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Midway

$55+ Cheap flights from Orlando (ORL) to Midway (MDW)

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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — MDW
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Orlando to Midway

Cheapest flights from Orlando to Midway
Explore the most affordable flight options available from Orlando to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Super.com deal was found by Cheapflights users on 1/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/711:05 am
MCO
-
MDW
Nonstop3h 03m
Frontier
Tue 3/1011:19 am
MDW
-
MCO
Nonstop2h 45m
Frontier
Deal found 1/28$91
This Frontier deal was found by Cheapflights users on 1/27. 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.
Thu 2/55:49 pm
MCO
-
MDW
Nonstop3h 03m
Frontier
Mon 2/97:00 pm
MDW
-
MCO
Nonstop2h 48m
Frontier
Deal found 1/27$94
This Super.com deal was found by Cheapflights users on 1/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2012:20 pm
MCO
-
MDW
Nonstop3h 06m
Frontier
Sun 2/227:30 am
MDW
-
MCO
Nonstop2h 50m
Frontier
Deal found 1/28$97
This CheapOair deal was found by Cheapflights users on 1/26. 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.
Thu 2/1912:20 pm
MCO
-
MDW
Nonstop3h 06m
Frontier
Sun 2/227:30 am
MDW
-
MCO
Nonstop2h 50m
Frontier
Deal found 1/26$98
This Trip.com deal was found by Cheapflights users on 1/27. 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 2/2612:20 pm
MCO
-
MDW
Nonstop3h 06m
Frontier
Mon 3/29:22 pm
MDW
-
MCO
Nonstop2h 47m
Frontier
Deal found 1/27$99
This Trip.com deal was found by Cheapflights users on 1/26. 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 2/2612:20 pm
MCO
-
MDW
Nonstop3h 06m
Frontier
Sat 3/72:56 pm
MDW
-
MCO
Nonstop2h 46m
Frontier
Deal found 1/26$101
This Super.com deal was found by Cheapflights users on 1/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2612:20 pm
MCO
-
MDW
Nonstop3h 06m
Frontier
Thu 3/57:30 am
MDW
-
MCO
Nonstop2h 50m
Frontier
Deal found 1/27$105
This Super.com deal was found by Cheapflights users on 1/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1212:20 pm
MCO
-
MDW
Nonstop3h 06m
Frontier
Thu 2/197:30 am
MDW
-
MCO
Nonstop2h 50m
Frontier
Deal found 1/27$106
This Frontier deal was found by Cheapflights users on 1/27. 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.
Thu 2/1212:20 pm
MCO
-
MDW
Nonstop3h 06m
Frontier
Mon 2/169:22 pm
MDW
-
MCO
Nonstop2h 47m
Frontier
Deal found 1/27$112
This Frontier deal was found by Cheapflights users on 1/28. 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.
Wed 2/1810:28 am
MCO
-
MDW
1 stop9h 39m
Frontier
Sun 2/227:30 am
MDW
-
MCO
Nonstop2h 50m
Frontier
Deal found 1/28$113
This Frontier deal was found by Cheapflights users on 1/27. 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.
Thu 4/166:05 am
MCO
-
MDW
Nonstop2h 59m
Frontier
Mon 4/209:14 am
MDW
-
MCO
Nonstop2h 49m
Frontier
Deal found 1/27$114
This Trip.com deal was found by Cheapflights users on 1/27. 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.
Fri 2/1312:20 pm
MCO
-
MDW
Nonstop3h 06m
Frontier
Mon 3/169:51 pm
MDW
-
MCO
Nonstop2h 47m
Frontier
Deal found 1/27$117

Find flight deals from Orlando to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Orlando (ORL) to Midway (MDW). 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$91
(Super.com)

One-way from

$55
(Expedia)

Popular in

June

Cheapest in

January

Average price

$92

Good round-trip deal

$127 or less

Good one-way deal

$145 or less
Provider with most accurate pricing for Orlando (ORL)-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Orlando (ORL)-Chicago Midway flights.
Search Deals
From Orlando (ORL) to Chicago Midway
Search Deals
One-way flight from Orlando (ORL) to Chicago Midway
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Orlando (ORL) to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Orlando (ORL) to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Orlando to Midway 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 January 29, 2026.
Use the filters below to find and compare flights from Orlando to Chicago Midway Airport that are best for you.

