$51+ 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 3/18. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Mar 16 — Mar 231
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 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
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 February 14, 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 February 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
Fri 3/69:51 pm
MCO
- MDW
Nonstop3h 00m
Frontier
Sun 3/88:00 am
MDW
- MCO
Nonstop2h 49m
Frontier
Deal found 2/12![Frontier logo]()
$85
This Super.com deal was found by Cheapflights users on 2/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:05 am
MCO
- MDW
Nonstop2h 59m
Frontier
Mon 5/49:14 am
MDW
- MCO
Nonstop2h 49m
Frontier
Deal found 2/12![Frontier logo]()
$87
This Frontier deal was found by Cheapflights users on 2/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:05 am
MCO
- MDW
Nonstop2h 59m
Frontier
Mon 5/189:14 am
MDW
- MCO
Nonstop2h 49m
Frontier
Deal found 2/10![Frontier logo]()
$88
This Trip.com deal was found by Cheapflights users on 2/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/69:51 pm
MCO
- MDW
Nonstop3h 00m
Frontier
Mon 3/99:51 pm
MDW
- MCO
Nonstop2h 47m
Frontier
Deal found 2/13![Frontier logo]()
$89
This Super.com deal was found by Cheapflights users on 2/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/139:51 pm
MCO
- MDW
Nonstop3h 00m
Frontier
Mon 3/169:51 pm
MDW
- MCO
Nonstop2h 47m
Frontier
Deal found 2/10![Frontier logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Sat 5/22:13 pm
MCO
- MDW
Nonstop3h 00m
Frontier
Sun 5/107:30 am
MDW
- MCO
1 stop8h 14m
Frontier
Deal found 2/10![Frontier logo]()
$92
This Super.com deal was found by Cheapflights users on 2/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:20 pm
MCO
- MDW
Nonstop3h 06m
Frontier
Mon 3/96:15 am
MDW
- MCO
Nonstop2h 50m
Frontier
Deal found 2/13![Frontier logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 5/22:13 pm
MCO
- MDW
Nonstop3h 00m
Frontier
Tue 5/57:30 am
MDW
- MCO
1 stop8h 14m
Frontier
Deal found 2/11![Frontier logo]()
$97
This Expedia deal was found by Cheapflights users on 2/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/147:42 pm
MCO
- MDW
Nonstop3h 03m
Frontier
Mon 3/169:51 pm
MDW
- MCO
Nonstop2h 47m
Frontier
Deal found 2/10![Frontier logo]()
$98
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 February 14, 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 February 14, 2026.
This Frontier deal was found by Cheapflights users on 2/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/146:05 am
MCO
- MDW
Nonstop2h 59m
Frontier
Sun 5/179:14 am
MDW
- MCO
Nonstop2h 49m
Frontier
Deal found 2/10![Frontier logo]()
$88
This Southwest deal was found by Cheapflights users on 2/10. 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.
Wed 5/67:35 pm
MCO
- MDW
Nonstop2h 50m
Southwest
Mon 5/114:35 pm
MDW
- MCO
Nonstop2h 40m
Southwest
Deal found 2/10![Southwest logo]()
$177
This Expedia deal was found by Cheapflights users on 2/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/310:28 am
MCO
- MDW
1 stop9h 39m
Frontier
Mon 3/99:51 pm
MDW
- MCO
Nonstop2h 47m
Frontier
Deal found 2/10![Frontier logo]()
$107
This Delta deal was found by Cheapflights users on 2/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/176:00 am
MCO
- MDW
1 stop7h 29m
Delta
Tue 3/176:07 pm
MDW
- MCO
1 stop4h 59m
Delta
Deal found 2/13![Delta logo]()
$217
This Frontier deal was found by Cheapflights users on 2/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/174:05 pm
MCO
- MDW
Nonstop3h 08m
Frontier
Mon 3/239:51 pm
MDW
- MCO
Nonstop2h 47m
Frontier
Deal found 2/13![Frontier logo]()
$114
This Frontier deal was found by Cheapflights users on 2/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/139:51 pm
MCO
- MDW
Nonstop3h 00m
Frontier
Wed 3/186:05 am
MDW
- MCO
1 stop7h 20m
Frontier
Deal found 2/10![Frontier logo]()
$123
This Southwest deal was found by Cheapflights users on 2/13. 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.
