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$108+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Sep 3 — Sep 101
Thu 9/3
Thu 9/10
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 January or February, booked 80 days in advance, depart on a Thursday or Sunday 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 August 4, 2026.

This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Wed 11/117:25 am
MDW
-
MCO
1 stop8h 56m
Frontier
Tue 11/1712:52 pm
MCO
-
MDW
1 stop10h 01m
Frontier
Deal found 8/2$186
This Kiwi.com deal was found by Cheapflights users on 7/31. 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.
Wed 11/117:25 am
MDW
-
MCO
1 stop8h 56m
Frontier
Mon 11/167:10 am
MCO
-
MDW
1 stop28h 48m
Frontier
Deal found 7/31$202
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Tue 9/156:25 am
MDW
-
MCO
1 stop9h 44m
Frontier
Tue 9/2212:50 pm
MCO
-
MDW
1 stop5h 56m
Frontier
Deal found 7/30$214
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 11/1412:03 pm
MDW
-
MCO
1 stop9h 07m
Frontier
Wed 11/185:29 pm
MCO
-
MDW
1 stop5h 24m
Frontier
Deal found 7/31$218
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Tue 9/226:25 am
MDW
-
MCO
1 stop9h 44m
Frontier
Tue 9/2912:50 pm
MCO
-
MDW
1 stop5h 56m
Frontier
Deal found 7/30$219
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 8/1711:06 am
MDW
-
MCO
1 stop7h 51m
Frontier
Fri 8/2110:03 am
MCO
-
MDW
1 stop25h 47m
Frontier
Deal found 7/30$221
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 8/1711:06 am
MDW
-
MCO
1 stop7h 51m
Frontier
Thu 8/205:23 pm
MCO
-
MDW
1 stop6h 24m
Frontier
Deal found 7/30$223
This Expedia deal was found by Cheapflights users on 7/31. 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.
Mon 12/78:07 pm
MDW
-
MCO
Nonstop2h 50m
Frontier
Mon 12/145:01 pm
MCO
-
MDW
Nonstop3h 01m
Frontier
Deal found 7/31$224
This Kiwi.com deal was found by Cheapflights users on 7/31. 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.
Thu 8/2011:50 am
MDW
-
MCO
1 stop9h 24m
Frontier
Mon 8/245:23 pm
MCO
-
MDW
1 stop6h 24m
Frontier
Deal found 7/31$226
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 8/2911:45 am
MDW
-
MCO
1 stop7h 15m
Frontier
Thu 9/35:23 pm
MCO
-
MDW
1 stop6h 24m
Frontier
Deal found 7/30$227
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Thu 8/2711:50 am
MDW
-
MCO
1 stop7h 10m
Frontier
Thu 9/35:23 pm
MCO
-
MDW
1 stop6h 24m
Frontier
Deal found 7/30$228

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 August 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$186
(Kiwi.com)

One-way from

$108
(Kiwi.com)

Popular in

July

Cheapest in

January

Average price

$347

Good round-trip deal

$328 or less

Good one-way deal

$179 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. 27% potential increase in price ($119 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 August 4, 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

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 9/30

6:20 pm-10:05 pm

Nonstop2h 45m

Orlando

Sat 10/3

7:25 pm-9:15 pm

Nonstop2h 50m

$237

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 9/2

3:40 pm-7:15 pm

Nonstop2h 35m

Orlando

Fri 9/11

10:20 am-1:45 pm

1 stop4h 25m

$253

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 9/8

6:20 pm-10:05 pm

Nonstop2h 45m

Orlando

Fri 9/11

10:20 am-1:45 pm

1 stop4h 25m

$253

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 9/9

3:40 pm-7:20 pm

Nonstop2h 40m

Orlando

Sat 9/12

7:05 am-8:55 am

Nonstop2h 50m

$257

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 9/16

6:20 pm-10:05 pm

Nonstop2h 45m

Orlando

Wed 9/23

3:05 pm-7:35 pm

1 stop5h 30m

$263

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Thu 10/29

1:27 pm-7:39 pm

1 stop5h 12m

Orlando

Tue 11/3

4:40 pm-10:33 pm

1 stop6h 53m

$277

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Thu 9/24

1:19 pm-9:13 pm

1 stop6h 54m

Orlando

Mon 9/28

6:40 pm-10:44 pm

1 stop5h 04m

$298
Quickest round-trip

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 8/30

6:00 pm-9:40 pm

Nonstop2h 40m

Orlando

Tue 9/1

1:00 pm-2:45 pm

Nonstop2h 45m

$303

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Thu 9/24

7:50 pm-11:25 pm

Nonstop2h 35m

Orlando

Mon 9/28

6:55 am-8:45 am

Nonstop2h 50m

$303

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Thu 9/3

5:10 pm-1:04 am

1 stop6h 54m

Orlando

Mon 9/7

6:15 am-9:59 am

1 stop4h 44m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 22 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 August.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
OvagoPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars
Super.comPrice Accuracy-Trust Score*3 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 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?

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 79 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 $197). Flying from Chicago Midway Airport to Orlando Airport in July is currently the most expensive (average of $497). 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 August 4, 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 at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 16% 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 August 1, 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. Wednesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Chicago Midway Airport to Orlando Airport?

Airfare is below average for this route at the moment.

Chicago Midway Airport to Orlando Airport flights typically cost between $283 and $533 in November.
The cheapest round-trip price found within the last 5 days was $186 on Frontier (Nov 11-Nov 17).

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 Southwest and Frontier

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 August 4, 2026.
See what other customers who have flown with Southwest and Frontier 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
4,221 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

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
4,221 reviews
Southwest
8.0
Very good
4,221 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

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
5.6
Fair
2,736 reviews
Southwest
8.0
Very good
4,221 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

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 45m. 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 $66. Another airline that can offer you cheap pricing is Southwest. These flights start at 79% 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 $328 for a flight from Chicago Midway Airport to Orlando Airport. The cheapest flight overall is $108 while the most popular route, (Chicago Midway - Orlando) is currently priced at $237.

  • 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 $197). Flying from Chicago Midway Airport to Orlando Airport in July is currently the most expensive (average of $497). 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
Titusville
Celebration
Winter Haven
Four Corners
River Ranch
Leesburg
Sebastian
Sanford
Apopka
Ormond Beach
Daytona Beach Shores
Lake Mary
Clermont
Flagler Beach
Cocoa
Altamonte Springs
The Villages
Davenport
Haines City

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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 2 airlines flying from Midway to Orlando

Discover the top 2 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 August 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$66Average$202FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$208Average$420FlexibilityNo cancel feeOn-time63%

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