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$63+ 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ORL
Apr 20 — Apr 271
Sun 4/20
Sun 4/27
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Orlando are usually found in September or August, booked 31 days in advance, depart on a Saturday or Thursday 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 April 15, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$126
(Cheapflightsfares)

One-way from

$64
(CheapOair)

Popular in

December

Cheapest in

September

Average price

$218

Good round-trip deal

$207 or less

Good one-way deal

$102 or less
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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Highest demand for flights based on searches. 17% potential increase in price ($51 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Chicago Midway to Orlando (ORL).
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Price to beat on a one-way flight from Chicago Midway to Orlando (ORL).
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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 April 15, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/91:19 pmMDW - MCO
Nonstop2h 44mFrontier
Sun 5/113:33 pmMCO - MDW
Nonstop2h 57mFrontier
Deal found 4/14$125
This Southwest deal was found by Cheapflights users on 4/14. 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.
Wed 5/147:55 pmMDW - MCO
Nonstop2h 35mSouthwest
Wed 5/216:25 pmMCO - MDW
Nonstop2h 50mSouthwest
Deal found 4/14$177
This Delta deal was found by Cheapflights users on 4/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/146:00 amMDW - MCO
1 stop4h 45mDelta
Wed 5/143:45 pmMCO - MDW
1 stop6h 43mDelta
Deal found 4/14$191
This Mytrip deal was found by Cheapflights users on 4/14. 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.
Mon 6/27:00 pmMDW - SFB
1 stop14h 35mAllegiant Air
Thu 6/510:04 pmSFB - MDW
1 stop16h 59mAllegiant Air
Deal found 4/14$210

Cheapflights Fare Finder

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 April 15, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Orlando that are best for you.

Fly from

Midway

Fly to

Orlando

Route

Depart

Return

Price

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 5/9

1:19 pm-5:03 pm

Nonstop2h 44m

Orlando

Sun 5/11

3:33 pm-5:30 pm

Nonstop2h 57m

$125

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 5/14

7:55 pm-11:30 pm

Nonstop2h 35m

Orlando

Wed 5/21

6:25 pm-8:15 pm

Nonstop2h 50m

$177

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 5/14

6:00 am-11:45 am

1 stop4h 45m

Orlando

Wed 5/14

3:45 pm-9:28 pm

1 stop6h 43m

$191

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Mon 6/2

7:00 pm-10:35 am

1 stop14h 35m

Orlando Sanford Intl

Thu 6/5

10:04 pm-2:03 pm

1 stop16h 59m

$210

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 5/19

9:42 am-8:11 am

2 stops21h 29m

Orlando

Fri 5/23

8:30 am-2:04 pm

1 stop6h 34m

$286

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 5/2

1:19 pm-5:03 pm

Nonstop2h 44m

$63

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 5/14

7:10 am-10:40 am

Nonstop2h 30m

$89

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 5/14

6:00 am-11:45 am

1 stop4h 45m

$99

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Fri 5/30

7:00 pm-8:48 pm

1 stop24h 48m

$102

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 5/30

8:04 pm-9:17 am

1 stop12h 13m

$103

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/14

Showing 1-10 of 11 results
1
2

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy1 starTrust Score*2 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
FlightnetworkPrice Accuracy-Trust Score*3 stars
GotogatePrice Accuracy3 starsTrust Score*2 stars
JustAirTicketPrice Accuracy-Trust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*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 eDreams the most. eDreams 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.

The best insider tips for Chicago Midway Airport to Orlando flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Orlando trip
Airports
MDW

Use the Orange Line train for a quick, affordable ride to MDW, taking less than 30 minutes from downtown Chicago.

Read more about MDWby Ramsey Qubein
MCO

Skip the rental car at MCO and opt for rideshare to explore Orlando, as it's often cheaper and more convenient.

Read more about MCOby Paul Rubio
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Paul Rubio

Paul Rubio

Expert on MCO

Paul Rubio

Paul Rubio

Travel journalist and photographer Paul Rubio is a Miami native (and current resident), who has lived in nine countries and traveled to 137. He is an expert in luxury travel, eco-travel, loyalty programs, hotels, airports and airlines. He is a contributing editor at AFAR, Condé Nast Traveler, LUXURY Magazine, and Palm Beach Illustrated.

Read more

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.

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 April 11, 2025.

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 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 April 15, 2025.

It’s typically best to fly out from Chicago Midway Airport to Orlando in the evening. Doing so could potentially save you 14% on the flight price compared to flying in the morning, 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 March 30, 2025.

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. 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 April 15, 2025.
To help decide which airline to fly from Chicago to Orlando, see what other customers have to say about Southwest, Delta and Allegiant Air. 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
8.0
Very good
4,279 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

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
8.0
Very good
4,279 reviews
Southwest
8.0
Very good
4,279 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

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
7,917 reviews
Southwest
8.0
Very good
4,279 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

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
7.3
Good
734 reviews
Southwest
8.0
Very good
4,279 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

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
6.0
Okay
3,281 reviews
Southwest
8.0
Very good
4,279 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

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 $126, 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 $177 and $198, respectively. Frontier is priced at 47% 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 $62. While the most popular route (Chicago Midway - Orlando) can be booked for $126 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 $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.

See more FAQs

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Alternative routes for Midway to Orlando

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Midway to Orlando

Discover the top 5 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 April 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$103Average$221FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$111Average$191FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$351FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$247Average$425FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$259Average$397FlexibilityNo cancel feeOn-time69%

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