$102+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Jul 31 — Aug 71
Round-trip
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 October, booked 86 days in advance, depart on a Friday or Saturday and return on a Thursday
Cheap flight deals from Orlando to Midway
Cheapest
Best
Last-minute
One-way
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 July 1, 2026.
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 July 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:24 pm
MCO
- MDW
1 stop5h 39m
Frontier
Wed 8/124:45 pm
MDW
- MCO
1 stop6h 14m
Frontier
Deal found 6/28![Frontier logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 8/115:15 am
MCO
- MDW
1 stop5h 36m
Frontier
Tue 8/1811:50 am
MDW
- MCO
1 stop5h 43m
Frontier
Deal found 6/27![Frontier logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 8/45:24 pm
MCO
- MDW
1 stop5h 39m
Frontier
Wed 8/511:06 am
MDW
- MCO
1 stop6h 27m
Frontier
Deal found 6/27![Frontier logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 6/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:15 am
MCO
- MDW
1 stop5h 36m
Frontier
Wed 8/1911:50 am
MDW
- MCO
1 stop5h 43m
Frontier
Deal found 6/29![Frontier logo]()
$208
This Frontier deal was found by Cheapflights users on 6/30. 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.
Tue 9/15:23 pm
MCO
- MDW
1 stop6h 24m
Frontier
Wed 9/26:05 am
MDW
- MCO
1 stop11h 28m
Frontier
Deal found 6/30![Frontier logo]()
$210
This Frontier deal was found by Cheapflights users on 6/30. 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.
Tue 8/45:24 pm
MCO
- MDW
1 stop5h 39m
Frontier
Tue 8/1111:06 am
MDW
- MCO
1 stop10h 09m
Frontier
Deal found 6/30![Frontier logo]()
$211
This Southwest deal was found by Cheapflights users on 6/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:00 am
MCO
- MDW
Nonstop2h 50m
Southwest
Wed 7/224:40 pm
MDW
- MCO
Nonstop2h 45m
Southwest
Deal found 6/29![Southwest logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 10/85:29 pm
MCO
- MDW
1 stop5h 29m
Frontier
Tue 10/136:40 am
MDW
- MCO
1 stop6h 57m
Frontier
Deal found 6/27![Frontier logo]()
$219
This Super.com deal was found by Cheapflights users on 6/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/295:20 am
MCO
- MDW
1 stop6h 47m
Frontier
Wed 8/511:06 am
MDW
- MCO
1 stop6h 27m
Frontier
Deal found 6/30![Frontier logo]()
$220
This Southwest deal was found by Cheapflights users on 6/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:25 pm
MCO
- MDW
Nonstop2h 50m
Southwest
Mon 8/107:50 pm
MDW
- MCO
Nonstop2h 30m
Southwest
Deal found 6/29![Southwest logo]()
$221
Best flights from Orlando to MidwayDiscover carefully curated flight deals from Orlando to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 1, 2026.
Discover carefully curated flight deals from Orlando to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 1, 2026.
This Southwest deal was found by Cheapflights users on 6/30. 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.
Sat 8/229:10 am
MCO
- MDW
Nonstop2h 50m
Southwest
Tue 8/2512:20 pm
MDW
- MCO
Nonstop2h 40m
Southwest
Deal found 6/30![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 6/30. 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.
Wed 9/211:05 am
MCO
- MDW
1 stop5h 39m
Delta
Sat 9/54:39 pm
MDW
- MCO
1 stop6h 25m
Delta
Deal found 6/30![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 6/28. 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 8/129:00 am
MCO
- MDW
1 stop4h 05m
Southwest
Wed 8/196:15 am
MDW
- MCO
Nonstop2h 30m
Southwest
Deal found 6/28![Southwest logo]()
$223
This Delta deal was found by Cheapflights users on 6/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2412:38 pm
MCO
- MDW
1 stop6h 55m
Delta
Thu 10/19:29 am
MDW
- MCO
1 stop4h 31m
Delta
Deal found 6/28![Delta logo]()
$245
This Southwest deal was found by Cheapflights users on 6/30. 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 8/119:00 am
MCO
- MDW
1 stop4h 05m
Southwest
Sat 8/157:50 am
MDW
- MCO
1 stop4h 05m
Southwest
Deal found 6/30![Southwest logo]()
$228
This Southwest deal was found by Cheapflights users on 6/27. 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 7/284:40 pm
MCO
- MDW
1 stop4h 10m
Southwest
Tue 8/47:40 am
MDW
- MCO
2 stops5h 55m
Southwest
Deal found 6/27![Southwest logo]()
$238
This Southwest deal was found by Cheapflights users on 6/27. 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.
