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$70+ 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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ORL
Jun 12 — Jun 191
Fri 6/12
Fri 6/19
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Orlando are usually found in September or August, booked 90 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 May 13, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Tue 6/212:27 pm
MDW
-
MCO
1 stop8h 20m
Frontier
Tue 6/97:53 am
MCO
-
MDW
1 stop15h 18m
Frontier
Deal found 5/12$163
This Kiwi.com deal was found by Cheapflights users on 5/10. 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.
Fri 5/293:42 pm
MDW
-
MCO
1 stop17h 22m
Multiple Airlines
Wed 6/107:53 am
MCO
-
MDW
1 stop15h 18m
Multiple Airlines
Deal found 5/10$164
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Mon 10/266:40 am
MDW
-
MCO
1 stop6h 57m
Frontier
Sat 10/315:29 pm
MCO
-
MDW
1 stop5h 24m
Frontier
Deal found 5/12$167
This Southwest deal was found by Cheapflights users on 5/12. 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.
Tue 9/153:30 pm
MDW
-
MCO
Nonstop2h 35m
Southwest
Tue 9/225:25 pm
MCO
-
MDW
Nonstop2h 50m
Southwest
Deal found 5/12$169
This Kiwi.com deal was found by Cheapflights users on 5/11. 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.
Tue 6/212:27 pm
MDW
-
MCO
1 stop6h 05m
Multiple Airlines
Mon 6/811:03 am
MCO
-
MDW
1 stop4h 45m
Multiple Airlines
Deal found 5/11$173
This Southwest deal was found by Cheapflights users on 5/12. 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.
Tue 6/168:10 pm
MDW
-
MCO
Nonstop2h 35m
Southwest
Tue 6/234:40 pm
MCO
-
MDW
1 stop4h 10m
Southwest
Deal found 5/12$175
This Southwest deal was found by Cheapflights users on 5/12. 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.
Tue 6/95:20 pm
MDW
-
MCO
1 stop5h 20m
Southwest
Tue 6/161:30 pm
MCO
-
MDW
Nonstop2h 45m
Southwest
Deal found 5/12$179
This Southwest deal was found by Cheapflights users on 5/10. 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.
Tue 7/149:10 am
MDW
-
MCO
1 stop5h 05m
Southwest
Wed 7/224:40 pm
MCO
-
MDW
1 stop4h 10m
Southwest
Deal found 5/10$180
This Kiwi.com deal was found by Cheapflights users on 5/11. 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 5/2712:04 pm
MDW
-
MCO
1 stop6h 28m
Frontier
Tue 6/167:53 am
MCO
-
MDW
1 stop15h 18m
Frontier
Deal found 5/11$181
This Kiwi.com deal was found by Cheapflights users on 5/10. 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.
Tue 6/96:00 am
MDW
-
MCO
1 stop15h 09m
Frontier
Tue 6/165:25 am
MCO
-
MDW
1 stop6h 47m
Frontier
Deal found 5/10$182
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Mon 6/158:20 pm
MDW
-
SFB
1 stop14h 32m
Allegiant Air
Sun 6/288:58 pm
SFB
-
MDW
1 stop21h 50m
Allegiant Air
Deal found 5/12$226
This Kiwi.com deal was found by Cheapflights users on 5/9. 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.
Mon 6/13:42 pm
MDW
-
SFB
1 stop19h 09m
Allegiant Air
Thu 6/48:50 pm
SFB
-
MDW
1 stop18h 58m
Allegiant Air
Deal found 5/9$253

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 May 13, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$163
(Kiwi.com)

One-way from

$70
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$332

Good round-trip deal

$306 or less

Good one-way deal

$162 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. 4% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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 May 13, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Orlando that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Thu 5/28

