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Midway

$84+ Cheap flights from Orlando (MCO) to Midway (MDW)

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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Jun 13 — Jun 201
Sat 6/13
Sat 6/20
1 adult, Economy
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Find cheap flights from Orlando to Midway with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Orlando to Chicago Midway are usually found in November or September, booked 86 days in advance, depart on a Friday or Saturday and return on a Thursday

Cheap flight deals from Orlando to Midway

Cheapest flights from Orlando to Midway
Explore the most affordable flight options available from Orlando to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 14, 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 8/185:31 am
MCO
-
MDW
1 stop6h 41m
Frontier
Wed 8/1912:04 pm
MDW
-
MCO
1 stop9h 05m
Frontier
Deal found 5/12$132
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.
Thu 8/135:10 pm
MCO
-
MDW
1 stop5h 58m
Frontier
Wed 8/1912:04 pm
MDW
-
MCO
1 stop9h 05m
Frontier
Deal found 5/12$148
This Southwest deal was found by Cheapflights users on 5/13. 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 7/87:10 am
MCO
-
MDW
Nonstop2h 50m
Southwest
Wed 7/154:40 pm
MDW
-
MCO
Nonstop2h 45m
Southwest
Deal found 5/13$169
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 9/15:10 pm
MCO
-
MDW
1 stop6h 01m
Frontier
Wed 9/3012:03 pm
MDW
-
MCO
1 stop9h 07m
Frontier
Deal found 5/12$171
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 6/165:25 am
MCO
-
MDW
1 stop17h 46m
Frontier
Tue 6/3012:27 pm
MDW
-
MCO
1 stop8h 42m
Frontier
Deal found 5/10$177
This Southwest deal was found by Cheapflights users on 5/13. 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.
Tue 6/238:00 am
MCO
-
MDW
Nonstop2h 50m
Southwest
Wed 6/242:35 pm
MDW
-
MCO
1 stop5h 25m
Southwest
Deal found 5/13$179
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 6/164:40 pm
MCO
-
MDW
1 stop4h 10m
Southwest
Wed 6/242:35 pm
MDW
-
MCO
1 stop5h 25m
Southwest
Deal found 5/12$184
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 8/115:25 am
MCO
-
MDW
1 stop6h 42m
Frontier
Thu 8/1312:11 pm
MDW
-
MCO
1 stop6h 28m
Frontier
Deal found 5/11$186
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.
Mon 8/1010:59 am
MCO
-
MDW
1 stop5h 00m
Multiple Airlines
Wed 8/1912:04 pm
MDW
-
MCO
1 stop9h 05m
Multiple Airlines
Deal found 5/11$187

Find flight deals from Orlando to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Orlando (MCO) to Midway (MDW). 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 14, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$132
(Kiwi.com)

One-way from

$84
(Kiwi.com)

Popular in

April

Cheapest in

November

Average price

$297

Good round-trip deal

$206 or less

Good one-way deal

$162 or less
Provider with most accurate pricing for Orlando-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Orlando-Chicago Midway flights.
Search Deals
From Orlando to Chicago Midway
Search Deals
One-way flight from Orlando to Chicago Midway
Search Deals
Highest demand for flights based on searches. 26% potential increase in price ($79 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($17 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 Orlando to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Orlando to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Orlando to Midway 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 14, 2026.
Use the filters below to find and compare flights from Orlando Airport to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 7/8

