$98+ Cheap flights from Midway (MDW) to Orlando (ORL)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ORL
Oct 29 — Nov 51
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Orlando 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 Chicago Midway to Orlando are usually found in January or February, booked 90 days in advance, depart on a Saturday or Thursday and return on a Saturday
Cheap flight deals from Midway to Orlando
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Cheapest flights from Midway to OrlandoExplore the most affordable flight options available from Midway to Orlando. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 29, 2026.
Explore the most affordable flight options available from Midway to Orlando. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 29, 2026.
This CheapOair deal was found by Cheapflights users on 9/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:21 am -
1 stop10h 00m
Wed 10/285:03 pm -
1 stop7h 44m
Deal found 9/23![Frontier logo]()
$205
This Trip.com deal was found by Cheapflights users on 9/25. 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 10/286:16 am -
1 stop10h 08m
Sat 10/3112:54 pm -
1 stop5h 53m
Deal found 9/25![Frontier logo]()
$207
This CheapOair deal was found by Cheapflights users on 9/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:53 am -
1 stop6h 31m
Sat 10/317:04 am -
1 stop11h 43m
Deal found 9/26![Frontier logo]()
$208
This FlightHub deal was found by Cheapflights users on 9/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:16 am -
1 stop10h 08m
Tue 11/39:25 am -
1 stop9h 22m
Deal found 9/27![Frontier logo]()
$209
This CheapOair deal was found by Cheapflights users on 9/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:16 am -
1 stop10h 08m
Tue 11/312:54 pm -
1 stop5h 53m
Deal found 9/28![Frontier logo]()
$210
This CheapOair deal was found by Cheapflights users on 9/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:21 am -
1 stop10h 00m
Thu 10/2212:52 pm -
1 stop5h 53m
Deal found 9/26![Frontier logo]()
$211
This Mytrip deal was found by Cheapflights users on 9/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:25 am -
1 stop13h 13m
Tue 11/105:03 pm -
1 stop7h 44m
Deal found 9/26![Frontier logo]()
$212
This Mytrip deal was found by Cheapflights users on 9/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:25 am -
1 stop13h 13m
Wed 11/412:54 pm -
1 stop5h 53m
Deal found 9/27![Frontier logo]()
$213
This Justfly.com deal was found by Cheapflights users on 9/28. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:16 am -
1 stop10h 08m
Thu 11/1212:54 pm -
1 stop5h 53m
Deal found 9/28![Frontier logo]()
$214
This Trip.com deal was found by Cheapflights users on 9/28. 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.
Sat 11/76:42 pm -
1 stop11h 19m
Sat 11/1412:54 pm -
1 stop5h 53m
Deal found 9/28![Frontier logo]()
$215
This CheapOair deal was found by Cheapflights users on 9/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:15 am -
1 stop10h 06m
Sat 10/242:52 pm -
1 stop9h 51m
Deal found 9/28![Frontier logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 9/28. 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 10/216:21 am -
1 stop10h 00m
Wed 10/285:03 pm -
1 stop7h 44m
Deal found 9/28![Frontier logo]()
$217
Best flights from Midway to OrlandoDiscover carefully curated flight deals from Midway to Orlando that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 29, 2026.
Discover carefully curated flight deals from Midway to Orlando that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 11/133:16 pm -
1 stop26h 16m
Mon 11/1611:10 am -
1 stop5h 31m
Deal found 9/23![Allegiant Air logo]()
$276
This Southwest deal was found by Cheapflights users on 9/25. 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 12/228:35 pm -
Nonstop2h 40m
Tue 1/123:10 pm -
Nonstop2h 55m
Deal found 9/25![Southwest logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 9/28. 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.
Mon 11/94:31 pm -
1 stop16h 36m
Mon 11/166:22 pm -
2 stops30h 25m
Deal found 9/28![Multiple Airlines logo]()
$379
This Southwest deal was found by Cheapflights users on 9/28. 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.
Tue 10/273:25 pm -
Nonstop2h 35m
Tue 11/34:10 pm -
Nonstop2h 55m
Deal found 9/28![Southwest logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 10/121:26 pm -
1 stop4h 51m
Thu 10/297:56 pm -
1 stop18h 40m
Deal found 9/25![Allegiant Air logo]()
$384
This Southwest deal was found by Cheapflights users on 9/28. 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.
