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$57+ 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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Apr 22 — Apr 291
Wed 4/22
Wed 4/29
1 adult, Economy
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Find cheap flights from Midway to Orlando with Cheapflights

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Cheapflights Tip: The best prices from Chicago Midway to Orlando are usually found in February or January, booked 28 days in advance, depart on a Thursday or Friday and return on a Friday

Cheap 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 March 23, 2026.

This Frontier deal was found by Cheapflights users on 3/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/179:14 am
MDW
-
MCO
Nonstop2h 49m
Frontier
Fri 4/243:55 pm
MCO
-
MDW
Nonstop2h 59m
Frontier
Deal found 3/18$124
This Frontier deal was found by Cheapflights users on 3/20. 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.
Sat 5/29:14 am
MDW
-
MCO
Nonstop2h 49m
Frontier
Sun 5/35:45 am
MCO
-
MDW
Nonstop2h 56m
Frontier
Deal found 3/20$126
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/189:14 am
MDW
-
MCO
Nonstop2h 49m
Frontier
Sun 4/196:00 am
MCO
-
MDW
Nonstop2h 59m
Frontier
Deal found 3/19$127
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/189:14 am
MDW
-
MCO
Nonstop2h 49m
Frontier
Wed 4/222:40 pm
MCO
-
MDW
1 stop5h 51m
Frontier
Deal found 3/19$128
This Expedia deal was found by Cheapflights users on 3/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/55:05 am
MDW
-
MCO
Nonstop2h 46m
Frontier
Sat 4/119:05 pm
MCO
-
MDW
Nonstop3h 00m
Frontier
Deal found 3/21$129
This Kiwi.com deal was found by Cheapflights users on 3/18. 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.
Sat 4/189:14 am
MDW
-
MCO
Nonstop2h 49m
Multiple Airlines
Fri 4/246:22 am
MCO
-
MDW
1 stop17h 04m
Multiple Airlines
Deal found 3/18$130
This Kiwi.com deal was found by Cheapflights users on 3/18. 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.
Mon 4/65:30 am
MDW
-
MCO
Nonstop2h 46m
Multiple Airlines
Wed 4/88:25 am
MCO
-
MDW
1 stop14h 54m
Multiple Airlines
Deal found 3/18$132
This Expedia deal was found by Cheapflights users on 3/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:00 am
MDW
-
MCO
Nonstop2h 48m
Frontier
Thu 4/166:05 am
MCO
-
MDW
Nonstop2h 59m
Frontier
Deal found 3/18$134
This Expedia deal was found by Cheapflights users on 3/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/189:14 am
MDW
-
MCO
Nonstop2h 49m
Frontier
Tue 4/212:40 pm
MCO
-
MDW
1 stop5h 51m
Frontier
Deal found 3/21$135
This Trip.com deal was found by Cheapflights users on 3/20. 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.
Wed 4/226:15 am
MDW
-
MCO
1 stop6h 19m
Frontier
Sat 4/252:13 pm
MCO
-
MDW
Nonstop3h 00m
Frontier
Deal found 3/20$136
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 4/55:05 am
MDW
-
MCO
Nonstop2h 46m
Frontier
Thu 4/97:22 pm
MCO
-
MDW
Nonstop2h 59m
Frontier
Deal found 3/20$137

Find 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 March 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$124
(Frontier)

One-way from

$57
(Trip.com)

Popular in

June

Cheapest in

February

Average price

$307

Good round-trip deal

$204 or less

Good one-way deal

$119 or less
Provider with most accurate pricing for Chicago Midway-Orlando flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Orlando flights.
Search Deals
From Chicago Midway to Orlando
Search Deals
One-way flight from Chicago Midway to Orlando
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Orlando.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Orlando.
Search Deals

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 March 23, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Orlando Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 4/24

