport. April is the most popular month to head to Orlando. If you want a more low-key vibe, go in March.
Before locking in your flight from Chicago Midway Airport to Orlando International Airport, think about the kind of weather you like. July is the warmest month in Orlando, with the temperature ranging from 23ºC to 34ºC.
Look for cheap tickets from MDW to MCO in January if you want to travel in cooler conditions. Temperatures are at their lowest around then, ranging between 7ºC and 23ºC on average.

Explore more of the United States

Jacksonville is just one of the many cities in the United States waiting to be explored after you've seen Orlando. Around 209 kilometres away to the north, its top attractions include St. John's Cathedral, Museum of Contemporary Art Jacksonville and The Cummer Museum of Art & Gardens.
Miami is another sought-after destination in the United States and is around 338 kilometres south of Orlando. No journey is complete without visiting Beach, Ocean Drive and Port of Miami.