Tue 11/173:00 pm -
Nonstop2h 40m
Thu 11/194:10 pm -
Nonstop2h 55m
Deal found 9/28![Southwest logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 9/28. 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.
Mon 11/26:42 pm -
2 stops38h 23m
Mon 11/911:10 am -
1 stop5h 31m
Deal found 9/28![Multiple Airlines logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 11/68:09 pm -
1 stop21h 23m
Mon 11/911:10 am -
1 stop5h 31m
Deal found 9/25![Allegiant Air logo]()
$391
This Southwest deal was found by Cheapflights users on 9/24. 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 10/287:55 am -
1 stop4h 15m
Wed 10/284:20 pm -
1 stop4h 20m
Deal found 9/24![Southwest logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 9/27. 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.
Mon 11/21:26 pm -
1 stop4h 51m
Sun 11/87:49 pm -
1 stop20h 52m
Deal found 9/27![Allegiant Air logo]()
$395
This Southwest deal was found by Cheapflights users on 9/24. 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.
Mon 11/237:50 am -
2 stops6h 20m
Wed 11/258:10 am -
1 stop4h 50m
Deal found 9/24![Southwest logo]()
$368
This Kiwi.com deal was found by Cheapflights users on 9/28. 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.
Fri 11/66:16 am -
2 stops29h 25m
Mon 11/911:10 am -
1 stop5h 31m
Deal found 9/28![Multiple Airlines logo]()
$456
This Southwest deal was found by Cheapflights users on 9/25. 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 10/3112:10 pm -
Nonstop2h 35m
Sun 11/19:10 am -
1 stop4h 15m
Deal found 9/25![Southwest logo]()
$374
This Kiwi.com deal was found by Cheapflights users on 9/28. 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.
Fri 11/68:09 pm -
1 stop21h 23m
Sun 11/157:49 pm -
1 stop20h 52m
Deal found 9/28![Allegiant Air logo]()
$440
This Southwest deal was found by Cheapflights users on 9/26. 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.
Sun 12/67:50 am -
2 stops6h 20m
Mon 12/143:50 pm -
1 stop4h 50m
Deal found 9/26![Southwest logo]()
$389
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 11/68:09 pm -
1 stop16h 28m
Sun 11/87:49 pm -
1 stop20h 52m
Deal found 9/25![Allegiant Air logo]()
$448
This Southwest deal was found by Cheapflights users on 9/24. 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 12/57:50 am -
2 stops5h 30m
Fri 12/113:50 pm -
1 stop5h 10m
Deal found 9/24![Southwest logo]()
$392
This Kiwi.com deal was found by Cheapflights users on 9/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/121:26 pm -
1 stop4h 51m
Thu 10/159:59 pm -
1 stop18h 41m
Deal found 9/26![Allegiant Air logo]()
$453
This Southwest deal was found by Cheapflights users on 9/27. 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 11/58:40 pm -
Nonstop2h 40m
Sun 11/87:10 am -
Nonstop3h 00m
Deal found 9/27![Southwest logo]()
$398
This Southwest deal was found by Cheapflights users on 9/26. 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 10/152:15 pm -
Nonstop2h 35m
Thu 10/292:25 pm -
Nonstop2h 50m
Deal found 9/26![Southwest logo]()
$398
This Southwest deal was found by Cheapflights users on 9/25. 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.
Fri 12/258:25 am -
1 stop4h 25m
Wed 12/308:10 am -
1 stop4h 50m
Deal found 9/25![Southwest logo]()
$403
Last-minute flights from Midway to OrlandoDiscover last-minute flight deals from Midway to Orlando. Data last updated September 29, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Orlando. Data last updated September 29, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/27. 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.