Fly from

Orlando

Fly to

Midway

Route

Depart

Return

Price

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 3/13

9:51 pm-11:51 pm

Nonstop3h 00m

Chicago Midway

Wed 3/18

11:19 am-3:04 pm

Nonstop2h 45m

$97

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 3/6

11:05 am-1:08 pm

Nonstop3h 03m

Chicago Midway

Sun 3/8

11:00 am-2:45 pm

Nonstop2h 45m

$98

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 2/18

10:28 am-7:07 pm

1 stop9h 39m

Chicago Midway

Sun 2/22

7:30 am-11:20 am

Nonstop2h 50m

$113

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 2/27

12:20 pm-2:26 pm

Nonstop3h 06m

Chicago Midway

Sat 2/28

9:15 am-6:00 pm

1 stop7h 45m

$124

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 2/27

8:36 pm-3:19 pm

1 stop19h 43m

Chicago Midway

Mon 3/2

9:22 pm-1:09 am

Nonstop2h 47m

$124

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 3/3

10:28 am-7:07 pm

1 stop9h 39m

Chicago Midway

Wed 3/4

7:15 am-3:04 pm

1 stop6h 49m

$128

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 4/17

6:05 am-8:04 am

Nonstop2h 59m

Chicago Midway

Mon 4/20

9:14 am-1:03 pm

Nonstop2h 49m

$136

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 2/14

12:49 pm-2:55 pm

Nonstop3h 06m

Chicago Midway

Mon 2/16

9:22 pm-1:09 am

Nonstop2h 47m

$137

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 2/13

12:20 pm-2:26 pm

Nonstop3h 06m

Chicago Midway

Mon 2/16

6:00 am-7:31 am

1 stop24h 31m

$139

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 2/20

12:20 pm-2:26 pm

Nonstop3h 06m

Chicago Midway

Sun 2/22

3:00 pm-11:40 pm

1 stop7h 40m

$174

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 21 results
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2
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Compare providers for flights from Orlando to Midway

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 Orlando to Midway in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust 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 Orlando-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Orlando-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Orlando-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Orlando-Chicago Midway 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 Orlando-Chicago Midway 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 Orlando to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Orlando 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 Orlando to Chicago Midway Airport

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

Currently, January is the cheapest month in which you can book a flight from Orlando to Chicago Midway Airport (average of $59). Flying from Orlando to Chicago Midway Airport in March is currently the most expensive (average of $173). 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 ORL to MDW?

Find hourly flight availability from Orlando to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 29, 2026.

It’s typically best to fly out from Orlando to Chicago Midway Airport at noon. Doing so could potentially save you 27% on the flight price compared to flying in the morning, which is usually more expensive.

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

Use this chart to determine the cheapest time to fly round-trip from Orlando to Midway. Price data was last updated on January 24, 2026.

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

How often are flights from Orlando to Chicago delayed?

About 20% of weekly flights between Orlando and Chicago have experienced delays in the past year, with the average delay time being 134 minutes.

What is the most punctual flight time for Orlando to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Orlando to Chicago flights?

Over the last year, Frontier have had the lowest number of delays on this route, with just 18% of flights being delayed.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated January 29, 2026.
Read through reviews of airlines operating flights from Orlando to Chicago Midway Airport, such as Southwest, Delta, and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,267 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Delta
7.9
Good
8,125 reviews
Southwest
8.0
Very good
4,267 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Frontier
5.7
Fair
3,056 reviews
Southwest
8.0
Very good
4,267 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Orlando to Midway. 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 Orlando to Chicago Midway Airport?

    Departing from Orlando to Chicago Midway Airport will take you 3h. There are 990 mi between Orlando and Chicago Midway Airport. Most flights are nonstop.

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

    Cheapflights users have booked flights from Orlando to Chicago Midway Airport round-trip from $68. Other airlines that can offer you cheap pricing are Delta, from $114, and Southwest, from $159. Users have found that Frontier is 69% cheaper than the other options available to this destination.

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

    No one likes to see their flight delayed. When booking a flight from Orlando to Chicago Midway Airport consider choosing Southwest (77%), Volaris (64%) or Frontier (63%) as they are the most reliable in getting you off to your destination on time.

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

    While on average a flight from Orlando to Chicago Midway Airport is generally $215, our data shows the cheapest flight currently is $66. When looking at the most popular route, (Orlando - Chicago Midway), you can expect to pay $98 for that flight.

  • Can I find deals for flights from Orlando to Midway that include hotel bookings?

    Yes. In addition to deals on Orlando to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Orlando to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Orlando to Midway.

  • Can I find deals for business class flights from Orlando to Midway?

    Yes. Cheapflights offers flight deals from Orlando to Midway 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 Orlando to Chicago Midway Airport?

    Currently, January is the cheapest month in which you can book a flight from Orlando to Chicago Midway Airport (average of $59). Flying from Orlando to Chicago Midway Airport in March is currently the most expensive (average of $173). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Orlando to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Orlando to Midway

Discover the top 3 airlines that operate flights from Orlando to Midway. 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$68Average$158FlexibilityNo cancel feeOn-time62%
DeltaCheapest$114Average$196FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$159Average$294FlexibilityNo cancel feeOn-time63%

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