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$95+ 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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ORL
Sep 13 — Sep 201
Sun 9/13
Sun 9/20
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Orlando are usually found in January or February, 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 August 14, 2026.

This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Sat 10/3112:03 pm -
1 stop9h 07m
Tue 11/35:29 pm -
1 stop5h 24m
Deal found 8/14$183
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:25 am -
1 stop8h 56m
Thu 11/125:29 pm -
1 stop5h 24m
Deal found 8/13$184
This Kiwi.com deal was found by Cheapflights users on 8/9. 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.
Fri 8/1411:06 am -
1 stop10h 09m
Mon 8/1710:00 am -
1 stop25h 55m
Deal found 8/9$187
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:25 am -
1 stop9h 44m
Fri 9/119:30 am -
1 stop9h 21m
Deal found 8/13$188
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Thu 8/2011:50 am -
1 stop7h 10m
Sat 8/227:57 am -
1 stop15h 50m
Deal found 8/10$189
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:15 am -
1 stop12h 13m
Tue 10/277:10 am -
1 stop15h 43m
Deal found 8/13$190
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
Sat 9/126:25 am -
1 stop9h 44m
Mon 9/145:19 pm -
1 stop7h 25m
Deal found 8/11$191
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 10/66:25 am -
1 stop9h 44m
Thu 10/83:42 pm -
1 stop7h 16m
Deal found 8/11$193
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Mon 8/176:05 am -
1 stop15h 10m
Thu 8/2010:03 am -
1 stop13h 44m
Deal found 8/10$194
This Southwest deal was found by Cheapflights users on 8/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:20 pm -
Nonstop2h 45m
Tue 9/155:25 pm -
Nonstop2h 50m
Deal found 8/13$195
This Southwest deal was found by Cheapflights users on 8/12. 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 9/96:20 pm -
Nonstop2h 45m
Fri 9/118:55 pm -
Nonstop2h 50m
Deal found 8/12$196
This Southwest deal was found by Cheapflights users on 8/10. 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 10/204:40 pm -
Nonstop2h 35m
Tue 11/109:25 am -
Nonstop2h 55m
Deal found 8/10$197

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 August 14, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$184
(Kiwi.com)

One-way from

$95
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$397

Good round-trip deal

$316 or less

Good one-way deal

$179 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. 19% potential increase in price ($78 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 August 14, 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
Quickest round-trip

ChicagoOrlando

MDW Chicago Midway - MCO Orlando

MDWMCO

Chicago Midway

Thu 10/1

8:40 pm-12:10 am

Nonstop2h 30m

Orlando

Mon 10/5

10:35 pm-12:20 am

Nonstop2h 45m

$221

ChicagoOrlando

MDW Chicago Midway - MCO Orlando

MDWMCO

Chicago Midway

Sat 10/31

8:20 am-3:55 pm

1 stop6h 35m

Orlando

Thu 11/5

3:50 pm-8:00 pm

1 stop5h 10m

$225

ChicagoOrlando

MDW Chicago Midway - MCO Orlando

MDWMCO

Chicago Midway

Tue 9/1

10:10 am-4:45 pm

1 stop5h 35m

Orlando

Sat 9/5

12:30 pm-4:45 pm

1 stop5h 15m

$226

ChicagoOrlando

MDW Chicago Midway - SFB Orlando Sanford Intl

MDWSFB

Chicago Midway

Fri 11/13

3:16 pm-6:32 pm

1 stop26h 16m

Orlando Sanford Intl

Mon 11/16

11:10 am-3:41 pm

1 stop5h 31m

$234

ChicagoOrlando

MDW Chicago Midway - MCO Orlando

MDWMCO

Chicago Midway

Fri 9/11

11:35 am-7:32 pm

1 stop6h 57m

Orlando

Sat 9/19

4:40 pm-10:44 pm

1 stop7h 04m

$236

ChicagoOrlando

MDW Chicago Midway - MCO Orlando

MDWMCO

Chicago Midway

Fri 10/16

6:40 pm-10:15 pm

Nonstop2h 35m

Orlando

Sat 10/24

6:20 am-8:10 am

Nonstop2h 50m

$240

ChicagoOrlando

MDW Chicago Midway - MCO Orlando

MDWMCO

Chicago Midway

Mon 9/28

8:15 am-1:30 pm

1 stop4h 15m

Orlando

Thu 10/1

11:35 am-2:55 pm

1 stop4h 20m

$241

ChicagoOrlando

MDW Chicago Midway - MCO Orlando

MDWMCO

Chicago Midway

Thu 9/24

1:19 pm-9:13 pm

1 stop6h 54m

Orlando

Mon 9/28

6:15 am-9:49 am

1 stop4h 34m

$273

ChicagoOrlando

MDW Chicago Midway - SFB Orlando Sanford Intl

MDWSFB

Chicago Midway

Mon 11/9

7:25 am-12:41 pm

2 stops52h 16m

Orlando Sanford Intl

Mon 11/16

11:10 am-3:41 pm

1 stop5h 31m

$274

ChicagoOrlando

MDW Chicago Midway - SFB Orlando Sanford Intl

MDWSFB

Chicago Midway

Mon 11/9

4:31 pm-10:07 am

1 stop16h 36m

Orlando Sanford Intl

Mon 11/16

11:10 am-3:41 pm

1 stop5h 31m

$279

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/10

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 August.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars
Super.comPrice Accuracy-Trust Score*3 stars
PricelinePrice Accuracy1 starTrust 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

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 $200). Flying from Chicago Midway Airport to Orlando in June is currently the most expensive (average of $460). 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 August 14, 2026.

It’s typically best to fly out from Chicago Midway Airport to Orlando in the afternoon. Doing so could potentially save you 15% on the flight price compared to flying at noon, which is usually more expensive.

Weekly flight availability from Chicago Midway Airport to Orlando

Explore weekly flight availability from Midway to Orlando. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 14, 2026.

The most flights from MDW to ORL are scheduled on a Thursday (8 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

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

Airfare is below average for this route at the moment.
Chicago Midway Airport to Orlando flights typically cost between $272 and $456 in November.
The cheapest round-trip price found within the last 5 days was $184 on Frontier (Nov 10-Nov 12).

How often are flights from Chicago to Orlando delayed?

About 16% 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, Southwest have had the lowest number of delays on this route, with just 16% of flights being delayed.

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 89 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 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 August 8, 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.

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 August 14, 2026.
Read reviews from past customers who have flown Southwest and Frontier 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
8.0
Very good
4,220 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

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
8.0
Very good
4,220 reviews
Southwest
8.0
Very good
4,220 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

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
5.6
Fair
2,694 reviews
Southwest
8.0
Very good
4,220 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

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 30m. Fly via Southwest, Allegiant Air, or Delta 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 $65, 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. Check Cheapflights for deals on Southwest for as low as $210. Frontier is priced at 80% 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 $118. While the most popular route (Chicago Midway - Orlando) can be booked for $177 on average, our data indicates $308 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 $200). Flying from Chicago Midway Airport to Orlando in June is currently the most expensive (average of $460). 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 2 airlines flying from Midway to Orlando

Discover the top 2 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 August 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$65Average$203FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$210Average$419FlexibilityNo cancel feeOn-time63%

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