4:40 pm-7:50 pm

1 stop4h 10m

Chicago Midway

Wed 7/15

3:00 pm-7:55 pm

1 stop3h 55m

$180

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 8/11

6:15 am-9:59 am

1 stop4h 44m

Chicago Midway

Tue 8/18

6:05 am-12:00 pm

1 stop4h 55m

$197

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 8/5

9:00 am-12:05 pm

1 stop4h 05m

Chicago Midway

Wed 8/19

7:40 am-2:35 pm

2 stops5h 55m

$245

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 6/26

6:50 am-10:00 am

1 stop4h 10m

Chicago Midway

Wed 7/1

4:40 pm-8:25 pm

Nonstop2h 45m

$309

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 7/21

4:40 pm-7:50 pm

1 stop4h 10m

Chicago Midway

Fri 7/24

6:35 pm-10:10 pm

Nonstop2h 35m

$309

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 6/17

4:40 pm-7:50 pm

1 stop4h 10m

Chicago Midway

Wed 6/24

5:30 pm-9:15 pm

Nonstop2h 45m

$309

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 6/20

5:45 pm-10:17 pm

1 stop5h 32m

Chicago Midway

Wed 7/8

6:00 am-12:00 pm

1 stop5h 00m

$327
Quickest round-trip

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 7/3

10:55 pm-12:40 am

Nonstop2h 45m

Chicago Midway

Mon 7/6

8:55 pm-12:30 am

Nonstop2h 35m

$327

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 6/4

10:55 pm-12:40 am

Nonstop2h 45m

Chicago Midway

Sun 6/7

8:35 pm-12:10 am

Nonstop2h 35m

$330

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 5/29

10:20 pm-12:15 am

Nonstop2h 55m

Chicago Midway

Sun 5/31

8:50 pm-12:25 am

Nonstop2h 35m

$339

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/12

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Orlando to Midway

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 Orlando to Midway in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Super.comPrice Accuracy-Trust Score*3 stars
MytripPrice Accuracy2 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 Orlando Airport-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Orlando Airport-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Orlando Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Orlando Airport-Chicago Midway Airport 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 Orlando Airport-Chicago Midway Airport 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 Orlando to Midway

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

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

Booking 85 days in advance of your planned departure date is, on average, the best time to get cheap flights from Orlando Airport to Chicago Midway Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, November is the cheapest month in which you can book a flight from Orlando Airport to Chicago Midway Airport (average of $159). Flying from Orlando Airport to Chicago Midway Airport in April is currently the most expensive (average of $397). 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 MCO to MDW?

Find hourly flight availability from Orlando to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 14, 2026.

A simple way to save on the total cost of your ticket is to fly from Orlando Airport to Chicago Midway Airport at noon. If you’re flexible enough to do this you can expect to save up to 27% on your trip compared to booking a flight in the morning.

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

Use this chart to determine the cheapest time to fly round-trip from Orlando to Midway. Price data was last updated on May 9, 2026.

Travelers seeking maximum savings on their Orlando Airport to Chicago Midway Airport flight should consider departing on Saturday at noon when fares are most often at their lowest. Monday evenings 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 Orlando Airport to Chicago Midway Airport?

The best insider tips for Orlando Airport to Chicago Midway Airport 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 Orlando Airport to Chicago Midway Airport trip
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Frontier and Southwest

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 Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated May 14, 2026.
See what other customers who have flown with Southwest,Delta, andFrontier from Orlando Airport to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,299 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,299 reviews
Southwest
8.0
Very good
4,299 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,452 reviews
Southwest
8.0
Very good
4,299 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,953 reviews
Southwest
8.0
Very good
4,299 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

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

    A quick flight from Orlando Airport to Chicago Midway Airport can take about 4h 10m. Southwest provides one of the quickest options available for as low as $180. Airlines will cover a distance of 990 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Cheapflights users have booked flights from Orlando Airport to Chicago Midway Airport round-trip from $68. Other airlines that can offer you cheap pricing are Southwest, from $159, and Delta, from $173. Frontier is currently priced 69% below the average price you’ll pay for this route.

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

    Consider Frontier (70%), Southwest (66%) or Volaris (56%) when booking your flight. These represent the most reliable airlines when flying from Orlando Airport to Chicago Midway Airport.

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

    Looking at all options, your cheapest flight can be booked for $84. While the most popular route (Orlando - Chicago Midway) can be booked for $169 on average, our data indicates $284 when flying from Orlando Airport to Chicago Midway Airport.

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Orlando Airport to Chicago Midway Airport (average of $159). Flying from Orlando Airport to Chicago Midway Airport in April is currently the most expensive (average of $397). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Orlando to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Orlando to O'Hare Intl flights
Orlando Sanford Intl to Rockford flights

Top 3 airlines flying from Orlando to Midway

Discover the top 3 airlines that operate flights from Orlando to Midway. 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 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$68Average$158FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$159Average$298FlexibilityNo cancel feeOn-time63%
DeltaCheapest$173Average$196FlexibilityNo cancel feeOn-timeN/A

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