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Cheap Flights from Chicago Midway (MDW) to Orlando International (MCO)

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 to Orlando International? Find the lowest prices on one-way and return tickets right here.
Orlando.£43 per passenger.Departing Mon, 12 Jan, returning Thu, 15 Jan.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Chicago Midway on Mon, 12 Jan, arriving in Orlando International.Inbound direct flight with Frontier Airlines departs from Orlando International on Thu, 15 Jan, arriving in Chicago Midway.Price includes taxes and charges.From £43, select.
Orlando.£49 per passenger.Departing Sun, 1 Feb, returning Thu, 5 Feb.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Chicago Midway on Sun, 1 Feb, arriving in Orlando International.Inbound direct flight with Frontier Airlines departs from Orlando International on Thu, 5 Feb, arriving in Chicago Midway.Price includes taxes and charges.From £49, select.
Orlando.£62 per passenger.Departing Sun, 1 Mar, returning Tue, 3 Mar.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sun, 1 Mar, arriving in Orlando International.Inbound indirect flight with Frontier Airlines, departs from Orlando International on Tue, 3 Mar, arriving in Chicago Midway.Price includes taxes and charges.From £62, select.
Orlando.£62 per passenger.Departing Sat, 31 Jan, returning Thu, 5 Feb.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 31 Jan, arriving in Orlando International.Inbound indirect flight with Frontier Airlines, departs from Orlando International on Thu, 5 Feb, arriving in Chicago Midway.Price includes taxes and charges.From £62, select.
Orlando.£63 per passenger.Departing Mon, 26 Jan, returning Thu, 5 Mar.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Chicago Midway on Mon, 26 Jan, arriving in Orlando International.Inbound direct flight with Frontier Airlines departs from Orlando International on Thu, 5 Mar, arriving in Chicago Midway.Price includes taxes and charges.From £63, select.
Orlando.£64 per passenger.Departing Sun, 8 Feb, returning Thu, 5 Mar.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Chicago Midway on Sun, 8 Feb, arriving in Orlando International.Inbound direct flight with Frontier Airlines departs from Orlando International on Thu, 5 Mar, arriving in Chicago Midway.Price includes taxes and charges.From £64, select.
Orlando.£65 per passenger.Departing Mon, 26 Jan, returning Mon, 2 Feb.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Chicago Midway on Mon, 26 Jan, arriving in Orlando International.Inbound direct flight with Frontier Airlines departs from Orlando International on Mon, 2 Feb, arriving in Chicago Midway.Price includes taxes and charges.From £65, select.
Orlando.£70 per passenger.Departing Sun, 1 Mar, returning Thu, 5 Mar.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Chicago Midway on Sun, 1 Mar, arriving in Orlando International.Inbound direct flight with Frontier Airlines departs from Orlando International on Thu, 5 Mar, arriving in Chicago Midway.Price includes taxes and charges.From £70, 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 January.
Dec
from £128
Jan
from £43
Feb
from £49
Mar
from £62
Apr
from £127
May
from £310
Jun
from £315
Jul
from £326
Aug
from £310
Sep
from £311
Oct
from £334
Nov
Find prices

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£43
Cheapest month to flyJanuary
Average flight time2 hrs, 40 mins
Most popular airlineSouthwest Airlines
Average flights per week71

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

The best price we found for a return flight from Chicago Midway to Orlando International is £43. 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 International.
Southwest Airlines, Frontier Airlines and Volaris fly direct from Chicago Midway to Orlando International.
As of December 2025, there are 71 flights per week flying from Chicago Midway to Orlando International.
The cheapest month to fly from Chicago Midway to Orlando International is usually January.
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 Monday, 12 January 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 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.
Currently, Frontier Airlines offers the cheapest flight tickets to Orlando International.

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

  • The average time for a direct flight from Chicago Midway International Airport to Orlando International Airport is 2 hours 40 minutes.

  • The timezone in Orlando is UTC-4, which is one hour ahead of Chicago.

