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$56+ 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 12/18. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — MDW
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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The best prices from Orlando to Chicago Midway are usually found in April or February, booked 68 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 20, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

July

Cheapest in

April

Round-trip from

$108
(Frontier)

One-way from

$56
(Trip.com)
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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High demand for flights, 17% potential price rise
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Best time to find cheap flights, 22% potential price drop
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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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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 20, 2024.

This Frontier deal was found by Cheapflights users on 11/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/168:26 amMCO - MDW
Nonstop2h 55mFrontier
Mon 12/1612:36 pmMDW - MCO
1 stop10h 22mFrontier
Deal found 11/19$113
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/176:15 amMCO - MDW
1 stop4h 35mDelta
Tue 12/1712:44 pmMDW - MCO
1 stop6h 07mDelta
Deal found 11/19$212
This Southwest deal was found by Cheapflights users on 11/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/76:25 amMCO - MDW
Nonstop2h 55mSouthwest
Tue 12/107:15 pmMDW - MCO
Nonstop2h 40mSouthwest
Deal found 11/19$281

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 1/9

12:40 pm-6:37 pm

1 stop6h 57m

Chicago Midway

Mon 1/13

4:28 pm-1:48 am

1 stop8h 20m

$108

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 12/17

6:15 am-9:50 am

1 stop4h 35m

Chicago Midway

Tue 12/17

12:44 pm-7:51 pm

1 stop6h 07m

$212

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 12/14

8:25 am-10:15 am

Nonstop2h 50m

Chicago Midway

Sun 12/15

8:00 pm-11:40 pm

Nonstop2h 40m

$258

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 12/18

10:52 pm-6:39 am

1 stop8h 47m

$56

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 1/15

1:05 pm-3:00 pm

Nonstop2h 55m

$79

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 1/8

8:45 am-1:08 pm

1 stop5h 23m

$98

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 11/28

7:02 am-3:01 pm

1 stop8h 59m

$102

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 2/8

8:15 am-8:31 am

2 stops25h 16m

$168

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Mon 3/17

6:20 pm-5:46 pm

2 stops24h 26m

$240

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 1/14

3:30 pm-12:10 pm

2 stops21h 40m

$243

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy2 starsTrust Score*3 stars
Trip.comPrice Accuracy2 starsTrust Score*3 stars
Kiwi.comPrice 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 November 15, 2024.

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 68 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, December is the cheapest month in which you can book a flight from Orlando to Chicago Midway Airport (average of $159). Flying from Orlando to Chicago Midway Airport in July is currently the most expensive (average of $231). 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 20, 2024.

It’s typically best to fly out from Orlando to Chicago Midway Airport at noon. Doing so could potentially save you 20% 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 November 18, 2024.

Travelers seeking maximum savings on their Orlando to Chicago Midway Airport flight should consider departing on Thursday afternoons 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.

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 November 20, 2024.
Read through reviews of airlines operating flights from Orlando to Chicago, such as Frontier and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Porter Airlines
7.8
Good
288 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

WestJet
7.3
Good
2,811 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Frontier
6.1
Okay
3,539 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

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 $108. Another airline that can offer you cheap pricing is Delta. Users have found that Frontier is 38% 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 $56 on Frontier. Other airlines that offer cheap prices include Southwest from $79 and Delta from $98 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 $187, our data shows the cheapest flight currently is $55. When looking at the most popular route, (Orlando - Chicago Midway), you can expect to pay $112 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, December is the cheapest month in which you can book a flight from Orlando to Chicago Midway Airport (average of $159). Flying from Orlando to Chicago Midway Airport in July is currently the most expensive (average of $231). 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.

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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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$74Average$154FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$178Average$324FlexibilityNo cancel feeOn-time63%
DeltaCheapest$227Average$317FlexibilityNo cancel feeOn-timeN/A
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