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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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ORL
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Find cheap flights from Midway to Orlando with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

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Cheapflights Tip: The best prices from Chicago Midway to Orlando are usually found in August or February, booked 52 days in advance, depart on a Thursday or Friday and return on a Friday

Cheap 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 December 15, 2025.

This Frontier deal was found by Cheapflights users on 12/13. 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.
Wed 12/313:10 pmMDW - MCO
Nonstop2h 48mFrontier
Thu 1/85:20 amMCO - MDW
1 stop7h 11mFrontier
Deal found 12/13$108
This Frontier deal was found by Cheapflights users on 12/13. 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.
Wed 12/313:10 pmMDW - MCO
Nonstop2h 48mFrontier
Sun 1/119:03 pmMCO - MDW
Nonstop2h 56mFrontier
Deal found 12/13$135
This Kiwi.com deal was found by Cheapflights users on 12/12. 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.
Wed 12/313:10 pmMDW - MCO
Nonstop2h 48mMultiple Airlines
Wed 1/75:15 pmMCO - MDW
1 stop6h 02mMultiple Airlines
Deal found 12/12$154
This Kiwi.com deal was found by Cheapflights users on 12/14. 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.
Wed 12/248:15 amMDW - MCO
1 stop15h 10mFrontier
Fri 1/99:13 pmMCO - MDW
Nonstop2h 56mFrontier
Deal found 12/14$160
This Kiwi.com deal was found by Cheapflights users on 12/14. 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.
Wed 12/248:15 amMDW - MCO
1 stop15h 10mFrontier
Thu 1/85:20 amMCO - MDW
1 stop7h 11mFrontier
Deal found 12/14$171
This Kiwi.com deal was found by Cheapflights users on 12/12. 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.
Wed 12/313:10 pmMDW - MCO
Nonstop2h 48mFrontier
Wed 1/75:20 amMCO - MDW
2 stops9h 46mFrontier
Deal found 12/12$190
This Expedia deal was found by Cheapflights users on 12/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:10 pmMDW - MCO
Nonstop2h 48mFrontier
Mon 1/512:15 pmMCO - MDW
1 stop10h 57mFrontier
Deal found 12/13$191
This Frontier deal was found by Cheapflights users on 12/13. 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 12/153:10 pmMDW - MCO
Nonstop2h 48mFrontier
Thu 12/257:58 pmMCO - MDW
Nonstop3h 00mFrontier
Deal found 12/13$194
This Frontier deal was found by Cheapflights users on 12/13. 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.
Tue 12/306:14 amMDW - MCO
1 stop9h 22mFrontier
Fri 1/99:13 pmMCO - MDW
Nonstop2h 56mFrontier
Deal found 12/13$195
This Southwest deal was found by Cheapflights users on 12/12. 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.
Wed 12/311:25 pmMDW - MCO
1 stop4h 25mSouthwest
Wed 1/710:45 amMCO - MDW
1 stop4h 45mSouthwest
Deal found 12/12$198

Find 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 December 15, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$94
(CheapOair)

One-way from

$50
(CheapOair)

Popular in

December

Cheapest in

August

Average price

$388

Good round-trip deal

$177 or less

Good one-way deal

$95 or less
Provider with most accurate pricing for Chicago Midway-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Orlando (ORL) flights.
Search Deals
From Chicago Midway to Orlando (ORL)
Search Deals
One-way flight from Chicago Midway to Orlando (ORL)
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Orlando (ORL).
Search Deals
Price to beat on a one-way flight from Chicago Midway to Orlando (ORL).
Search Deals

Cheapflights Fare Finder

 
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 December 15, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Orlando that are best for you.

