How long is the flight from Chicago Midway Airport to Orlando?

There are many flights that can get you from Chicago Midway Airport to Orlando in 2h 30m. Fly via Southwest, Frontier, or Allegiant Air to get the fastest option. The distance between Chicago Midway Airport and Orlando is about 990 mi. Both multi-stop and nonstop flights can be found to your destination and back.

What are the cheapest airlines flying from Chicago Midway Airport to Orlando round-trip?

Currently priced at $63, Spirit Airlines will fly you from Chicago Midway Airport to Orlando and back. In addition to Spirit Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Frontier and Delta - these airlines can fly you to your destination from $100 and $196, respectively. Spirit Airlines is priced at 76% lower than the current average price of a flight leaving 3 months from now.

What are the cheapest airlines to fly from Chicago Midway Airport to Orlando one-way?

The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $54. However, be on the lookout for offers from Southwest and Allegiant Air, as they are both options that can get you from Chicago Midway Airport to Orlando for a low price.

How far ahead should I book a flight from Chicago Midway Airport to Orlando?

To ensure you get the cheapest price possible for a flight from Chicago Midway Airport to Orlando, you should look to book at least 31 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago Midway Airport to Orlando?

Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Orlando (average of $206). Flying from Chicago Midway Airport to Orlando in November is currently the most expensive (average of $289). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest day to fly from Chicago Midway Airport to Orlando?

Travelers seeking maximum savings on their Chicago Midway Airport to Orlando flight should consider departing on Monday evenings when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

In terms of precipitation, rainfall in Orlando ranges from 2.4 - 8.7 inches per month. June is typically the wettest month, when rainfall can reach 8.7 in. November is typically the driest time to visit Orlando when rainfall is around 2.4 in.

If weather is an important factor for your trip to Orlando, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 60.8 F).

What are the cheapest flights from Chicago Midway Airport to Orlando?

Looking at all options, your cheapest flight can be booked for $43. While the most popular route (Chicago Midway - Orlando) can be booked for $103 on average, our data indicates $193 when flying from Chicago Midway Airport to Orlando.

What are the most popular airlines that fly from Chicago Midway Airport to Orlando?

Delta, Frontier and Spirit Airlines are the most popular airlines when flying from Chicago Midway Airport to Orlando.

What is the cheapest day to fly round-trip from Chicago Midway Airport to Orlando?

Flights from Chicago Midway Airport to Orlando are found to be more expensive on Tuesday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Orlando.

How far in advance should I book a flight from Chicago Midway Airport to Orlando?

To save up to 44% on this flight, we recommend booking at least 30 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago Midway Airport to Orlando from $166 1-2 weeks out and tickets from $338 for flights departing within the next 72 hours.

What is the cheapest month to fly from Chicago Midway Airport to Orlando?

August is one of the best times of the year to fly to Orlando from Chicago Midway Airport. Prices for August average $244 per person but you can even find prices for as low as $88. The most expensive prices can be found in the month of March. Opting for a August flight can save you 38% on your journey compared to booking in March

What is the cheapest time of day to fly from MDW to ORL?

It’s typically best to fly out from Chicago Midway Airport to Orlando in the evening. Doing so could potentially save you 11% on the flight price compared to flying in the morning, which is usually more expensive.

Can I find deals for flights from Midway to Orlando that include hotel bookings?

Yes. In addition to deals on Midway to Orlando flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Midway to Orlando?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Orlando.

Can I find deals for business class flights from Midway to Orlando?

Yes. Cheapflights offers flight deals from Midway to Orlando by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$50+ Flights from Chicago Midway Airport to Orlando

Round-trip from	$103 (Cheapflightsfares)
One-way from	$50 (Cheapflightsfares)
Popular in	December
Cheapest in	September
Average price	$197
Good round-trip deal	$141 or less
Good one-way deal	$78 or less

Southwest offers free snacks and non-alcoholic beverages, enhancing your in-flight experience.

Southwest's Rapid Rewards program offers points for every dollar spent, with no blackout dates.

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$63	Average$193	FlexibilityNo cancel fee	On-time65%
Frontier	Cheapest$100	Average$213	FlexibilityNo cancel fee	On-time62%
Delta	Cheapest$196	Average$403	FlexibilityNo cancel fee	On-timeN/A
Southwest	Cheapest$214	Average$394	FlexibilityNo cancel fee	On-time63%
United Airlines	Cheapest$259	Average$364	FlexibilityNo cancel fee	On-time69%

$50+ Cheap flights from Midway (MDW) to Orlando (ORL)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/29. Fares are subject to change and may not be available on all flights or dates of travel.

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Cheapflights Tip: The best prices from Chicago Midway to Orlando are usually found in September or July, booked 31 days in advance, depart on a Thursday or Friday and return on a Friday

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Cheapest flights from Midway to OrlandoExplore the most affordable flight options available from Midway to Orlando. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

Explore the most affordable flight options available from Midway to Orlando. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

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The best insider tips for Chicago Midway Airport to Orlando flights

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Best time to book a flight from Midway to Orlando

Have a flexible travel schedule? Discover the best time to fly to Orlando from Midway with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Orlando

How far ahead should I book a flight from Chicago Midway Airport to Orlando?

Use this chart to determine the optimal time to book a round-trip flight from Midway to Orlando. Price data was last updated on August 29, 2025.

What is the cheapest month to book a flight from Chicago Midway Airport to Orlando?

What is the cheapest time of day to fly from MDW to ORL?

Find hourly flight availability from Midway to Orlando. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

What is the cheapest day to fly from Chicago Midway Airport to Orlando?

Use this chart to determine the cheapest time to fly round-trip from Midway to Orlando. Price data was last updated on September 7, 2025.

Reviews of airlines servicing Orlando

Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Chicago Midway Airport to Orlando. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Midway to Orlando. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

How long is the flight from Chicago Midway Airport to Orlando?

What are the cheapest airlines flying from Chicago Midway Airport to Orlando round-trip?

What are the cheapest airlines to fly from Chicago Midway Airport to Orlando one-way?

What are the cheapest flights from Chicago Midway Airport to Orlando?

Can I find deals for flights from Midway to Orlando that include hotel bookings?

How can I find direct flights from Midway to Orlando?

Can I find deals for business class flights from Midway to Orlando?

What is the cheapest month to book a flight from Chicago Midway Airport to Orlando?

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Alternative routes for Midway to Orlando

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Top 5 airlines flying from Midway to Orlando

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Cheapest flights from Midway to Orlando
Explore the most affordable flight options available from Midway to Orlando. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.