  • Every week, there are 41 Chicago Midway International Airport to Orlando International Airport flights. If you want to jet off as early as possible, opt for the 05:00 Southwest Airlines flight. If you'd rather make the most of your time before flying, the last departure is at 21:50 with Southwest Airlines.

  • Give yourself plenty of time to catch your MDW to MCO flight. It's generally best to arrive at least two hours before international departures and an hour ahead for domestic flights.

  • During popular months such as July, it's best to get to the airport earlier than normal. Plan to arrive two hours before a domestic departure and four hours ahead for international flights when you travel during a peak period in general.

  • Frontier Airlines is your ticket to exploring Orlando (and maybe even some other great parts of United States!). Check out the direct flights from Chicago Midway International Airport to Orlando International Airport offered by this popular airline.

  • Frontier Airlines tops the list for bookings on this route.

  • With a dependable 83.02% of services arriving as scheduled, Frontier Airlines is the most punctual carrier for MDW to MCO flights.

  • If you'd like to explore another city along the way, simply deselect 'Direct flights only' when searching for your ticket from Chicago Midway International Airport to Orlando International Airport. Here are the top stopovers between MDW and MCO:

    • Hartsfield-Jackson Atlanta International Airport

    • McGhee Tyson Airport

    • Nashville International Airport

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

  • The lowest price we've found for a one-way Chicago Midway International Airport to Orlando International Airport flight is £22. A return ticket is currently £43. Depending on the availability and when you book, these fares may change.

  • To get cheap tickets from MDW to MCO, book your trip six months before your departure date.

  • The cheapest month for flights from Chicago Midway International Airport to Orlando International Airport is May. Use the 'Whole month' tool to see the lowest airfares if you have a flexible travel schedule.

  • Never miss a deal on cheap flights from MDW to MCO by setting up a Price Alert. We'll send you an email or notification through the app when fares go down.

  • Lock in the right flight for you with the help of the filters. To see the 'Best,' 'Fastest' or 'Cheapest' flights from Chicago Midway International Airport to Orlando International Airport, use the 'Sort by' function. You can also filter by arrival and departure times, airline, and number of stops.

Handy information about Chicago Midway International Airport (MDW)

  • MDW is located at 5700 South Cicero.

  • When it comes to Chicago Midway International Airport's on-time performance, data shows 77.88% of flights arrive within the scheduled timeframe.

  • Central Chicago to Chicago Midway International Airport is around 12 miles. Depending on traffic, it'll take you about 20 minutes to get there if you're driving, ride-sharing or catching a cab.

  • The trip on public transport takes roughly 45 minutes.

  • Searching for a handy hotel close to MDW? If you've booked an early flight from Chicago Midway International Airport to Orlando International Airport, these accommodation options will put you moments from your check-in counter:

Arriving at Orlando International Airport (MCO)

Getting from Orlando International Airport (MCO) to central Orlando

  • You'll find MCO at One Airport Boulevard.

  • Orlando International Airport to the centre of Orlando has a drive time of around 20 minutes. It's approximately 20 miles away.

When to fly to Orlando International Airport (MCO)

  • July is the most popular month for flights from Chicago Midway International Airport to Orlando International Airport. To escape the crowds, visit Orlando in May.

  • The warmest month in Orlando is July, with the temperature ranging between 23ºC (73ºF) and 34ºC (93ºF). Lock in your flights from Chicago Midway International Airport to Orlando International Airport in this month if this is the type of weather you like.

  • Look for cheap tickets from MDW to MCO in January if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between 7ºC (45ºF) and 23ºC (73ºF) on average.

Explore more of United States

  • Jacksonville is just one of the many places in United States waiting to be discovered once you've seen the sights of Orlando. Around 130 miles away to the north, its best attractions include Jacksonville Zoo and Gardens, The Cummer Museum of Art & Gardens and Friendship Fountain.

  • Miami is another well-known destination in United States and is around 210 miles south of Orlando. No trip is complete without seeing 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.