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Midway

$53+ Cheap flights from Orlando (MCO) 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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Aug 18 — Aug 251
Mon 8/18
Mon 8/25
1 adult, Economy
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Cheapflights Tip: The best prices from Orlando to Chicago Midway are usually found in February or October, booked 69 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 (MCO) 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 August 13, 2025.

Round-trip from

$98
(CheapOair)

One-way from

$53
(Cheapflightsfares)

Popular in

March

Cheapest in

February

Average price

$207

Good round-trip deal

$163 or less

Good one-way deal

$96 or less
From Orlando to Chicago Midway
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One-way flight from Orlando to Chicago Midway
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Highest demand for flights based on searches. 0% potential increase in price ($2 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Orlando to Chicago Midway.
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Price to beat on a one-way flight from Orlando to Chicago Midway.
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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 August 13, 2025.

This CheapOair deal was found by Cheapflights users on 8/12. 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 9/267:00 amMCO - MDW
Nonstop2h 53mFrontier
Mon 9/298:19 amMDW - MCO
Nonstop2h 41mFrontier
Deal found 8/12$98
This Frontier deal was found by Cheapflights users on 8/13. 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 11/65:50 amMCO - MDW
Nonstop2h 54mFrontier
Sun 11/98:39 amMDW - MCO
Nonstop2h 41mFrontier
Deal found 8/13$100
This Frontier deal was found by Cheapflights users on 8/11. 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.
Fri 11/145:50 amMCO - MDW
Nonstop2h 54mFrontier
Mon 11/178:39 amMDW - MCO
Nonstop2h 41mFrontier
Deal found 8/11$103
This Cheapflightsfares deal was found by Cheapflights users on 8/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/127:00 amMCO - MDW
Nonstop2h 53mFrontier
Sun 9/1410:13 amMDW - MCO
Nonstop2h 42mFrontier
Deal found 8/12$106
This Frontier deal was found by Cheapflights users on 8/11. 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.
Thu 10/97:50 amMCO - MDW
Nonstop2h 57mFrontier
Mon 10/135:28 pmMDW - MCO
Nonstop2h 42mFrontier
Deal found 8/11$108
This Priceline deal was found by Cheapflights users on 8/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/208:00 amMCO - MDW
Nonstop2h 51mFrontier
Sat 9/2010:51 amMDW - MCO
Nonstop2h 42mFrontier
Deal found 8/11$109
This Frontier deal was found by Cheapflights users on 8/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/197:00 amMCO - MDW
Nonstop2h 53mFrontier
Mon 9/228:19 amMDW - MCO
Nonstop2h 41mFrontier
Deal found 8/10$114
This CheapOair deal was found by Cheapflights users on 8/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/127:00 amMCO - MDW
Nonstop2h 53mFrontier
Mon 9/158:19 amMDW - MCO
Nonstop2h 41mFrontier
Deal found 8/11$118
This Frontier deal was found by Cheapflights users on 8/11. 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.
Fri 9/57:00 amMCO - MDW
Nonstop2h 53mFrontier
Sun 9/710:13 amMDW - MCO
Nonstop2h 42mFrontier
Deal found 8/11$122
This Frontier deal was found by Cheapflights users on 8/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/111:16 pmMCO - MDW
Nonstop2h 55mFrontier
Thu 10/1610:49 amMDW - MCO
Nonstop2h 38mFrontier
Deal found 8/12$123
This Frontier deal was found by Cheapflights users on 8/11. 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.
Mon 9/85:35 amMCO - MDW
Nonstop2h 48mFrontier
Mon 9/158:19 amMDW - MCO
Nonstop2h 41mFrontier
Deal found 8/11$125

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 August 13, 2025.
Use the filters below to find and compare flights from Orlando Airport to Chicago Midway Airport that are best for you.