Thu 9/37:10 am
MCO
- MDW
1 stop5h 15m
Southwest
Sat 9/59:20 am
MDW
- MCO
1 stop4h 50m
Southwest
Deal found 6/27![Southwest logo]()
$243
This Southwest deal was found by Cheapflights users on 6/26. 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 8/261:00 pm
MCO
- MDW
Nonstop2h 45m
Southwest
Fri 8/285:00 am
MDW
- MCO
Nonstop2h 30m
Southwest
Deal found 6/26![Southwest logo]()
$278
This Southwest deal was found by Cheapflights users on 6/26. 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.
Thu 9/38:15 am
MCO
- MDW
Nonstop2h 45m
Southwest
Mon 9/77:30 am
MDW
- MCO
1 stop5h 40m
Southwest
Deal found 6/26![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 6/30. 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.
Thu 8/138:55 pm
MCO
- MDW
Nonstop2h 45m
Southwest
Sun 8/1610:15 am
MDW
- MCO
1 stop5h 10m
Southwest
Deal found 6/30![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 6/30. 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.
Thu 8/67:10 am
MCO
- MDW
1 stop5h 15m
Southwest
Sun 8/98:05 pm
MDW
- MCO
Nonstop2h 30m
Southwest
Deal found 6/30![Southwest logo]()
$299
Last-minute flights from Orlando to MidwayDiscover last-minute flight deals from Orlando to Midway. Data last updated July 1, 2026 and is based on user searches.
Discover last-minute flight deals from Orlando to Midway. Data last updated July 1, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:00 am
MCO
- MDW
Nonstop2h 50m
Southwest
Wed 7/224:40 pm
MDW
- MCO
Nonstop2h 45m
Southwest
Deal found 6/29![Southwest logo]()
$217
This Frontier deal was found by Cheapflights users on 6/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/215:20 am
MCO
- MDW
1 stop6h 47m
Frontier
Wed 7/296:05 am
MDW
- MCO
1 stop11h 28m
Frontier
Deal found 6/28![Frontier logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/225:24 pm
MCO
- MDW
1 stop5h 39m
Frontier
Wed 7/2912:11 pm
MDW
- MCO
1 stop5h 22m
Frontier
Deal found 6/28![Frontier logo]()
$226
This Southwest deal was found by Cheapflights users on 6/30. 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 7/288:00 am
MCO
- MDW
Nonstop2h 50m
Southwest
Tue 8/410:20 am
MDW
- MCO
1 stop6h 05m
Southwest
Deal found 6/30![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 6/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2810:05 am
MCO
- MDW
1 stop7h 10m
Delta
Sat 8/16:00 am
MDW
- MCO
1 stop6h 00m
Delta
Deal found 6/29![Delta logo]()
$237
This Super.com deal was found by Cheapflights users on 7/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/295:20 am
MCO
- MDW
1 stop6h 47m
Frontier
Wed 8/511:06 am
MDW
- MCO
1 stop6h 27m
Frontier
Deal found 7/1![Frontier logo]()
$220
This Frontier deal was found by Cheapflights users on 7/1. 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.
Thu 7/303:18 pm
MCO
- MDW
1 stop7h 45m
Frontier
Tue 8/412:11 pm
MDW
- MCO
1 stop9h 04m
Frontier
Deal found 7/1![Frontier logo]()
$239
This Frontier deal was found by Cheapflights users on 7/1. 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 7/313:18 pm
MCO
- MDW
1 stop7h 45m
Frontier
Tue 8/412:11 pm
MDW
- MCO
1 stop9h 04m
Frontier
Deal found 7/1![Frontier logo]()
$240
One-way flights from Orlando to MidwaySearch for one-way flight options from Orlando to Midway. Find affordable one-way fares based on user searches. Data last updated July 1, 2026.
Search for one-way flight options from Orlando to Midway. Find affordable one-way fares based on user searches. Data last updated July 1, 2026.
