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Midway

$92+ 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 6/16. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — MDW
Jun 22 — Jun 291
Mon 6/22
Mon 6/29
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 May 23, 2026.

This Southwest deal was found by Cheapflights users on 5/22. 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.
Tue 8/117:35 am
MCO
-
MDW
Nonstop2h 45m
Southwest
Tue 8/183:30 pm
MDW
-
MCO
Nonstop2h 35m
Southwest
Deal found 5/22$171
This Southwest deal was found by Cheapflights users on 5/22. 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.
Tue 6/162:30 pm
MCO
-
MDW
Nonstop2h 50m
Southwest
Wed 6/243:15 pm
MDW
-
MCO
1 stop4h 10m
Southwest
Deal found 5/22$181
This Kiwi.com deal was found by Cheapflights users on 5/19. 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.
Tue 6/95:10 pm
MCO
-
MDW
1 stop6h 01m
Frontier
Tue 6/1612:27 pm
MDW
-
MCO
1 stop17h 18m
Frontier
Deal found 5/19$183
This Southwest deal was found by Cheapflights users on 5/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:15 pm
MCO
-
MDW
Nonstop3h 00m
Southwest
Wed 6/175:30 pm
MDW
-
MCO
Nonstop2h 45m
Southwest
Deal found 5/20$189
This Expedia deal was found by Cheapflights users on 5/18. 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.
Wed 7/15:25 am
MCO
-
MDW
1 stop6h 44m
Frontier
Wed 7/86:00 am
MDW
-
MCO
1 stop11h 33m
Frontier
Deal found 5/18$190
This Kiwi.com deal was found by Cheapflights users on 5/19. 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.
Tue 7/145:10 pm
MCO
-
MDW
1 stop5h 58m
Frontier
Wed 8/512:11 pm
MDW
-
MCO
1 stop5h 22m
Frontier
Deal found 5/19$192
This Kiwi.com deal was found by Cheapflights users on 5/20. 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.
Thu 9/175:29 pm
MCO
-
MDW
1 stop5h 29m
Frontier
Mon 9/2112:03 pm
MDW
-
MCO
1 stop9h 07m
Frontier
Deal found 5/20$194
This Southwest deal was found by Cheapflights users on 5/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/144:40 pm
MCO
-
MDW
1 stop4h 10m
Southwest
Tue 7/285:30 pm
MDW
-
MCO
Nonstop2h 45m
Southwest
Deal found 5/19$195
This Kiwi.com deal was found by Cheapflights users on 5/18. 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.
Fri 7/2410:59 am
MCO
-
MDW
1 stop4h 39m
Multiple Airlines
Tue 7/2812:11 pm
MDW
-
MCO
1 stop8h 55m
Multiple Airlines
Deal found 5/18$196

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 May 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$171
(Southwest)

One-way from

$92
(Super.com)

Popular in

April

Cheapest in

January

Average price

$298

Good round-trip deal

$297 or less

Good one-way deal

$192 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. 23% potential increase in price ($75 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 23, 2026.
Use the filters below to find and compare flights from Orlando to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 7/28

4:45 pm-10:15 pm

1 stop6h 30m

Chicago Midway

Tue 8/4

9:24 am-2:59 pm

1 stop4h 35m

$197

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 7/21

7:10 am-9:00 am

Nonstop2h 50m

Chicago Midway

Sat 7/25

8:55 am-12:30 pm

Nonstop2h 35m

$313

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 7/22

4:40 pm-7:50 pm

1 stop4h 10m

Chicago Midway

Sat 8/1

7:55 am-1:10 pm

1 stop4h 15m

$324

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 8/6

7:10 am-11:25 am

1 stop5h 15m

Chicago Midway

Fri 8/14

9:10 am-12:45 pm

Nonstop2h 35m

$334

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sun 8/16

8:10 am-12:35 pm

1 stop5h 25m

Chicago Midway

Thu 8/20

5:00 am-8:30 am

Nonstop2h 30m

$334

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 8/1

7:50 am-12:05 pm

1 stop5h 15m

Chicago Midway

Tue 8/4

7:40 am-2:35 pm

2 stops5h 55m

$334
Quickest round-trip

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 6/17

11:00 am-12:45 pm

Nonstop2h 45m

Chicago Midway

Sat 6/20

7:35 pm-11:10 pm

Nonstop2h 35m

$339

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 6/10

6:00 am-12:46 pm

1 stop7h 46m

Chicago Midway

Mon 6/15

5:11 pm-12:59 am

1 stop6h 48m

$345

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 7/3

9:00 am-12:20 pm

1 stop4h 20m

Chicago Midway

Mon 7/6

5:05 pm-11:35 pm

1 stop5h 30m

$347

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 8/20

7:00 am-11:51 am

1 stop5h 51m

Chicago Midway

Sun 8/23

9:24 am-2:59 pm

1 stop4h 35m

$348

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/18

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

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 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, October is the cheapest month in which you can book a flight from Orlando to Chicago Midway Airport (average of $37). Flying from Orlando to Chicago Midway Airport in July is currently the most expensive (average of $120). 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 May 23, 2026.

It’s typically best to fly out from Orlando to Chicago Midway Airport at noon. Doing so could potentially save you 29% on the flight price compared to flying in the morning, which is usually more expensive.

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

How often are flights from Orlando to Chicago delayed?

About 23% of weekly flights between Orlando and Chicago have experienced delays in the past year, with the average delay time being 133 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, Southwest have had the lowest number of delays on this route, with just 23% of flights being delayed.

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

The price you pay for your flight from Orlando to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 75 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 May 23, 2026.

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

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 May 23, 2026.
Read through reviews of airlines operating flights from Orlando to Chicago Midway Airport, such as Southwest,Delta, andFrontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,277 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,277 reviews
Southwest
7.9
Good
4,277 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,444 reviews
Southwest
7.9
Good
4,277 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,940 reviews
Southwest
7.9
Good
4,277 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 2h 50m. There are 990 mi between Orlando and Chicago Midway Airport. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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. Another airline that can offer you cheap pricing is Southwest. Users have found that Frontier is 72% 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 Frontier (76%), Volaris (76%) or Southwest (61%) 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 $302, our data shows the cheapest flight currently is $109. When looking at the most popular route, (Orlando - Chicago Midway), you can expect to pay $171 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, October is the cheapest month in which you can book a flight from Orlando to Chicago Midway Airport (average of $37). Flying from Orlando to Chicago Midway Airport in July is currently the most expensive (average of $120). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Orlando to Midway

Discover the top 2 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 May 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$68Average$163FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$159Average$299FlexibilityNo cancel feeOn-time63%

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