Mon 10/121:26 pm -
1 stop20h 07m
Thu 10/297:56 pm -
1 stop18h 40m
Deal found 9/27![Allegiant Air logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 9/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/121:26 pm -
1 stop4h 51m
Thu 10/159:59 pm -
1 stop18h 41m
Deal found 9/26![Allegiant Air logo]()
$453
This CheapOair deal was found by Cheapflights users on 9/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:15 am -
1 stop10h 06m
Sat 10/242:52 pm -
1 stop9h 51m
Deal found 9/28![Frontier logo]()
$216
This CheapOair deal was found by Cheapflights users on 9/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:21 am -
1 stop10h 00m
Thu 10/2212:52 pm -
1 stop5h 53m
Deal found 9/25![Frontier logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 9/28. 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 10/216:21 am -
1 stop10h 00m
Wed 10/285:03 pm -
1 stop7h 44m
Deal found 9/28![Frontier logo]()
$217
This FlightHub deal was found by Cheapflights users on 9/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:15 am -
1 stop10h 06m
Tue 10/2712:54 pm -
1 stop5h 33m
Deal found 9/28![Frontier logo]()
$214
This CheapOair deal was found by Cheapflights users on 9/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:21 am -
1 stop10h 00m
Wed 10/285:03 pm -
1 stop7h 44m
Deal found 9/23![Frontier logo]()
$205
This CheapOair deal was found by Cheapflights users on 9/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:53 am -
1 stop6h 31m
Sat 10/317:04 am -
1 stop11h 43m
Deal found 9/26![Frontier logo]()
$208
This Trip.com deal was found by Cheapflights users on 9/25. 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 10/286:16 am -
1 stop10h 08m
Sat 10/3112:54 pm -
1 stop5h 53m
Deal found 9/25![Frontier logo]()
$207
This FlightHub deal was found by Cheapflights users on 9/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:16 am -
1 stop10h 08m
Tue 11/39:25 am -
1 stop9h 22m
Deal found 9/27![Frontier logo]()
$209
This Mytrip deal was found by Cheapflights users on 9/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:25 am -
1 stop13h 13m
Tue 11/105:03 pm -
1 stop7h 44m
Deal found 9/26![Frontier logo]()
$212
This Mytrip deal was found by Cheapflights users on 9/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:25 am -
1 stop13h 13m
Wed 11/412:54 pm -
1 stop5h 53m
Deal found 9/27![Frontier logo]()
$213
One-way flights from Midway to OrlandoSearch for one-way flight options from Midway to Orlando. Find affordable one-way fares based on user searches. Data last updated September 29, 2026.
Search for one-way flight options from Midway to Orlando. Find affordable one-way fares based on user searches. Data last updated September 29, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 9/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:53 am -
1 stop6h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Frontier logo]()
$98
This Cheapflightsfares deal was found by Cheapflights users on 9/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:28 pm -
1 stop10h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Frontier logo]()
$101
This Expedia deal was found by Cheapflights users on 9/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:21 am -
1 stop10h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Frontier logo]()
$103
This CheapOair deal was found by Cheapflights users on 9/24. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:21 am -
1 stop10h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Frontier logo]()
$105
This Super.com deal was found by Cheapflights users on 9/28. 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.
Thu 10/296:16 am -
1 stop10h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Frontier logo]()
$106
This Super.com deal was found by Cheapflights users on 9/24. 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 10/286:42 pm -
1 stop11h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Frontier logo]()
$107
This Expedia deal was found by Cheapflights users on 9/25. 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.
Mon 10/196:15 am -
1 stop10h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 10/236:15 am -
1 stop24h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 9/28. 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 10/246:21 am -
1 stop12h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Frontier logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 9/28. 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.
Sun 11/16:42 pm -
1 stop14h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 11/133:16 pm -
1 stop26h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Allegiant Air logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 9/27. 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.