Thu 5/146:50 pm
MCO
- MDW
Nonstop2h 50m
Southwest
Sun 5/176:35 pm
MDW
- MCO
Nonstop2h 40m
Southwest
Deal found 2/13![Southwest logo]()
$197
This Frontier deal was found by Cheapflights users on 2/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/83:25 pm
MCO
- MDW
1 stop7h 54m
Frontier
Thu 4/92:56 pm
MDW
- MCO
1 stop8h 23m
Frontier
Deal found 2/10![Frontier logo]()
$160
This Travelocity deal was found by Cheapflights users on 2/11. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/113:25 pm
MCO
- MDW
1 stop7h 54m
Frontier
Wed 3/186:05 am
MDW
- MCO
1 stop7h 20m
Frontier
Deal found 2/11![Frontier logo]()
$160
This Expedia deal was found by Cheapflights users on 2/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/239:00 am
MCO
- MDW
1 stop11h 31m
Frontier
Mon 4/276:00 am
MDW
- MCO
1 stop6h 37m
Frontier
Deal found 2/13![Frontier logo]()
$160
This Frontier deal was found by Cheapflights users on 2/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/83:18 pm
MCO
- MDW
1 stop8h 03m
Frontier
Mon 5/114:09 pm
MDW
- MCO
1 stop7h 42m
Frontier
Deal found 2/12![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 2/13. 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 3/174:05 pm
MCO
- MDW
Nonstop3h 08m
Frontier
Thu 3/192:41 pm
MDW
- MCO
1 stop8h 38m
Frontier
Deal found 2/13![Frontier logo]()
$199
Last-minute flights from Orlando to MidwayDiscover last-minute flight deals from Orlando to Midway. Data last updated February 14, 2026 and is based on user searches.
Discover last-minute flight deals from Orlando to Midway. Data last updated February 14, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 2/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2712:20 pm
MCO
- MDW
Nonstop3h 06m
Frontier
Mon 3/29:22 pm
MDW
- MCO
Nonstop2h 47m
Frontier
Deal found 2/13![Frontier logo]()
$109
This Expedia deal was found by Cheapflights users on 2/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/310:28 am
MCO
- MDW
1 stop9h 39m
Frontier
Mon 3/99:51 pm
MDW
- MCO
Nonstop2h 47m
Frontier
Deal found 2/10![Frontier logo]()
$107
This Super.com deal was found by Cheapflights users on 2/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:20 pm
MCO
- MDW
Nonstop3h 06m
Frontier
Mon 3/96:15 am
MDW
- MCO
Nonstop2h 50m
Frontier
Deal found 2/13![Frontier logo]()
$94
This Super.com deal was found by Cheapflights users on 2/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:48 pm
MCO
- MDW
Nonstop3h 05m
Frontier
Mon 3/96:15 am
MDW
- MCO
Nonstop2h 50m
Frontier
Deal found 2/12![Frontier logo]()
$85
This Super.com deal was found by Cheapflights users on 2/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/139:51 pm
MCO
- MDW
Nonstop3h 00m
Frontier
Mon 3/169:51 pm
MDW
- MCO
Nonstop2h 47m
Frontier
Deal found 2/10![Frontier logo]()
$91
This Expedia deal was found by Cheapflights users on 2/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/147:42 pm
MCO
- MDW
Nonstop3h 03m
Frontier
Mon 3/169:51 pm
MDW
- MCO
Nonstop2h 47m
Frontier
Deal found 2/10![Frontier logo]()
$98
This Frontier deal was found by Cheapflights users on 2/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/174:05 pm
MCO
- MDW
Nonstop3h 08m
Frontier
Tue 3/244:33 pm
MDW
- MCO
Nonstop2h 46m
Frontier
Deal found 2/11![Frontier logo]()
$106
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 February 14, 2026.
Search for one-way flight options from Orlando to Midway. Find affordable one-way fares based on user searches. Data last updated February 14, 2026.
