Frontier's UpFront Plus seats guarantee an empty middle seat for extra comfort.
Frontier offers no in-flight entertainment or Wi-Fi; bring a book or pre-load entertainment.
$63+ 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Apr 21 — Apr 281
1 adult, Economy
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Find cheap flights from Orlando to Midway 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Orlando to Chicago Midway are usually found in February or September, booked 66 days in advance, depart on a Friday or Thursday and return on a Saturday
Cheap 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 April 16, 2025.
Most accurate provider | Mytrip 3 stars |
|---|---|
Most trusted provider | Mytrip 3 stars |
Round-trip from | $126 (Cheapflightsfares) |
One-way from | $67 (Cheapflightsfares) |
Popular in | March |
Cheapest in | February |
Average price | $198 |
Good round-trip deal | $154 or less |
Good one-way deal | $105 or less |
Find flight deals from Orlando to Midway
Cheapest flights from Orlando to MidwayExplore 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 April 16, 2025.
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 April 16, 2025.
This Cheapflightsfares deal was found by Cheapflights users on 4/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/810:30 amMCO - MDW
Nonstop2h 54mFrontier
Sun 5/1110:55 amMDW - MCO
Nonstop2h 43mFrontier
Deal found 4/16![Frontier logo]()
$126
This Delta deal was found by Cheapflights users on 4/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/108:00 amMCO - MDW
1 stop4h 53mDelta
Sun 5/116:38 pmMDW - MCO
1 stop5h 44mDelta
Deal found 4/15![Delta logo]()
$199
This Southwest deal was found by Cheapflights users on 4/16. 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 6/32:40 pmMCO - MDW
1 stop5h 50mSouthwest
Sat 6/77:05 pmMDW - MCO
Nonstop2h 40mSouthwest
Deal found 4/16![Southwest logo]()
$203
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 April 16, 2025.
Use the filters below to find and compare flights from Orlando Airport to Chicago Midway Airport that are best for you.
Fly from
Orlando
Fly to
Midway
Route
Depart
Return
Price
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Thu 5/8
10:30 am-12:24 pm
Nonstop2h 54m
Chicago Midway
Sun 5/11
10:55 am-2:38 pm
Nonstop2h 43m
$126
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Fri 5/16
8:50 pm-10:40 pm
Nonstop2h 50m
Chicago Midway
Tue 5/20
7:10 am-10:40 am
Nonstop2h 30m
$197
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Sat 5/10
8:00 am-11:53 am
1 stop4h 53m
Chicago Midway
Sun 5/11
6:38 pm-1:22 am
1 stop5h 44m
$199
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Thu 5/1
7:37 pm-11:39 pm
1 stop5h 02m
Chicago Midway
Sun 5/4
6:45 pm-9:26 am
2 stops13h 41m
$337
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Sun 5/25
6:20 pm-8:17 pm
Nonstop2h 57m
$63
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Sat 5/17
6:25 am-8:15 am
Nonstop2h 50m
$89
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Sun 5/25
6:00 am-12:28 pm
1 stop7h 28m
$100
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Fri 5/23
8:30 am-2:04 pm
1 stop6h 34m
$113
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Thu 6/5
8:17 am-7:46 pm
2 stops36h 29m
$127
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 April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars |
- Most accurate provider: When it comes to deals on Orlando Airport-Chicago Midway Airport flights, users find the pricing of Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on Orlando Airport-Chicago Midway Airport flight deals on Cheapflights vs. Mytrip >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 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 Orlando Airport-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
The best insider tips for Orlando Airport to Chicago Midway Airport 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 Orlando Airport to Chicago Midway Airport trip
Airlines
![Frontier]()
Frontier
![Southwest]()
Southwest
Southwest offers two free checked bags, including oversized items like skis or golf clubs.
Enjoy free in-flight entertainment with early-release movies and live TV on Southwest flights.
Airports
Our travel experts
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?
Use this chart to determine the optimal time to book a round-trip flight from Orlando to Midway. Price data was last updated on April 11, 2025.
Booking 66 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, April is the cheapest month in which you can book a flight from Orlando Airport to Chicago Midway Airport (average of $160). Flying from Orlando Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 April 16, 2025.
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 23% on your trip compared to booking a flight in the evening.
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 March 30, 2025.
Travelers seeking maximum savings on their Orlando Airport to Chicago Midway Airport flight should consider departing on Friday at noon when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Rainfall in Midway by month
Plan your trip to Midway by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.
Temperature in Midway by month
Plan your trip to Midway by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
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 April 16, 2025.
Read through reviews of airlines operating flights from Orlando to Chicago, such as Southwest, Delta and Allegiant Air. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.2
Comfort
8.0
Crew
8.6
Food
7.1
Entertainment
7.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Boarding
8.2
Comfort
8.0
Crew
8.6
Food
7.1
Entertainment
7.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Boarding
8.2
Comfort
8.0
Crew
8.6
Food
7.1
Entertainment
7.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Boarding
8.2
Comfort
8.0
Crew
8.6
Food
7.1
Entertainment
7.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Boarding
8.2
Comfort
8.0
Crew
8.6
Food
7.1
Entertainment
7.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
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.
Traveling to a place near Orlando Airport?
Book flights to Orlando Airport if you plan to visit one of these locationsMerrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton
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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.
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 April 16, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$78 | Average$171 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$184 | Average$381 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$227 | Average$307 | FlexibilityNo cancel fee | On-timeN/A |