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$53+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — MDW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from Orlando to Chicago Midway are usually found in February or September, booked 66 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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$80
(Cheapflightsfares)

One-way from

$53
(Trip.com)

Popular in

December

Cheapest in

February

Average price

$126

Good round-trip deal

$142 or less

Good one-way deal

$111 or less
Provider with most accurate pricing for Orlando (ORL)-Chicago Midway flight deals.
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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
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Highest demand for flights based on searches. 8% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/251:13 pmMCO - MDW
Nonstop2h 59mFrontier
Tue 3/48:30 amMDW - MCO
Nonstop2h 48mFrontier
Deal found 2/18$80
This Kissandfly.com deal was found by Cheapflights users on 2/19. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/279:05 amMCO - MDW
2 stops13h 24mMultiple Airlines
Mon 3/312:43 pmMDW - MCO
Nonstop2h 48mMultiple Airlines
Deal found 2/19$195
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/254:10 pmMCO - MDW
1 stop7h 13mDelta
Wed 3/2612:51 pmMDW - MCO
1 stop5h 52mDelta
Deal found 2/20$209
This Southwest deal was found by Cheapflights users on 2/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/88:50 pmMCO - MDW
Nonstop2h 50mSouthwest
Wed 5/217:55 pmMDW - MCO
Nonstop2h 35mSouthwest
Deal found 2/18$264

Find flights from Orlando to Midway within your budget

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 February 20, 2025.

Fly from

Orlando

Fly to

Midway

Route

Depart

Return

Price

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 3/4

1:13 pm-3:12 pm

Nonstop2h 59m

Chicago Midway

Sat 3/8

9:48 am-1:33 pm

Nonstop2h 45m

$90

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 3/25

4:10 pm-10:23 pm

1 stop7h 13m

Chicago Midway

Wed 3/26

12:51 pm-7:43 pm

1 stop5h 52m

$209

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 3/6

7:00 am-10:06 pm

2 stops16h 06m

Chicago Midway

Mon 3/10

12:49 pm-4:37 pm

Nonstop2h 48m

$227

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 5/8

8:50 pm-10:40 pm

Nonstop2h 50m

Chicago Midway

Wed 5/21

7:55 pm-11:30 pm

Nonstop2h 35m

$264

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 5/28

3:30 pm-11:55 pm

1 stop9h 25m

$53

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 3/25

7:15 am-9:15 am

Nonstop3h 00m

$95

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 4/22

5:30 am-9:07 am

1 stop4h 37m

$109

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sun 5/4

8:30 am-10:09 am

2 stops26h 39m

$166

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*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.

Travel insights for flights from Orlando to Midway

Get recent, data-driven insights about flights from Orlando to Midway including ideal travel times, pricing trends, and more.

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 February 14, 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 66 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 February 20, 2025.

It’s typically best to fly out from Orlando to Chicago Midway Airport at noon. Doing so could potentially save you 8% 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 February 16, 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.

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 February 20, 2025.
Read through reviews of airlines operating flights from Orlando to Chicago, such as Southwest, Delta and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

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
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

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
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

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
6.0
Okay
3,355 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

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 $80. Other airlines that can offer you cheap pricing are Delta, from $209, and Southwest, from $243. Users have found that Frontier is 56% 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 $53 on Frontier. Other airlines that offer cheap prices include Southwest from $95 and Delta from $109 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 $191, our data shows the cheapest flight currently is $44. When looking at the most popular route, (Orlando - Chicago Midway), you can expect to pay $80 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
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Valparaiso
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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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$74Average$147FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$179Average$390FlexibilityNo cancel feeOn-time63%
DeltaCheapest$227Average$334FlexibilityNo cancel feeOn-timeN/A
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