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$50+ 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 12/21. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — MDW
Dec 12 — Dec 191
Fri 12/12
Fri 12/19
1 adult, Economy
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Cheapflights Tip: The best prices from Orlando to Chicago Midway are usually found in January or February, booked 13 days in advance, depart on a Friday or Thursday and return on a Thursday

Cheap 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 November 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$77
(Kiwi.com)

One-way from

$50
(Priceline)

Popular in

June

Cheapest in

January

Average price

$248

Good round-trip deal

$98 or less

Good one-way deal

$95 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.
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From Orlando (ORL) to Chicago Midway
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One-way flight from Orlando (ORL) to Chicago Midway
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($54 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 November 2025
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

Find 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 November 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/257:58 pmMCO - MDW
Nonstop3h 00mFrontier
Mon 12/293:10 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 11/11$77
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/217:04 pmMCO - MDW
Nonstop3h 00mFrontier
Mon 12/293:10 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 11/11$78
This CheapOair deal was found by Cheapflights users on 11/9. 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.
Sun 11/232:34 pmMCO - MDW
Nonstop2h 56mFrontier
Thu 11/275:30 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 11/9$79
This Frontier deal was found by Cheapflights users on 11/11. 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 11/223:10 pmMCO - MDW
Nonstop2h 57mFrontier
Wed 11/265:30 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 11/11$80
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/128:40 pmMCO - MDW
Nonstop2h 59mFrontier
Mon 12/153:52 pmMDW - MCO
1 stop6h 49mFrontier
Deal found 11/11$83
This Super.com deal was found by Cheapflights users on 11/11. 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 12/117:58 pmMCO - MDW
Nonstop3h 00mFrontier
Sat 12/136:00 amMDW - MCO
1 stop5h 28mFrontier
Deal found 11/11$84
This Trip.com deal was found by Cheapflights users on 11/10. 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 12/47:58 pmMCO - MDW
Nonstop3h 00mFrontier
Sun 12/76:37 pmMDW - MCO
Nonstop2h 46mFrontier
Deal found 11/10$85
This Priceline deal was found by Cheapflights users on 11/12. 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 12/45:30 amMCO - MDW
1 stop9h 34mFrontier
Fri 12/123:52 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 11/12$88
This CheapOair deal was found by Cheapflights users on 11/12. 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.
Fri 12/58:40 pmMCO - MDW
Nonstop2h 59mFrontier
Mon 12/812:18 pmMDW - MCO
1 stop16h 13mFrontier
Deal found 11/12$89
This Mytrip deal was found by Cheapflights users on 11/10. 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.
Thu 12/47:58 pmMCO - MDW
Nonstop3h 00mFrontier
Mon 12/812:18 pmMDW - MCO
1 stop16h 13mFrontier
Deal found 11/10$90
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 11/242:56 pmMCO - MDW
Nonstop2h 56mFrontier
Fri 11/284:46 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 11/9$91

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 November 12, 2025.
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

Thu 12/4

7:58 pm-9:58 pm

Nonstop3h 00m

Chicago Midway

Mon 12/8

12:18 pm-5:31 am

1 stop16h 13m

$90

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 1/15

8:35 pm-10:25 pm

Nonstop2h 50m

Chicago Midway

Tue 1/20

3:15 pm-6:50 pm

Nonstop2h 35m

$137

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 12/17

9:30 am-11:20 am

Nonstop2h 50m

Chicago Midway

Wed 12/31

5:05 am-8:40 am

Nonstop2h 35m

$147

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 11/19

10:40 am-11:42 am

1 stop26h 02m

Chicago Midway

Sun 11/23

5:30 pm-9:18 pm

Nonstop2h 48m

$157

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 12/10

2:45 pm-4:35 pm

Nonstop2h 50m

Chicago Midway

Wed 12/17

9:30 am-1:10 pm

Nonstop2h 40m

$157

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 12/13

8:45 pm-10:35 pm

Nonstop2h 50m

Chicago Midway

Sun 12/14

7:35 pm-11:10 pm

Nonstop2h 35m

$158

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 1/22

11:50 am-1:45 pm

Nonstop2h 55m

Chicago Midway

Sun 1/25

5:30 am-9:15 am

Nonstop2h 45m

$167

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 12/10

4:35 pm-6:25 pm

Nonstop2h 50m

Chicago Midway

Sun 12/14

7:35 pm-11:10 pm

Nonstop2h 35m

$169

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 12/11

6:50 pm-8:40 pm

Nonstop2h 50m

Chicago Midway

Sat 12/13

11:00 am-2:35 pm

Nonstop2h 35m

$178

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 12/5

4:35 pm-6:25 pm

Nonstop2h 50m

Chicago Midway

Mon 12/8

5:05 am-8:40 am

Nonstop2h 35m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 17 results
1
2

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Orlando-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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

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

Use this chart to determine the optimal time to book a round-trip flight from Orlando to Midway. Price data was last updated on November 7, 2025.

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 13 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 Orlando to Chicago Midway Airport?

Currently, February is the cheapest month in which you can book a flight from Orlando to Chicago Midway Airport (average of $55). Flying from Orlando to Chicago Midway Airport in March is currently the most expensive (average of $165). 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 November 12, 2025.

It’s typically best to fly out from Orlando to Chicago Midway Airport at noon. Doing so could potentially save you 17% 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 November 2, 2025.

Travelers seeking maximum savings on their Orlando to Chicago Midway Airport flight should consider departing on Wednesday 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 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 November 12, 2025.
Read through reviews of airlines operating flights from Orlando to Chicago Midway Airport, such as Southwest, Delta, and Spirit Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,235 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

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
4,235 reviews
Southwest
8.0
Very good
4,235 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

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
8,008 reviews
Southwest
8.0
Very good
4,235 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

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.
Spirit Airlines
6.3
Okay
8,137 reviews
Southwest
8.0
Very good
4,235 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

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
5.8
Fair
3,113 reviews
Southwest
8.0
Very good
4,235 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

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 2h 50m. 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 Spirit Airlines, from $88, and Delta, from $114. Users have found that Frontier is 68% cheaper than the other options available to this destination.

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

    While on average a flight from Orlando to Chicago Midway Airport is generally $147, our data shows the cheapest flight currently is $42. When looking at the most popular route, (Orlando - Chicago Midway), you can expect to pay $70 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, February is the cheapest month in which you can book a flight from Orlando to Chicago Midway Airport (average of $55). Flying from Orlando to Chicago Midway Airport in March is currently the most expensive (average of $165). 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
Hammond
Porter
Benton Harbor
Merrillville

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Top 4 airlines flying from Orlando to Midway

Discover the top 4 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 November 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$68Average$165FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$88Average$120FlexibilityNo cancel feeOn-time65%
DeltaCheapest$114Average$216FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$159Average$321FlexibilityNo cancel feeOn-time63%

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