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

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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Oct 19 — Oct 261
Sun 10/19
Sun 10/26
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Orlando are usually found in September or January, booked 81 days in advance, depart on a Thursday or Friday 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 (MCO). 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 September 19, 2025.

Round-trip from

$92
(Frontier)

One-way from

$50
(Priceline)

Popular in

June

Cheapest in

September

Average price

$237

Good round-trip deal

$133 or less

Good one-way deal

$78 or less
From Chicago Midway to Orlando
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One-way flight from Chicago Midway to Orlando
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Highest demand for flights based on searches. 9% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago Midway to Orlando.
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Price to beat on a one-way flight from Chicago Midway to Orlando.
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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 September 19, 2025.

This Frontier deal was found by Cheapflights users on 9/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/205:10 amMDW - MCO
1 stop10h 15mFrontier
Sat 10/258:25 amMCO - MDW
Nonstop2h 56mFrontier
Deal found 9/17$92
This Priceline deal was found by Cheapflights users on 9/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1611:49 amMDW - MCO
Nonstop2h 40mFrontier
Sat 10/188:25 amMCO - MDW
Nonstop2h 56mFrontier
Deal found 9/17$93
This Trip.com deal was found by Cheapflights users on 9/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:30 amMDW - MCO
1 stop7h 37mFrontier
Sat 10/48:30 amMCO - MDW
Nonstop2h 51mFrontier
Deal found 9/16$94
This Mytrip deal was found by Cheapflights users on 9/18. 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.
Sat 10/411:21 amMDW - MCO
Nonstop2h 43mFrontier
Sun 10/57:00 amMCO - MDW
1 stop12h 43mFrontier
Deal found 9/18$100
This CheapOair deal was found by Cheapflights users on 9/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/68:19 amMDW - MCO
Nonstop2h 41mFrontier
Thu 10/97:50 amMCO - MDW
Nonstop2h 57mFrontier
Deal found 9/19$101
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/510:13 amMDW - MCO
Nonstop2h 42mFrontier
Tue 10/77:43 amMCO - MDW
1 stop16h 42mFrontier
Deal found 9/18$103
This Mytrip deal was found by Cheapflights users on 9/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1511:36 amMDW - MCO
Nonstop2h 40mFrontier
Thu 11/202:34 pmMCO - MDW
Nonstop2h 56mFrontier
Deal found 9/17$105
This CheapOair deal was found by Cheapflights users on 9/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/411:21 amMDW - MCO
Nonstop2h 43mFrontier
Sat 10/111:16 pmMCO - MDW
Nonstop2h 55mFrontier
Deal found 9/17$106
This Mytrip deal was found by Cheapflights users on 9/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/19:00 amMDW - MCO
1 stop24h 23mFrontier
Fri 10/37:00 amMCO - MDW
Nonstop2h 53mFrontier
Deal found 9/17$107
This Priceline deal was found by Cheapflights users on 9/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/68:19 amMDW - MCO
Nonstop2h 41mFrontier
Fri 10/102:26 pmMCO - MDW
Nonstop2h 54mFrontier
Deal found 9/16$109
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/108:00 amMDW - MCO
Nonstop2h 41mFrontier
Sat 11/158:30 amMCO - MDW
Nonstop2h 56mFrontier
Deal found 9/16$111
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/36:30 amMDW - MCO
1 stop6h 24mFrontier
Sat 11/88:30 amMCO - MDW
Nonstop2h 56mFrontier
Deal found 9/17$112

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 September 19, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Orlando Airport that are best for you.