Mon 11/21:26 pm -
1 stop25h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Allegiant Air logo]()
$134
Find flight deals from Midway to Orlando
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Orlando (ORL). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $205 (CheapOair) |
One-way from | $98 (Cheapflightsfares) |
Popular in | June |
Cheapest in | January |
Average price | $380 |
Good round-trip deal | $364 or less |
Good one-way deal | $184 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Orlando that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 29, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Orlando that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoOrlando
MDW Chicago Midway - SFB Orlando Sanford Intl
MDWSFB
Chicago Midway
Fri 11/13
3:16 pm-6:32 pm
1 stop26h 16m
Orlando Sanford Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$119
Quickest round-trip
ChicagoOrlando
MDW Chicago Midway - MCO Orlando
MDWMCO
Chicago Midway
Tue 12/15
5:20 am-8:50 am
Nonstop2h 30m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$174
ChicagoOrlando
MDW Chicago Midway - SFB Orlando Sanford Intl
MDWSFB
Chicago Midway
Fri 11/6
8:09 pm-6:32 pm
1 stop21h 23m
Orlando Sanford Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$174
ChicagoOrlando
MDW Chicago Midway - MCO Orlando
MDWMCO
Chicago Midway
Sat 11/7
5:00 am-8:35 am
Nonstop2h 35m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$174
ChicagoOrlando
MDW Chicago Midway - SFB Orlando Sanford Intl
MDWSFB
Chicago Midway
Thu 10/29
6:16 am-11:39 pm
3 stops40h 23m
Orlando Sanford Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$177
ChicagoOrlando
MDW Chicago Midway - MCO Orlando
MDWMCO
Chicago Midway
Mon 11/2
8:40 pm-12:15 am
Nonstop2h 35m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$179
ChicagoOrlando
MDW Chicago Midway - MCO Orlando
MDWMCO
Chicago Midway
Sat 11/21
8:50 pm-12:30 am
Nonstop2h 40m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$179
ChicagoOrlando
MDW Chicago Midway - MCO Orlando
MDWMCO
Chicago Midway
Tue 10/20
4:40 pm-8:15 pm
Nonstop2h 35m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$179
ChicagoOrlando
MDW Chicago Midway - MCO Orlando
MDWMCO
Chicago Midway
Sat 10/24
9:40 am-1:25 pm
Nonstop2h 45m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$179
ChicagoOrlando
MDW Chicago Midway - MCO Orlando
MDWMCO
Chicago Midway
Thu 10/29
3:45 pm-7:20 pm
Nonstop2h 35m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$179
Showing 1-10 of 44 resultsSorted by cheapest first
Compare providers for flights from Midway to Orlando
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 Midway to Orlando in September.
| 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 Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Orlando flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Orlando flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Orlando flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Orlando 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 Chicago Midway Airport-Orlando 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 Midway to Orlando
Have a flexible travel schedule? Discover the best time to fly to Orlando from Midway with our price prediction graph.
MDW-ORL
MDW-MCO
MDW-SFB
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to Orlando
MDW-ORL
MDW-MCO
MDW-SFB
What is the cheapest month to book a flight from Chicago Midway Airport to Orlando?
Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Orlando (average of $210). Flying from Chicago Midway Airport to Orlando in June is currently the most expensive (average of $460). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MDW to ORL?
Find hourly flight availability from Midway to Orlando. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 29, 2026.
It’s typically best to fly out from Chicago Midway Airport to Orlando in the afternoon. Doing so could potentially save you 18% on the flight price compared to flying in the morning, which is usually more expensive.
How much does it cost to fly round-trip from Chicago Midway Airport to Orlando?
Airfare is typical for this route at the moment.
Chicago Midway Airport to Orlando flights typically cost between $170 and $329 in October.The cheapest round-trip price found within the last 5 days was $205 on Frontier (Oct 24-Oct 28).
How often are flights from Chicago to Orlando delayed?
About 17% of weekly flights between Chicago and Orlando have experienced delays in the past year, with the average delay time being 135 minutes.
What is the most punctual flight time for Chicago to Orlando flights?
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening 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 Chicago to Orlando flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 17% of flights being delayed.
How far ahead should I book a flight from Chicago Midway Airport to Orlando?
To ensure you get the cheapest price possible for a flight from Chicago Midway Airport to Orlando, you should look to book at least 89 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Chicago Midway Airport to Orlando?
Use this chart to determine the cheapest time to fly round-trip from Midway to Orlando. Price data was last updated on September 26, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Orlando flight should consider departing on Monday at noon when fares are most often at their lowest. Wednesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Chicago Midway Airport to Orlando 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 Chicago Midway Airport to Orlando trip
Our travel experts
Reviews of airlines servicing Orlando
Get insights into the airlines that provide service to Orlando. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Orlando. Reviews last updated September 29, 2026.
Read reviews from past customers who have flown Southwest and Frontier from Chicago Midway Airport to Orlando. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Midway to Orlando. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Other flights to Orlando
Explore flights to Orlando departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 29, 2026.
Midway and Orlando flights
Browse other Midway and Orlando flight options. Last updated on September 29, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on September 29, 2026.
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Top 2 airlines flying from Midway to Orlando
Discover the top 2 airlines that operate flights from Midway to Orlando. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$65 | Average$207 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$216 | Average$427 | FlexibilityNo cancel fee | On-time63% |