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$50+ Cheap flights from Midway (MDW) to Orlando (ORL)

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 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ORL
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
1 adult, Economy
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The best prices from Chicago Midway to Orlando are usually found in May or April, booked 81 days in advance, depart on a Thursday or Saturday and return on a Friday

Cheap flight deals from Midway to Orlando

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Orlando (ORL). 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 febrero 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$118
(Kiwi.com)

One-way from

$50
(Trip.com)

Popular in

June

Cheapest in

May

Average price

$261

Good round-trip deal

$178 or less

Good one-way deal

$75 or less
Provider with most accurate pricing for Chicago Midway-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Orlando (ORL) flights.
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From Chicago Midway to Orlando (ORL)
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One-way flight from Chicago Midway to Orlando (ORL)
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Highest demand for flights based on searches. 21% potential increase in price ($81 potential increase over avg. RT price).
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Cheapest flight prices on average. 14% potential price decrease ($38 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 Chicago Midway to Orlando (ORL).
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Price to beat on a one-way flight from Chicago Midway to Orlando (ORL).
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Find flight deals from Midway to Orlando

Cheapest flights from Midway to Orlando
Explore the most affordable flight options available from Midway to Orlando. Find the lowest fares from popular airlines and budget airlines, with prices last updated on febrero 20, 2025.

This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/14:40 pmMDW - MCO
Nonstop2h 50mFrontier
vie. 4/45:54 pmMCO - MDW
Nonstop3h 01mFrontier
Deal found 2/19$118
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/27:00 pmMDW - SFB
1 stop14h 35mAllegiant Air
jue. 6/59:53 pmSFB - MDW
1 stop22h 53mAllegiant Air
Deal found 2/19$213
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/187:05 amMDW - MCO
1 stop4h 15mSouthwest
mar. 3/256:30 pmMCO - MDW
1 stop5h 15mSouthwest
Deal found 2/20$233
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 3/302:55 pmMDW - MCO
1 stop7h 25mDelta
mar. 4/85:30 amMCO - MDW
1 stop4h 37mDelta
Deal found 2/19$249

Find flights from Midway to Orlando within your budget

Customize your flight search to find flights from Midway to Orlando 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 febrero 20, 2025.

Fly from

Midway

Fly to

Orlando

Route

Depart

Return

Price

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

mar. 4/1

4:40 pm-8:30 pm

Nonstop2h 50m

Orlando

vie. 4/4

5:54 pm-7:55 pm

Nonstop3h 01m

$118

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

mar. 3/18

7:05 am-12:20 pm

1 stop4h 15m

Orlando

mar. 3/25

6:30 pm-10:45 pm

1 stop5h 15m

$233

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

jue. 6/12

8:50 am-9:10 pm

1 stop11h 20m

Orlando

lun. 6/16

8:24 am-2:03 pm

1 stop6h 39m

$238

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

dom. 3/30

2:55 pm-11:20 pm

1 stop7h 25m

Orlando

mar. 4/8

5:30 am-9:07 am

1 stop4h 37m

$249

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

jue. 3/6

2:22 pm-7:56 am

2 stops16h 34m

Orlando Sanford Intl

lun. 3/10

8:51 pm-5:46 pm

2 stops21h 55m

$384

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

mié. 4/2

2:23 pm-11:22 pm

1 stop7h 59m

$50

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

mar. 5/13

7:55 pm-11:30 pm

Nonstop2h 35m

$95

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

mar. 3/25

4:59 pm-11:55 pm

1 stop5h 56m

$105

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

dom. 4/13

2:19 pm-8:29 am

3 stops41h 10m

$152

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

jue. 5/15

11:43 am-7:33 pm

2 stops30h 50m

$163

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 11 results
1
2

Compare providers for flights from Midway to Orlando

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 Midway to Orlando in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy1 starTrust Score*2 stars
Kiwi.comPrice Accuracy3 starsTrust Score*2 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
GotogatePrice 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 Chicago Midway Airport-Orlando flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Orlando flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Orlando flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Orlando 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 Chicago Midway Airport-Orlando 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 Midway to Orlando

Have a flexible travel schedule? Discover the best time to fly to Orlando from Midway 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 Midway to Orlando

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

How far ahead should I book a flight from Chicago Midway Airport to Orlando?

Use this chart to determine the optimal time to book a round-trip flight from Midway to Orlando. Price data was last updated on February 14, 2025.

To ensure you get the cheapest price possible for a flight from Chicago Midway Airport to Orlando, you should look to book at least 81 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago Midway Airport to Orlando?

Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Orlando (average of $206). Flying from Chicago Midway Airport to Orlando in November is currently the most expensive (average of $289). 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 MDW to ORL?

Find hourly flight availability from Midway to Orlando. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated febrero 20, 2025.

It’s typically best to fly out from Chicago Midway Airport to Orlando in the evening. Doing so could potentially save you 7% on the flight price compared to flying at noon, which is usually more expensive.

What is the cheapest day to fly from Chicago Midway Airport to Orlando?

Use this chart to determine the cheapest time to fly round-trip from Midway to Orlando. Price data was last updated on February 16, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Orlando flight should consider departing on Friday afternoons when fares are most often at their lowest. Wednesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Orlando by month

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

In terms of precipitation, rainfall in Orlando ranges from 2.4 - 8.7 inches per month. June is typically the wettest month, when rainfall can reach 8.7 in. November is typically the driest time to visit Orlando when rainfall is around 2.4 in.

Temperature in Orlando by month

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

If weather is an important factor for your trip to Orlando, 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 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 60.8 F).

Reviews of airlines servicing Orlando

Get insights into the airlines that provide service to Orlando. 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 Orlando. Reviews last updated febrero 20, 2025.
To help decide which airline to fly from Chicago to Orlando, see what other customers have to say about Southwest, Delta and Allegiant Air. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

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

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Allegiant Air
7.3
Good
765 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

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

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from Midway to Orlando. 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 Chicago Midway Airport to Orlando round-trip?

    Currently priced at $118, Frontier will fly you from Chicago Midway Airport to Orlando and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Southwest and Delta - these airlines can fly you to your destination from $199 and $249, respectively. Frontier is priced at 60% lower than the current average price of a flight leaving 3 months from now.

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

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $50. However, be on the lookout for offers from Southwest and Delta, as they are both options that can get you from Chicago Midway Airport to Orlando for a low price.

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

    Looking at all options, your cheapest flight can be booked for $37. While the most popular route (Chicago Midway - Orlando) can be booked for $59 on average our data indicates $225 when flying from Chicago Midway Airport to Orlando.

  • Can I find deals for flights from Midway to Orlando that include hotel bookings?

    Yes. In addition to deals on Midway to Orlando flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Orlando?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Orlando.

  • Can I find deals for business class flights from Midway to Orlando?

    Yes. Cheapflights offers flight deals from Midway to Orlando 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 Chicago Midway Airport to Orlando?

    Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Orlando (average of $206). Flying from Chicago Midway Airport to Orlando in November is currently the most expensive (average of $289). 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

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Top 5 airlines flying from Midway to Orlando

Discover the top 5 airlines that operate flights from Midway to Orlando. 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 febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$80Average$191FlexibilityNo cancel feeOn-time65%
FrontierCheapest$80Average$215FlexibilityNo cancel feeOn-time62%
DeltaCheapest$196Average$338FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$248Average$411FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$248Average$389FlexibilityNo cancel feeOn-time69%
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