This iWofly deal was found by Cheapflights users on 6/27. 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 iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:24 pm
MCO
- MDW
1 stop5h 39m
Frontier
Deal found 6/27![Frontier logo]()
$102
This Super.com deal was found by Cheapflights users on 6/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/265:24 am
MCO
- MDW
1 stop6h 31m
Frontier
Deal found 6/28![Frontier logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 9/115:29 pm
MCO
- MDW
1 stop18h 29m
Frontier
Deal found 6/30![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/265:29 pm
MCO
- MDW
1 stop5h 29m
Frontier
Deal found 6/28![Frontier logo]()
$107
This Trip.com deal was found by Cheapflights users on 6/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:23 pm
MCO
- MDW
1 stop6h 24m
Frontier
Deal found 6/28![Frontier logo]()
$108
This Southwest deal was found by Cheapflights users on 6/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/211:30 pm
MCO
- MDW
Nonstop2h 45m
Southwest
Deal found 6/29![Southwest logo]()
$109
This Super.com deal was found by Cheapflights users on 6/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/295:24 pm
MCO
- MDW
1 stop5h 39m
Frontier
Deal found 6/30![Frontier logo]()
$113
This WAYA deal was found by Cheapflights users on 7/1. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1710:29 am
MCO
- MDW
1 stop5h 30m
Allegiant Air
Deal found 7/1![Allegiant Air logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 10/15:29 pm
MCO
- MDW
1 stop29h 29m
Frontier
Deal found 7/1![Frontier logo]()
$118
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 July 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $203 (Kiwi.com) |
One-way from | $102 (iWofly) |
Popular in | June |
Cheapest in | February |
Average price | $292 |
Good round-trip deal | $306 or less |
Good one-way deal | $172 or less |
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 July 1, 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
Cheapest round-trip
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Sat 8/22
9:10 am-11:00 am
Nonstop2h 50m
Chicago Midway
Tue 8/25
12:20 pm-4:00 pm
Nonstop2h 40m
$217
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Wed 8/12
9:00 am-12:05 pm
1 stop4h 05m
Chicago Midway
Wed 8/19
6:15 am-9:45 am
Nonstop2h 30m
$223
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Tue 8/11
9:00 am-12:05 pm
1 stop4h 05m
Chicago Midway
Sat 8/15
7:50 am-12:55 pm
1 stop4h 05m
$228
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Wed 9/2
11:05 am-3:44 pm
1 stop5h 39m
Chicago Midway
Sat 9/5
4:39 pm-12:04 am
1 stop6h 25m
$237
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Tue 7/28
4:40 pm-7:50 pm
1 stop4h 10m
Chicago Midway
Tue 8/4
7:40 am-2:35 pm
2 stops5h 55m
$238
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Thu 9/3
7:10 am-11:25 am
1 stop5h 15m
Chicago Midway
Sat 9/5
9:20 am-3:10 pm
1 stop4h 50m
$243
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Thu 9/24
12:38 pm-6:33 pm
1 stop6h 55m
Chicago Midway
Thu 10/1
9:29 am-3:00 pm
1 stop4h 31m
$245
Quickest round-trip
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Wed 8/26
1:00 pm-2:45 pm
Nonstop2h 45m
Chicago Midway
Fri 8/28
5:00 am-8:30 am
Nonstop2h 30m
$278
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Thu 9/3
8:15 am-10:00 am
Nonstop2h 45m
Chicago Midway
Mon 9/7
7:30 am-2:10 pm
1 stop5h 40m
$292
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Thu 8/13
8:55 pm-10:40 pm
Nonstop2h 45m
Chicago Midway
Sun 8/16
10:15 am-4:25 pm
1 stop5h 10m
$299
Showing 1-10 of 22 resultsSorted by cheapest first
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 July.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- 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.
MCO-MDW
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
Prices
Delays
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, February is the cheapest month in which you can book a flight from Orlando Airport to Chicago Midway Airport (average of $164). Flying from Orlando Airport to Chicago Midway Airport in June is currently the most expensive (average of $417). 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 July 1, 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 June 27, 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 often are flights from Orlando to Chicago delayed?
About 23% of weekly flights between Orlando and Chicago have experienced delays in the past year, with the average delay time being 132 minutes.
What is the most punctual flight time for Orlando to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Wednesday 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 Orlando to Chicago flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 23% of flights being delayed.
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
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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 July 1, 2026.
See what other customers who have flown with Southwest and Frontier 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.
Crew
8.6
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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 Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Hammond
Lansing
Merrillville
Valparaiso
Porter
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Top 2 airlines flying from Orlando to Midway
Discover the top 2 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 July 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$167 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$159 | Average$313 | FlexibilityNo cancel fee | On-time63% |