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$57+ 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 8/21. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — MDW
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
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 64 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 July 1, 2025.

Round-trip from

$103
(Priceline)

One-way from

$57
(Priceline)

Popular in

March

Cheapest in

January

Average price

$248

Good round-trip deal

$162 or less

Good one-way deal

$99 or less
From Orlando (ORL) to Chicago Midway
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One-way flight from Orlando (ORL) to Chicago Midway
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Highest demand for flights based on searches. 2% potential increase in price ($7 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Orlando (ORL) to Chicago Midway.
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Price to beat on a one-way flight from Orlando (ORL) 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 July 1, 2025.

This Priceline deal was found by Cheapflights users on 6/30. 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.
Sun 9/147:00 amMCO - MDW
Nonstop2h 53mFrontier
Thu 9/181:59 pmMDW - MCO
1 stop9h 00mFrontier
Deal found 6/30$103
This Southwest deal was found by Cheapflights users on 6/30. 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 8/294:25 pmMCO - MDW
Nonstop2h 50mSouthwest
Wed 9/38:05 pmMDW - MCO
Nonstop2h 35mSouthwest
Deal found 6/30$158

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 July 1, 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

Sun 9/14

7:00 am-8:53 am

Nonstop2h 53m

Chicago Midway

Thu 9/18

1:59 pm-11:59 pm

1 stop9h 00m

$103

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 8/29

4:25 pm-6:15 pm

Nonstop2h 50m

Chicago Midway

Wed 9/3

8:05 pm-11:40 pm

Nonstop2h 35m

$158

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 8/21

12:12 pm-5:05 pm

1 stop5h 53m

$57

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 9/16

11:45 am-1:25 pm

Nonstop2h 40m

$79

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 8/7

8:00 am-11:48 am

1 stop4h 48m

$99

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Mon 7/21

8:27 am-2:04 pm

1 stop6h 37m

$101

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

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 June 27, 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 64 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, April is the cheapest month in which you can book a flight from Orlando to Chicago Midway Airport (average of $160). Flying from Orlando 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 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 July 1, 2025.

It’s typically best to fly out from Orlando to Chicago Midway Airport at noon. Doing so could potentially save you 42% on the flight price compared to flying in the evening, 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 June 29, 2025.

Travelers seeking maximum savings on their Orlando 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 July 1, 2025.
Read through reviews of airlines operating flights from Orlando to Chicago Midway Airport, 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
4,273 reviews

Entertainment

7.6

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.2

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
4,273 reviews
Southwest
8.0
Very good
4,273 reviews

Entertainment

7.6

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.2

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
7,973 reviews
Southwest
8.0
Very good
4,273 reviews

Entertainment

7.6

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.2

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
7.2
Good
710 reviews
Southwest
8.0
Very good
4,273 reviews

Entertainment

7.6

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.2

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
5.9
Fair
3,291 reviews
Southwest
8.0
Very good
4,273 reviews

Entertainment

7.6

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.2

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 to Chicago Midway Airport round-trip?

    Cheapflights users have booked flights from Orlando to Chicago Midway Airport round-trip from $103. Another airline that can offer you cheap pricing is Southwest. Users have found that Frontier is 55% cheaper than the other options available to this destination.

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

    One-way options have recently been found by users for as low as $57 on Frontier. Other airlines that offer cheap prices include Southwest from $79 and Delta from $99 one-way.

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

    While on average a flight from Orlando to Chicago Midway Airport is generally $185, our data shows the cheapest flight currently is $72. When looking at the most popular route, (Orlando - Chicago Midway), you can expect to pay $100 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, April is the cheapest month in which you can book a flight from Orlando to Chicago Midway Airport (average of $160). Flying from Orlando 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?

Book flights to Orlando if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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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 July 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$77Average$166FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$173Average$364FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$286FlexibilityNo cancel feeOn-timeN/A

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