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$64+ 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ORL
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
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The best prices from Chicago Midway to Orlando are usually found in May or April, booked 88 days in advance, depart on a Thursday or Sunday and return on a Friday

Cheap flight deals from Midway to Orlando

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Orlando (ORL). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 18, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$128
(Frontier)

One-way from

$64
(Cheapflightsfares)

Popular in

June

Cheapest in

May

Average price

$304
Provider with most accurate pricing for Chicago Midway-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Orlando (ORL) flights.
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From Chicago Midway to Orlando (ORL)
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One-way flight from Chicago Midway to Orlando (ORL)
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High demand for flights, 25% potential price rise
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Best time to find cheap flights, 18% potential price drop
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Average for round-trip flights in December 2024
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Find flight deals from Midway to Orlando

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 December 18, 2024.

This Mytrip deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/312:20 pmMDW - MCO
1 stop8h 23mFrontier
Wed 1/87:30 pmMCO - MDW
1 stop17h 18mFrontier
Deal found 12/16$129
This Southwest deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/245:00 pmMDW - MCO
1 stop4h 25mSouthwest
Tue 12/313:50 pmMCO - MDW
1 stop4h 05mSouthwest
Deal found 12/17$352
This eDestinos deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/258:25 amMDW - MCO
1 stop7h 17mMultiple Airlines
Sun 1/57:43 amMCO - MDW
2 stops46h 50mMultiple Airlines
Deal found 12/17$404

Find flights from Midway to Orlando within your budget

Customize your flight search to find flights from Midway to Orlando that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Thu 1/23

4:08 pm-12:41 am

1 stop7h 33m

Orlando

Sat 2/15

5:05 am-3:33 pm

1 stop11h 28m

$128

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 1/19

6:10 pm-9:50 pm

Nonstop2h 40m

Orlando

Wed 1/22

7:10 am-9:05 am

Nonstop2h 55m

$164

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 2/18

10:57 am-6:39 pm

1 stop6h 42m

Orlando

Wed 2/26

7:00 am-11:59 am

1 stop5h 59m

$196

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Thu 1/2

6:51 pm-5:16 pm

2 stops21h 25m

Orlando Sanford Intl

Mon 1/6

6:00 am-8:49 am

2 stops27h 49m

$453

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 2/9

4:27 pm-12:41 am

1 stop7h 14m

$64

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 3/2

5:35 am-9:20 am

Nonstop2h 45m

$85

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 2/4

12:44 pm-8:39 pm

1 stop6h 55m

$98

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 1/5

6:51 pm-6:36 pm

2 stops22h 45m

$161

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Thu 1/2

6:51 pm-5:16 pm

2 stops21h 25m

$246

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Thu 3/6

6:26 pm-7:53 pm

2 stops24h 27m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Compare providers for flights from Midway to Orlando

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Orlando in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
GotogatePrice Accuracy2 starsTrust Score*2 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Orlando flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Orlando flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Orlando flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Orlando flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Orlando flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Midway to Orlando

Get recent, data-driven insights about flights from Midway to Orlando including ideal travel times, pricing trends, and more.

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 December 13, 2024.

To ensure you get the cheapest price possible for a flight from Chicago Midway Airport to Orlando, you should look to book at least 88 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 $270). 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 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 December 18, 2024.

It’s typically best to fly out from Chicago Midway Airport to Orlando in the evening. Doing so could potentially save you 30% on the flight price compared to flying at noon, which is usually more expensive.

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 December 16, 2024.

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

Rainfall in Orlando by month

Plan your trip to Orlando by taking into account the average rainfall totals by month.

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.

Temperature in Orlando by month

Plan your trip to Orlando by taking into account the average temperature totals by month.

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).

Reviews of airlines servicing Orlando

Get insights into the airlines that provide service to Orlando. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Orlando. Reviews last updated December 18, 2024.
To help decide which airline to fly from Chicago to Orlando, see what other customers have to say about Frontier and Southwest. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,848 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Southwest
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Delta
8.0
Very good
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Allegiant Air
7.4
Good
829 reviews
Southwest
8.1
Very good
4,848 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Frontier
6.1
Okay
3,479 reviews
Southwest
8.1
Very good
4,848 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

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.

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

    Currently priced at $128, Frontier will fly you from Chicago Midway Airport to Orlando and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Southwest and Delta - these airlines can fly you to your destination from $164 and $196, respectively. Frontier is priced at 56% 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 $64. However, be on the lookout for offers from Southwest and Delta, as they are both options that can get you from Chicago Midway Airport to Orlando for a low price.

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

    Looking at all options, your cheapest flight can be booked for $56. While the most popular route (Chicago Midway - Orlando) can be booked for $108 on average our data indicates $231 when flying from Chicago Midway Airport to Orlando.

  • 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.

  • 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 $270). 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.

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Top 6 airlines flying from Midway to Orlando

Discover the top 6 airlines that operate flights from Midway to Orlando. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$65Average$191FlexibilityNo cancel feeOn-time65%
FrontierCheapest$92Average$219FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$154Average$356FlexibilityNo cancel feeOn-time69%
DeltaCheapest$196Average$356FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$218Average$323FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$252Average$415FlexibilityNo cancel feeOn-time63%
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