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$58+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
leden 28 — únor 41
út 1/28
út 2/4
1 adult, Economy
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The best prices from Orlando to Chicago Midway are usually found in February or April, 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 (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 leden 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$99
(Frontier)

One-way from

$58
(Trip.com)

Popular in

December

Cheapest in

February

Average price

$179

Good round-trip deal

$165 or less

Good one-way deal

$125 or less
Provider with most accurate pricing for Orlando-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Orlando-Chicago Midway flights.
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From Orlando to Chicago Midway
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One-way flight from Orlando to Chicago Midway
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in January 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 leden 23, 2025.

This Frontier deal was found by Cheapflights users on 1/23. 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.
čt 2/610:39 amMCO - MDW
1 stop8h 47mFrontier
ne 2/910:58 amMDW - MCO
Nonstop2h 47mFrontier
Deal found 1/23$99
This Delta deal was found by Cheapflights users on 1/22. 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.
so 2/156:15 amMCO - MDW
1 stop4h 57mDelta
út 2/185:05 pmMDW - MCO
1 stop4h 33mDelta
Deal found 1/22$214

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 leden 23, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

čt 2/6

10:39 am-6:26 pm

1 stop8h 47m

Chicago Midway

ne 2/9

10:58 am-2:45 pm

Nonstop2h 47m

$99

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

so 2/15

6:15 am-10:12 am

1 stop4h 57m

Chicago Midway

út 2/18

5:05 pm-10:38 pm

1 stop4h 33m

$214

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

út 3/18

7:35 pm-9:30 pm

Nonstop2h 55m

Chicago Midway

st 3/19

7:05 am-12:20 pm

1 stop4h 15m

$277

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

čt 2/27

5:26 pm-7:29 pm

Nonstop3h 03m

$58

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

út 3/11

5:55 pm-7:50 pm

Nonstop2h 55m

$99

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

út 3/18

6:05 am-12:36 pm

1 stop7h 31m

$109

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

čt 5/29

7:00 am-6:41 pm

1 stop12h 41m

$116

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

po 6/2

1:40 pm-7:14 pm

1 stop6h 34m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/23

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 starsTrust Score*3 stars
Trip.comPrice Accuracy2 starsTrust Score*3 stars
CheapOairPrice Accuracy2 starsTrust Score*2 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 star

*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 Airport-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 Airport-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Orlando Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Orlando Airport-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 Airport-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 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 January 17, 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 leden 23, 2025.

A simple way to save on the total cost of your ticket is to fly from Orlando Airport to Chicago Midway Airport in the evening. If you’re flexible enough to do this you can expect to save up to 5% on your trip compared to booking a flight in the afternoon.

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 January 21, 2025.

Travelers seeking maximum savings on their Orlando Airport to Chicago Midway Airport flight should consider departing on Tuesday evenings 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 leden 23, 2025.
Read through reviews of airlines operating flights from Orlando to Chicago, such as Delta, Southwest and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,654 reviews

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.1
Very good
4,654 reviews
Southwest
8.1
Very good
4,654 reviews

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Delta
8.0
Very good
8,512 reviews
Southwest
8.1
Very good
4,654 reviews

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Frontier
6.1
Okay
3,441 reviews
Southwest
8.1
Very good
4,654 reviews

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Boarding

8.2

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 Airport to Chicago Midway Airport round-trip?

    Cheapflights users have booked flights from Orlando Airport to Chicago Midway Airport round-trip from $99. Other airlines that can offer you cheap pricing are Delta, from $214, and Southwest, from $277. Frontier is currently priced 45% 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 $58 on Frontier. Other airlines that offer cheap prices include Southwest from $99 and Delta from $109 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 $63. While the most popular route (Orlando - Chicago Midway) can be booked for $117 on average our data indicates $225 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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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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 leden 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$76Average$165FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$178Average$381FlexibilityNo cancel feeOn-time63%
DeltaCheapest$227Average$307FlexibilityNo cancel feeOn-timeN/A
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