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$79+ 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Orlando to Chicago Midway are usually found in February or September, booked 67 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 June 12, 2025.

Round-trip from

$126
(Cheapflightsfares)

One-way from

$79
(Southwest)

Popular in

March

Cheapest in

February

Average price

$217

Good round-trip deal

$167 or less

Good one-way deal

$81 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. 3% potential increase in price ($8 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 June 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 June 12, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/308:00 amMCO - MDW
Nonstop2h 54mFrontier
Fri 9/58:34 amMDW - MCO
Nonstop2h 41mFrontier
Deal found 6/11$126
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/157:35 amMCO - MDW
Nonstop2h 45mSouthwest
Tue 8/197:55 pmMDW - MCO
Nonstop2h 35mSouthwest
Deal found 6/11$158
This Mytrip deal was found by Cheapflights users on 6/10. 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.
Fri 7/258:27 amMCO - MDW
1 stop6h 37mAllegiant Air
Fri 8/11:11 pmMDW - MCO
1 stop24h 08mAllegiant Air
Deal found 6/10$206
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/196:15 amMCO - MDW
1 stop7h 14mDelta
Tue 7/229:25 amMDW - MCO
1 stop6h 21mDelta
Deal found 6/10$257
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/215:30 amMCO - MDW
2 stops28h 12mMultiple Airlines
Sun 8/2411:03 amMDW - MCO
2 stops28h 04mMultiple Airlines
Deal found 6/11$296

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 June 12, 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 8/30

8:00 am-9:54 am

Nonstop2h 54m

Chicago Midway

Fri 9/5

8:34 am-12:15 pm

Nonstop2h 41m

$126

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 8/15

7:35 am-9:20 am

Nonstop2h 45m

Chicago Midway

Tue 8/19

7:55 pm-11:30 pm

Nonstop2h 35m

$158

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 7/25

8:27 am-2:04 pm

1 stop6h 37m

Chicago Midway

Fri 8/1

1:11 pm-2:19 pm

1 stop24h 08m

$206

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 7/19

6:15 am-12:29 pm

1 stop7h 14m

Chicago Midway

Tue 7/22

9:25 am-4:46 pm

1 stop6h 21m

$257

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 7/25

8:27 am-2:04 pm

1 stop6h 37m

Chicago Midway

Fri 8/1

2:46 pm-10:57 pm

2 stops31h 11m

$281

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 8/13

10:05 am-11:50 am

Nonstop2h 45m

$79

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 9/3

1:49 pm-12:06 pm

1 stop23h 17m

$85

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Mon 8/18

8:30 am-2:04 pm

1 stop6h 34m

$98

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 9/9

2:00 pm-6:37 pm

1 stop5h 37m

$109

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sun 7/27

6:50 am-9:41 am

2 stops27h 51m

$133

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 June 9, 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 June 12, 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 40% 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 June 8, 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.

Weekly flight availability from Orlando Airport to Chicago Midway Airport

Explore weekly flight availability from Orlando to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 12, 2025.

The most flights from MCO to MDW are scheduled on a Tuesday (13 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
Read through reviews of airlines operating flights from Orlando to Chicago, such as Southwest, Delta and Allegiant Air. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

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
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

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.
Allegiant Air
7.3
Good
725 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

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
6.0
Okay
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

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

    Cheapflights users have booked flights from Orlando Airport to Chicago Midway Airport round-trip from $126. Other airlines that can offer you cheap pricing are Southwest, from $158, and Allegiant Air, from $206. Frontier is currently priced 37% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Orlando Airport to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $79 on Southwest. Other airlines that offer cheap prices include Frontier from $85 and Allegiant Air from $98 one-way.

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

    Looking at all options, your cheapest flight can be booked for $48. While the most popular route (Orlando - Chicago Midway) can be booked for $127 on average our data indicates $171 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 Orlando Airport?

Book flights to Orlando Airport if you plan to visit one of these locations
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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$77Average$166FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$181Average$369FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$286FlexibilityNo cancel feeOn-timeN/A

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