Fly from

Orlando

Fly to

Midway

Route

Depart

Return

Price

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 9/27

8:00 am-9:51 am

Nonstop2h 51m

Chicago Midway

Mon 9/29

8:19 am-12:00 pm

Nonstop2h 41m

$98

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 9/26

7:00 am-8:53 am

Nonstop2h 53m

Chicago Midway

Mon 9/29

8:19 am-12:00 pm

Nonstop2h 41m

$98

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 11/6

5:50 am-7:44 am

Nonstop2h 54m

Chicago Midway

Sun 11/9

8:39 am-12:20 pm

Nonstop2h 41m

$100

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 9/26

7:00 am-8:53 am

Nonstop2h 53m

Chicago Midway

Sun 9/28

10:13 am-1:55 pm

Nonstop2h 42m

$106

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 9/27

8:00 am-9:51 am

Nonstop2h 51m

Chicago Midway

Sun 9/28

10:13 am-1:55 pm

Nonstop2h 42m

$106

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 9/12

7:00 am-8:53 am

Nonstop2h 53m

Chicago Midway

Mon 9/15

8:19 am-12:00 pm

Nonstop2h 41m

$106

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 9/12

7:00 am-8:53 am

Nonstop2h 53m

Chicago Midway

Sun 9/14

10:13 am-1:55 pm

Nonstop2h 42m

$106

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 9/19

7:00 am-8:53 am

Nonstop2h 53m

Chicago Midway

Mon 9/22

8:19 am-12:00 pm

Nonstop2h 41m

$106

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 9/19

7:00 am-8:53 am

Nonstop2h 53m

Chicago Midway

Sun 9/21

10:13 am-1:55 pm

Nonstop2h 42m

$106

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Mon 10/27

2:26 pm-4:20 pm

Nonstop2h 54m

Chicago Midway

Mon 11/10

8:39 am-12:20 pm

Nonstop2h 41m

$106

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 23 results
1
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The best insider tips for Orlando Airport to Chicago Midway Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Orlando Airport to Chicago Midway Airport trip
Airlines
Frontier

Frontier's UpFront Plus seats guarantee an empty middle seat for extra comfort.


Frontier offers no in-flight entertainment or Wi-Fi; bring a book or pre-load entertainment.

Read more about Frontierby Marisa Garcia
Southwest

Southwest offers two free checked bags, including oversized items like skis or golf clubs.


Enjoy free in-flight entertainment with early-release movies and live TV on Southwest flights.

Read more about Southwestby Marisa Garcia
Airports
MCO

Use MCO Reserve to pre-book a security line spot, ensuring a smoother departure experience without long waits.

Read more about MCOby Paul Rubio
MDW

Take the Orange Line from MDW to reach downtown Chicago in under 30 minutes, offering a convenient and affordable option.

Read more about MDWby Ramsey Qubein
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Frontier and Southwest

Marisa Garcia

Marisa Garcia

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

Ramsey Qubein

Ramsey Qubein

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

Paul Rubio

Paul Rubio

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

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 Airport to Chicago Midway Airport

How far ahead should I book a flight from Orlando Airport 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 August 8, 2025.

Booking 66 days in advance of your planned departure date is, on average, the best time to get cheap flights from Orlando Airport to Chicago Midway Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, April is the cheapest month in which you can book a flight from Orlando Airport to Chicago Midway Airport (average of $160). Flying from Orlando Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 MCO 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 August 13, 2025.

A simple way to save on the total cost of your ticket is to fly from Orlando Airport to Chicago Midway Airport at noon. If you’re flexible enough to do this you can expect to save up to 37% on your trip compared to booking a flight in the evening.

What is the cheapest day to fly from Orlando Airport 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 August 10, 2025.

Travelers seeking maximum savings on their Orlando Airport to Chicago Midway Airport flight should consider departing on Friday at noon when fares are most often at their lowest. Sunday 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 August 13, 2025.
See what other customers who have flown with Southwest, Delta, and Frontier from Orlando Airport to Chicago Midway 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
4,246 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

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
8.0
Very good
7,979 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

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
3,221 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

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.

  • What is the cheapest airline to fly from Orlando Airport to Chicago Midway Airport round-trip?

    Cheapflights users have booked flights from Orlando Airport to Chicago Midway Airport round-trip from $98. Frontier is currently priced 52% below the average price you’ll pay for this route.

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

    Looking at all options, your cheapest flight can be booked for $60. While the most popular route (Orlando - Chicago Midway) can be booked for $62 on average our data indicates $199 when flying from Orlando Airport to Chicago Midway Airport.

  • 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 Airport to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Orlando Airport to Chicago Midway Airport (average of $160). Flying from Orlando Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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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.
Orlando to O'Hare Intl flights
Orlando Sanford Intl to Rockford flights
Orlando to Rockford flights

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 August 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$170FlexibilityNo cancel feeOn-time62%
DeltaCheapest$114Average$216FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$159Average$335FlexibilityNo cancel feeOn-time63%

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