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$61+ 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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ORL
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 57 days in advance, depart on a Thursday or Friday 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 July 30, 2025.

Round-trip from

$102
(Frontier)

One-way from

$61
(Cheapflightsfares)

Popular in

October

Cheapest in

September

Average price

$224

Good round-trip deal

$153 or less

Good one-way deal

$105 or less
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. 0% potential increase in price ($1 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 30, 2025.

This Frontier deal was found by Cheapflights users on 7/29. 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.
Fri 9/199:48 amMDW - MCO
Nonstop2h 40mFrontier
Sun 9/217:25 amMCO - MDW
Nonstop2h 53mFrontier
Deal found 7/29$102
This Southwest deal was found by Cheapflights users on 7/28. 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 8/276:15 amMDW - MCO
Nonstop2h 30mSouthwest
Wed 9/310:05 amMCO - MDW
Nonstop2h 45mSouthwest
Deal found 7/28$157
This Mytrip deal was found by Cheapflights users on 7/29. 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.
Fri 8/229:32 amMDW - SFB
1 stop10h 12mAllegiant Air
Mon 8/2510:55 amSFB - MDW
1 stop5h 07mAllegiant Air
Deal found 7/29$202

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 July 30, 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

Fri 9/19

9:48 am-1:28 pm

Nonstop2h 40m

Orlando

Sun 9/21

7:25 am-9:18 am

Nonstop2h 53m

$102

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 8/27

6:15 am-9:45 am

Nonstop2h 30m

Orlando

Wed 9/3

10:05 am-11:50 am

Nonstop2h 45m

$157

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Fri 8/22

9:32 am-8:44 pm

1 stop10h 12m

Orlando Sanford Intl

Mon 8/25

10:55 am-3:02 pm

1 stop5h 07m

$202

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 8/17

8:35 am-12:20 pm

Nonstop2h 45m

$61

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 9/2

4:45 pm-8:25 pm

Nonstop2h 40m

$79

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Fri 8/15

7:07 pm-9:47 am

1 stop13h 40m

$98

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 8/25

9:30 am-4:13 pm

1 stop5h 43m

$105

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 8/11

1:11 pm-8:43 pm

1 stop6h 32m

$107

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

The best insider tips for Chicago Midway Airport to Orlando flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Orlando trip
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
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

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 July 25, 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 57 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 $288). 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 July 30, 2025.

It’s typically best to fly out from Chicago Midway Airport to Orlando at noon. Doing so could potentially save you 12% on the flight price compared to flying in the morning, 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 July 27, 2025.

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

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 July 30, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Allegiant Air 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
4,241 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

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
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

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
7.2
Good
703 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

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
5.9
Fair
3,237 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

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 $102, 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 Allegiant Air - these airlines can fly you to your destination from $157 and $202, respectively. Frontier is priced at 61% 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 $61. However, be on the lookout for offers from Southwest and Allegiant Air, 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 $66. While the most popular route (Chicago Midway - Orlando) can be booked for $78 on average our data indicates $181 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 $288). 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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$93Average$193FlexibilityNo cancel feeOn-time65%
FrontierCheapest$106Average$222FlexibilityNo cancel feeOn-time62%
DeltaCheapest$196Average$304FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$216Average$395FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$248Average$364FlexibilityNo cancel feeOn-time69%

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