Fly from

Midway

Fly to

Orlando

Route

Depart

Return

Price

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 1/18

5:00 am-8:45 am

Nonstop2h 45m

Orlando

Wed 1/21

2:35 pm-4:30 pm

Nonstop2h 55m

$167

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 2/7

2:45 pm-6:20 pm

Nonstop2h 35m

Orlando

Wed 2/11

7:25 am-9:20 am

Nonstop2h 55m

$177

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 1/12

5:30 pm-9:05 pm

Nonstop2h 35m

Orlando

Tue 1/13

2:35 pm-4:30 pm

Nonstop2h 55m

$178

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 1/27

2:20 pm-8:45 pm

1 stop5h 25m

Orlando

Tue 2/10

7:05 pm-9:00 pm

Nonstop2h 55m

$183

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 2/3

5:00 am-8:45 am

Nonstop2h 45m

Orlando

Tue 2/10

10:45 am-2:30 pm

1 stop4h 45m

$183

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 1/31

5:40 pm-9:15 pm

Nonstop2h 35m

Orlando

Sat 2/7

6:00 pm-7:55 pm

Nonstop2h 55m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 2/23

8:15 am-11:55 am

Nonstop2h 40m

Orlando

Fri 2/27

6:50 am-8:45 am

Nonstop2h 55m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 1/24

5:40 pm-9:15 pm

Nonstop2h 35m

Orlando

Fri 1/30

7:25 am-9:20 am

Nonstop2h 55m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 1/17

5:40 pm-9:15 pm

Nonstop2h 35m

Orlando

Tue 1/20

8:15 am-12:25 pm

1 stop5h 10m

$202

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 1/10

9:45 am-2:50 pm

1 stop4h 05m

Orlando

Sat 1/17

7:00 am-8:55 am

Nonstop2h 55m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

Showing 1-10 of 32 results
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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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
JustAirTicketPrice Accuracy-Trust 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 Chicago Midway Airport-Orlando flights, users find the pricing of Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on Chicago Midway Airport-Orlando flight deals on Cheapflights vs. Mytrip >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 Mytrip the most. Mytrip 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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Orlando

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 December 12, 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 52 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Orlando (average of $59). Flying from Chicago Midway Airport to Orlando in June is currently the most expensive (average of $178). 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 December 15, 2025.

It’s typically best to fly out from Chicago Midway Airport to Orlando in the afternoon. Doing so could potentially save you 16% on the flight price compared to flying in the evening, 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 December 13, 2025.

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

How often are flights from Chicago to Orlando delayed?

About 13% of weekly flights between Chicago and Orlando have experienced delays in the past year, with the average delay time being 136 minutes.

What is the most punctual flight time for Chicago to Orlando flights?

Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Orlando flights?

Over the last year, Frontier have had the lowest number of delays on this route, with just 11% of flights being delayed.

The best insider tips for Chicago Midway Airport to Orlando flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Orlando trip
Airlines
Southwest

Southwest offers free snacks and non-alcoholic beverages, enhancing your in-flight experience.


Southwest's Rapid Rewards program offers points for every dollar spent, with no blackout dates.

Read more about SouthwestBy Marisa Garcia
Frontier

Frontier's UpFront Plus seats guarantee an empty middle seat for added comfort.


Frontier offers extra comfort seats for a fee, ideal for flights around 3 hours.

Read more about FrontierBy Marisa Garcia
Airports
MDW

Use the 'L' train to reach MDW easily. The Orange Line stops directly at the airport, offering a quick 30-minute ride to the city center.

Read more about MDWBy Ramsey Qubein
MCO

Skip renting a car at MCO; rideshares are affordable and convenient for exploring Orlando and reaching Disney resorts.

Read more about MCOBy Paul Rubio
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Southwest and Frontier

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Paul Rubio

Paul Rubio

Expert on MCO

Paul Rubio

Paul Rubio

Travel journalist and photographer Paul Rubio is a Miami native (and current resident), who has lived in nine countries and traveled to 137. He is an expert in luxury travel, eco-travel, loyalty programs, hotels, airports and airlines. He is a contributing editor at AFAR, Condé Nast Traveler, LUXURY Magazine, and Palm Beach Illustrated.

Read more

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 December 15, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Spirit Airlines from Chicago Midway Airport to Orlando. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,249 reviews

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

7.9

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
7.9
Good
4,249 reviews
Southwest
7.9
Good
4,249 reviews

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

7.9

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
7.9
Good
8,008 reviews
Southwest
7.9
Good
4,249 reviews

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

7.9

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.
Spirit Airlines
6.3
Okay
8,188 reviews
Southwest
7.9
Good
4,249 reviews

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

7.9

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
5.8
Fair
3,079 reviews
Southwest
7.9
Good
4,249 reviews

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

7.9

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.

  • How long is the flight from Chicago Midway Airport to Orlando?

    There are many flights that can get you from Chicago Midway Airport to Orlando in 2h 45m. Fly via Southwest to get the fastest option. The distance between Chicago Midway Airport and Orlando is about 990 mi. Generally, flights for this route are nonstop.

  • What are the cheapest airlines flying from Chicago Midway Airport to Orlando round-trip?

    Currently priced at $35, Spirit Airlines will fly you from Chicago Midway Airport to Orlando and back. In addition to Spirit Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Frontier and Delta - these airlines can fly you to your destination from $81 and $98, respectively. Spirit Airlines is priced at 86% lower than the current average price of a flight leaving 3 months from now.

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

    Looking at all options, your cheapest flight can be booked for $33. While the most popular route (Chicago Midway - Orlando) can be booked for $58 on average, our data indicates $208 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Orlando (average of $59). Flying from Chicago Midway Airport to Orlando in June is currently the most expensive (average of $178). 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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Alternative routes for Midway to Orlando

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Midway to Orlando

Discover the top 4 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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$63Average$193FlexibilityNo cancel feeOn-time65%
FrontierCheapest$82Average$197FlexibilityNo cancel feeOn-time62%
DeltaCheapest$196Average$533FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$198Average$395FlexibilityNo cancel feeOn-time63%

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