6:36 pm-11:59 pm

1 stop4h 23m

Orlando

Mon 6/1

5:30 am-10:00 am

1 stop5h 30m

$233

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Mon 6/1

3:42 pm-11:51 am

1 stop19h 09m

Orlando Sanford Intl

Thu 6/4

8:50 pm-2:48 pm

1 stop18h 58m

$253

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 6/6

8:00 am-2:10 pm

1 stop5h 10m

Orlando

Mon 6/8

9:00 am-12:20 pm

1 stop4h 20m

$259

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Fri 5/29

3:42 pm-2:22 pm

1 stop21h 40m

Orlando Sanford Intl

Sun 5/31

9:11 pm-2:52 pm

1 stop18h 41m

$261

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 5/29

8:35 pm-12:10 am

Nonstop2h 35m

Orlando

Sat 6/6

3:40 pm-7:40 pm

1 stop5h 00m

$278

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Sun 6/14

2:46 pm-5:31 pm

1 stop25h 45m

Orlando Sanford Intl

Sun 6/21

8:56 pm-7:30 pm

1 stop23h 34m

$298

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Sun 8/2

2:48 pm-5:21 pm

1 stop25h 33m

Orlando Sanford Intl

Sat 8/8

8:25 pm-1:59 pm

1 stop18h 34m

$299

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Sun 7/26

2:48 pm-8:29 pm

1 stop4h 41m

Orlando Sanford Intl

Sun 8/2

8:58 pm-2:38 pm

1 stop18h 40m

$301
Quickest round-trip

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 6/19

8:55 pm-12:30 am

Nonstop2h 35m

Orlando

Wed 6/24

11:00 am-12:45 pm

Nonstop2h 45m

$303

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 6/27

7:35 pm-11:10 pm

Nonstop2h 35m

Orlando

Wed 7/1

9:15 am-2:00 pm

1 stop5h 45m

$313

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/12

Showing 1-10 of 42 resultsSorted by cheapest first
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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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
MytripPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars
Super.comPrice Accuracy-Trust 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 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.

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?

To ensure you get the cheapest price possible for a flight from Chicago Midway Airport to Orlando, you should look to book at least 79 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, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Orlando (average of $29). Flying from Chicago Midway Airport to Orlando in August is currently the most expensive (average of $105). 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 May 13, 2026.

It’s typically best to fly out from Chicago Midway Airport to Orlando in the afternoon. Doing so could potentially save you 13% 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 May 9, 2026.

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

How much does it cost to fly round-trip from Chicago Midway Airport to Orlando?

How often are flights from Chicago to Orlando delayed?

About 15% of weekly flights between Chicago and Orlando have experienced delays in the past year, with the average delay time being 140 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, Southwest have had the lowest number of delays on this route, with just 15% 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
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Southwest and Frontier

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

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

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 May 13, 2026.
Read reviews from past customers who have flown Southwest,Delta, andFrontier 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
4,296 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Southwest
7.9
Good
4,296 reviews
Southwest
7.9
Good
4,296 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Delta
7.9
Good
8,452 reviews
Southwest
7.9
Good
4,296 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Frontier
5.6
Fair
2,952 reviews
Southwest
7.9
Good
4,296 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

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 4h 23m. Fly via Allegiant Air, Delta, or Southwest to get the fastest option. The distance between Chicago Midway Airport and Orlando is about 990 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Currently priced at $72, 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 Delta and Southwest - these airlines can fly you to your destination from $98 and $196, respectively. Frontier is priced at 73% lower than the current average price of a flight leaving 3 months from now.

  • What are the most reliable airlines from Chicago Midway Airport to Orlando?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago Midway Airport to Orlando on time: Frontier (77%), Southwest (74%), Volaris (73%).

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

    Looking at all options, your cheapest flight can be booked for $89. While the most popular route (Chicago Midway - Orlando) can be booked for $169 on average, our data indicates $319 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, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Orlando (average of $29). Flying from Chicago Midway Airport to Orlando in August is currently the most expensive (average of $105). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 3 airlines flying from Midway to Orlando

Discover the top 3 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 May 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$193FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$476FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$196Average$390FlexibilityNo cancel feeOn-time63%

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