This Trip.com deal was found by Cheapflights users on 2/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/184:05 pm
MCO
- MDW
Nonstop3h 08m
Frontier
Deal found 2/10![Frontier logo]()
$51
This Frontier deal was found by Cheapflights users on 2/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/611:05 am
MCO
- MDW
Nonstop3h 03m
Frontier
Deal found 2/14![Frontier logo]()
$52
This Trip.com deal was found by Cheapflights users on 2/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/174:05 pm
MCO
- MDW
Nonstop3h 08m
Frontier
Deal found 2/13![Frontier logo]()
$53
This Kiwi.com deal was found by Cheapflights users on 2/14. 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 3/77:42 pm
MCO
- MDW
Nonstop3h 03m
Frontier
Deal found 2/14![Frontier logo]()
$56
This Expedia deal was found by Cheapflights users on 2/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/241:31 pm
MCO
- MDW
Nonstop3h 02m
Frontier
Deal found 2/14![Frontier logo]()
$57
This Frontier deal was found by Cheapflights users on 2/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2712:20 pm
MCO
- MDW
Nonstop3h 06m
Frontier
Deal found 2/13![Frontier logo]()
$58
This WAYA deal was found by Cheapflights users on 2/10. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/410:28 am
MCO
- MDW
1 stop9h 39m
Frontier
Deal found 2/10![Frontier logo]()
$63
This Super.com deal was found by Cheapflights users on 2/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2612:20 pm
MCO
- MDW
Nonstop3h 06m
Frontier
Deal found 2/12![Frontier logo]()
$64
This WAYA deal was found by Cheapflights users on 2/10. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/113:25 pm
MCO
- MDW
1 stop7h 54m
Frontier
Deal found 2/10![Frontier logo]()
$65
This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
Wed 4/291:15 pm
MCO
- MDW
1 stop24h 45m
Frontier
Deal found 2/11![Frontier logo]()
$66
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 February 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $85 (Super.com) |
One-way from | $51 (Trip.com) |
Popular in | March |
Cheapest in | November |
Average price | $197 |
Good round-trip deal | $110 or less |
Good one-way deal | $101 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 February 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
Orlando
Fly to
Midway
Route
Depart
Return
Price
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Thu 5/14
6:05 am-8:04 am
Nonstop2h 59m
Chicago Midway
Sun 5/17
9:14 am-1:03 pm
Nonstop2h 49m
$88
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Tue 3/3
10:28 am-7:07 pm
1 stop9h 39m
Chicago Midway
Mon 3/9
9:51 pm-1:38 am
Nonstop2h 47m
$107
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Tue 3/17
4:05 pm-6:13 pm
Nonstop3h 08m
Chicago Midway
Mon 3/23
9:51 pm-1:38 am
Nonstop2h 47m
$114
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Fri 3/13
9:51 pm-11:51 pm
Nonstop3h 00m
Chicago Midway
Wed 3/18
6:05 am-2:25 pm
1 stop7h 20m
$123
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Wed 4/8
3:25 pm-10:19 pm
1 stop7h 54m
Chicago Midway
Thu 4/9
2:56 pm-12:19 am
1 stop8h 23m
$160
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Wed 3/11
3:25 pm-10:19 pm
1 stop7h 54m
Chicago Midway
Wed 3/18
6:05 am-2:25 pm
1 stop7h 20m
$160
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Thu 4/23
9:00 am-7:31 pm
1 stop11h 31m
Chicago Midway
Mon 4/27
6:00 am-1:37 pm
1 stop6h 37m
$160
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Fri 5/8
3:18 pm-10:21 pm
1 stop8h 03m
Chicago Midway
Mon 5/11
4:09 pm-12:51 am
1 stop7h 42m
$160
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Wed 5/6
7:35 pm-9:25 pm
Nonstop2h 50m
Chicago Midway
Mon 5/11
4:35 pm-8:15 pm
Nonstop2h 40m
$177
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Thu 5/14
6:50 pm-8:40 pm
Nonstop2h 50m
Chicago Midway
Sun 5/17
6:35 pm-10:15 pm
Nonstop2h 40m
$197
Showing 1-10 of 23 results
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 February.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy1 star | 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?
Use this chart to determine the optimal time to book a round-trip flight from Orlando to Midway. Price data was last updated on February 6, 2026.
Booking 86 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, January is the cheapest month in which you can book a flight from Orlando Airport to Chicago Midway Airport (average of $55). Flying from Orlando Airport to Chicago Midway Airport in March is currently the most expensive (average of $169). 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 February 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 February 7, 2026.
Travelers seeking maximum savings on their Orlando Airport to Chicago Midway Airport flight should consider departing on Thursday at noon when fares are most often at their lowest. Tuesday at noon 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 20% of weekly flights between Orlando and Chicago have experienced delays in the past year, with the average delay time being 135 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?
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 Orlando to Chicago flights?
Over the last year, Frontier have had the lowest number of delays on this route, with just 18% 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 February 14, 2026.
See what other customers who have flown with Southwest, Delta, 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.
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
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 Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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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 February 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$160 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$99 | Average$196 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$159 | Average$294 | FlexibilityNo cancel fee | On-time63% |