8:35 pm-12:10 am

Nonstop2h 35m

Orlando

Tue 4/28

7:35 pm-9:25 pm

Nonstop2h 50m

$287

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 4/11

5:25 pm-9:05 pm

Nonstop2h 40m

Orlando

Tue 4/14

7:15 am-9:10 am

Nonstop2h 55m

$287

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 4/17

4:35 pm-8:15 pm

Nonstop2h 40m

Orlando

Mon 4/20

7:30 pm-11:30 pm

1 stop5h 00m

$287

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 5/16

3:35 pm-9:20 pm

1 stop4h 45m

Orlando

Sun 5/17

9:10 am-11:00 am

Nonstop2h 50m

$293

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 5/6

1:55 pm-7:20 pm

1 stop4h 25m

Orlando

Mon 5/11

8:15 am-1:05 pm

1 stop5h 50m

$312

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Thu 4/16

8:35 pm-12:10 am

Nonstop2h 35m

Orlando

Thu 4/23

10:10 am-12:00 pm

Nonstop2h 50m

$318

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Thu 5/28

7:55 am-1:20 pm

1 stop4h 25m

Orlando

Sat 5/30

8:45 pm-10:35 pm

Nonstop2h 50m

$346

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 5/20

6:20 pm-9:55 pm

Nonstop2h 35m

Orlando

Sun 5/24

8:55 pm-10:45 pm

Nonstop2h 50m

$347

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Thu 5/7

1:22 pm-7:39 pm

1 stop5h 17m

Orlando

Sun 5/10

5:30 am-10:00 am

1 stop5h 30m

$358

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 5/23

3:35 pm-9:20 pm

1 stop4h 45m

Orlando

Sun 5/31

6:35 pm-8:30 pm

Nonstop2h 55m

$414

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/20

Showing 1-10 of 23 resultsSorted by cheapest first
1
2
3

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*2 stars
OvagoPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
Super.comPrice Accuracy-Trust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
JustAirTicketPrice 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 Airport 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 Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Orlando Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Orlando Airport 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 Airport 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.

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 March 13, 2026.

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 28 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Orlando Airport (average of $58). Flying from Chicago Midway Airport to Orlando Airport in June is currently the most expensive (average of $166). 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 March 23, 2026.

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 10% 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 March 23, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to Orlando Airport flight should consider departing on Monday at noon 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.

The best insider tips for Chicago Midway Airport to Orlando Airport flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Orlando Airport trip
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Frontier and Southwest

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

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

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

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 March 23, 2026.
See what other customers who have flown with Southwest,Delta, andFrontier 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
4,324 reviews

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Southwest
8.0
Very good
4,324 reviews
Southwest
8.0
Very good
4,324 reviews

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Delta
7.9
Good
8,318 reviews
Southwest
8.0
Very good
4,324 reviews

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Frontier
5.7
Fair
3,020 reviews
Southwest
8.0
Very good
4,324 reviews

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

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 35m. Airlines will cover a distance of 990 mi. All flights are typically nonstop.

  • 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 $70. Other airlines that can offer you cheap pricing are Delta, from $98, and Southwest, from $197. These flights start at 74% lower than the current average price 3 months from now.

  • What are the most reliable airlines from Chicago Midway Airport to Orlando Airport?

    The top 3 most reliable airlines when flying from Chicago Midway Airport to Orlando Airport are Frontier (83%), Volaris (66%) and Southwest (63%).

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

    On average you can expect to pay $238 for a flight from Chicago Midway Airport to Orlando Airport. The cheapest flight overall is $57 while the most popular route, (Chicago Midway - Orlando) is currently priced at $140.

  • 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Orlando Airport (average of $58). Flying from Chicago Midway Airport to Orlando Airport in June is currently the most expensive (average of $166). 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
Clermont
Celebration
Sanford
Altamonte Springs
Sebastian
Winter Haven
Apopka
Orange City
Lake Mary
Titusville
Leesburg
Four Corners
Cocoa
Davenport
Lady Lake
Haines City
Palatka
The Villages
Belle Isle

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

Top 3 airlines flying from Midway to Orlando

Discover the top 3 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 March 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$70Average$194FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$533FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$197Average$383FlexibilityNo cancel feeOn-time63%

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