Flight tickets from Orlando to Chicago Midway

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Flight deals from Orlando to Chicago Midway Airport

Looking for a cheap last-minute deal or the best return flight from Orlando to Chicago Midway Airport? If you want to travel next month, return fares start from ₹ 8,304. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Orlando to Chicago Midway

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

Direct flights from Orlando to Chicago Midway

Orlando to Chicago: Flight information

The things to know before you go.
Cheapest flight found₹ 2,106
Cheapest month to flyMay
Average flight time2 hrs, 56 mins
Most popular airlineSouthwest Airlines
Average flights per week47

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

The best price we found for a return flight from Orlando to Chicago Midway is ₹ 8,304. 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 56 minutes is the average flight time from Orlando to Chicago Midway.
Southwest Airlines, Volaris and Frontier Airlines fly direct from Orlando to Chicago Midway.
As of February 2026, there are 47 flights per week flying from Orlando to Chicago Midway.
The cheapest month to fly from Orlando to Chicago Midway is usually March.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Orlando to Chicago Midway Airport on Wednesday, 11 March 2026.
Yes – the average flight time is 2 hours and 56 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 Chicago Midway 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 Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Chicago Midway is Frontier Airlines .

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

  • Your next great adventure starts at one of Orlando's main airports, Orlando International Airport (MCO) or Orlando Sanford International Airport (SFB). Explore your options for booking a flight from Orlando to Chicago Midway International Airport (MDW) leaving from either of these.

  • The average length of a direct Orlando to Chicago Midway International Airport flight is 2 hours 50 minutes.

  • Chicago is one hour behind Orlando. Chicago Midway International Airport is located in Chicago, which operates on the UTC-5 timezone.

  • Orlando International Airport (MCO) to Chicago Midway International Airport (MDW) is the most popular route. There are 31 direct weekly departures to choose from. If you prefer starting your day later, take the last flight with Southwest Airlines at 10:50pm. Choose the first MCO to MDW departure with Frontier Airlines at 6am if you'd rather get going earlier.

  • Your flight from Orlando to MDW won't wait if you're late, so get to the airport with time to spare. Arrive up to one hour in advance for domestic flights and two hours ahead for international travel.

  • Peak season means busier airports, so aim to get there even earlier. Give yourself at least two hours before a domestic flight and four hours for an international journey to keep to your schedule.

Airports in Orlando

Orlando International Airport (MCO)

  • You can take a direct flight from Orlando to Chicago Midway International Airport (MDW) leaving from Orlando International Airport (MCO).

  • Southwest Airlines is a popular carrier that operates direct flights from Orlando to Chicago Midway International Airport leaving from MCO.

  • The majority of passengers choose to fly with Southwest Airlines between MCO and MDW.

  • The carrier with the best on-time arrival rate on this route is Frontier Airlines.

  • The distance from central Orlando to MCO is around 32 kilometres. Depending on traffic, it'll take you about 20 minutes to get there if you're catching a cab, ride-sharing or driving.

  • Planning to catch an early flight from Orlando to Chicago Midway International Airport? Avoid the last-minute rush to the terminal (and enjoy a little extra shut-eye) by choosing one of these hotels near Orlando International Airport:

  • When it comes to Orlando International Airport's on-time performance, data shows 78.28% of flights stick to their scheduled arrival time.

  • The address for MCO is One Airport Boulevard.

Orlando Sanford International Airport (SFB)

  • Using public transport, you can travel from central Orlando to SFB in around 2 hours 5 minutes. The terminal is roughly 48 kilometres away, and getting there by car will take approximately 35 minutes.

  • Want to treat yourself to an extra night away before catching your Orlando to MDW flight? Check in to a hotel near Orlando Sanford International Airport before your break officially starts. These stays have a room with your name on it:

  • When it comes to keeping flights punctual, Orlando Sanford International Airport has an on-time arrival rate of 69.11%.

About Chicago Midway International Airport (MDW)

  • The last thing you want is a long journey to your hotel if you're arriving on a late flight from Orlando to Chicago Midway International Airport. Get comfy at one of these accommodation options near MDW instead:

  • Grab a Chicago Midway International Airport rental car and explore Chicago and beyond with your own set of wheels. Dollar, Hertz and Budget are popular outlets you can book with here.

  • Lock in the best possible rate by reserving your vehicle around four weeks ahead of your Orlando to Chicago Midway International Airport flight.

  • MDW is located at 5700 South Cicero.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • Central Chicago is around 14 kilometres from Chicago Midway International Airport. Journey times by cab or car hire will vary depending on time of day and traffic conditions, so do a little research ahead of time.

  • It typically takes 45 minutes if you're travelling by public transport.

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

  • ₹ 2,106 is currently the lowest price for a one-way ticket from Orlando to Chicago Midway International Airport. A return flight starts from ₹ 8,304. These fares may change depending on demand.

  • Booking ahead of time is often the key to scoring a cheap flight from Orlando to MDW. Airlines adjust prices based on demand, so the closer your departure date, the more it could cost you.

  • Affordable Orlando to Chicago Midway International Airport tickets are easier to find if your travel dates are flexible. Try using the 'Whole month' search function to compare fares across every month and then choose the cheapest day.

  • Be the first to know about deals for flight tickets from Orlando to MDW by setting up a Price Alert. We'll send you an email or notification on the app when a lower fare pops up.

  • Save money on your flight from Orlando to Chicago Midway International Airport by using the search filters. Select your ideal times, airlines and number of stops, then sort the results by 'Cheapest' for the best deals.

The best time to fly from Orlando to Chicago Midway International Airport (MDW)

  • It's time to work out your travel dates for your flight from Orlando to Chicago Midway International Airport (MDW). July is the busiest month to travel to Chicago. If you like your getaways a little more chill, go in May.

  • When booking your Orlando to MDW flight ticket, consider the kind of weather forecast you're hoping for. July is the warmest month in Chicago, with temperatures ranging from 15ºC to 29ºC.

  • If you want cooler conditions, look for a cheap ticket from Orlando to Chicago Midway International Airport in January when temperatures are between -12ºC and 3ºC.

More about Chicago

Explore more of the United States

  • Chicago has plenty to offer, but there are so many other corners of the United States you should also see. About 257 kilometres south-east of Chicago, a trip to Indianapolis will keep your itinerary busy. Start with leading attractions like 9-11 Memorial, Lucas Oil Stadium and Eiteljorg Museum.

  • Milwaukee is another essential stop in the United States and is around 137 kilometres north of Chicago. No trip is complete without dropping by Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo.

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