Fly from

Midway

Fly to

Orlando

Route

Depart

Return

Price

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 10/4

11:21 am-3:04 pm

Nonstop2h 43m

Orlando

Sat 10/11

1:16 pm-3:11 pm

Nonstop2h 55m

$116

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 10/21

8:05 pm-11:35 pm

Nonstop2h 30m

Orlando

Fri 10/24

6:35 am-8:20 am

Nonstop2h 45m

$158

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 10/14

8:05 pm-11:35 pm

Nonstop2h 30m

Orlando

Fri 10/17

6:35 am-8:20 am

Nonstop2h 45m

$169

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 10/20

5:40 pm-9:15 pm

Nonstop2h 35m

Orlando

Tue 10/21

6:20 pm-10:25 pm

1 stop5h 05m

$188

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 11/15

4:28 pm-10:49 pm

1 stop5h 21m

Orlando

Tue 11/18

5:30 am-9:52 am

1 stop5h 22m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 10/21

1:08 pm-8:37 pm

1 stop6h 29m

Orlando

Wed 10/22

5:30 pm-10:14 pm

1 stop5h 44m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 10/6

5:40 pm-9:15 pm

Nonstop2h 35m

Orlando

Fri 10/10

9:40 pm-11:25 pm

Nonstop2h 45m

$204

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 12/6

1:14 pm-9:28 pm

1 stop7h 14m

Orlando

Mon 12/8

7:52 pm-11:32 pm

1 stop4h 40m

$207

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Thu 12/11

1:25 pm-7:35 pm

1 stop5h 10m

Orlando

Mon 12/15

7:30 am-9:20 am

Nonstop2h 50m

$207

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 10/24

5:52 pm-12:36 am

1 stop5h 44m

Orlando

Sun 10/26

9:00 am-4:42 pm

1 stop8h 42m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/18

Showing 1-10 of 22 results
1
2
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The best insider tips for Chicago Midway Airport to Orlando Airport 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 Airport trip
Airlines
Southwest

Southwest offers free snacks and non-alcoholic drinks, enhancing the short flight experience.


Enjoy free messaging and in-flight entertainment streamed to your device on Southwest flights.

Read more about Southwestby Marisa Garcia
Frontier

Frontier's UpFront Plus seats offer a guaranteed empty middle seat for extra comfort.


Frontier offers Zone 1 boarding with a carry-on purchase or special fare bundle.

Read more about Frontierby Marisa Garcia
Airports
MDW

Use the airport’s mobile system to order food directly to your gate, saving time and ensuring you don't miss boarding.

Read more about MDWby Ramsey Qubein
MCO

Skip car rentals and use rideshares for affordable travel from MCO to Orlando and theme parks.

Read more about MCOby Paul Rubio
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Southwest and Frontier

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
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 Airport

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

Use this chart to determine the optimal time to book a round-trip flight from Midway to Orlando. Price data was last updated on September 12, 2025.

The price you pay for your flight from Chicago Midway Airport to Orlando Airport may vary depending on when you book. For the best chance of a lower fare, look to book 81 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Orlando Airport (average of $206). Flying from Chicago Midway Airport to Orlando Airport 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 MCO?

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 19, 2025.

One of the essential ways to save on airfare from Chicago Midway Airport to Orlando Airport is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 12% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from Midway to Orlando. Price data was last updated on September 14, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Orlando Airport 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.

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 September 19, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines from Chicago Midway Airport to Orlando Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

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
7,964 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

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.
United Airlines
7.4
Good
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

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.
Spirit Airlines
6.3
Okay
8,030 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

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
5.8
Fair
3,171 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

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.

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

    Departing from Chicago Midway Airport to Orlando Airport will take you 2h 30m. Airlines will cover a distance of 990 mi. This flight may include one or multiple stops.

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

    Cheapflights users have booked flights from Chicago Midway Airport to Orlando Airport round-trip from $63. Other airlines that can offer you cheap pricing are Frontier, from $100, and Delta, from $196. These flights start at 78% lower than the current average price 3 months from now.

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

    On average you can expect to pay $189 for a flight from Chicago Midway Airport to Orlando Airport. The cheapest flight overall is $37 while the most popular route, (Chicago Midway - Orlando) is currently priced at $60.

  • 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 Airport?

    Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Orlando Airport (average of $206). Flying from Chicago Midway Airport to Orlando Airport 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

Traveling to a place near Orlando Airport?

Book flights to Orlando Airport if you plan to visit one of these locations
Lake Buena Vista
Sebastian
Sanford
Celebration
Clermont
Lake Mary
Apopka
The Villages
Ormond Beach
DeLand
Altamonte Springs
Orange City
Davenport
Oak Ridge
Lady Lake
Cocoa
Winter Haven
Leesburg
Haines City
Palatka

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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.
O'Hare Intl to Orlando flights
Rockford to Orlando Sanford Intl flights
Midway to Orlando Sanford Intl flights
O'Hare Intl to Orlando Sanford Intl flights

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 September 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$63Average$193FlexibilityNo cancel feeOn-time65%
FrontierCheapest$100Average$214FlexibilityNo cancel feeOn-time62%
DeltaCheapest$196Average$403FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$214Average$394FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$259Average$364FlexibilityNo cancel feeOn-time69%

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