$100+ Cheap flights from Midway (MDW) to Bay Lake, FL
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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
août 23 — août 301
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Walt Disney World 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 Walt Disney World are usually found in January or February, booked 90 days in advance, depart on a Sunday or Thursday and return on a Friday
Cheap flight deals from Midway to Walt Disney World
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Best
Last-minute
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Cheapest flights from Midway to Walt Disney WorldExplore the most affordable flight options available from Midway to Walt Disney World. Find the lowest fares from popular airlines and budget airlines, with prices last updated on juillet 24, 2026.
Explore the most affordable flight options available from Midway to Walt Disney World. Find the lowest fares from popular airlines and budget airlines, with prices last updated on juillet 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
sam. 11/712:03 pm
MDW
- MCO
1 stop9h 07m
Frontier
jeu. 11/125:29 pm
MCO
- MDW
1 stop5h 24m
Frontier
Deal found 7/20![Frontier logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
mer. 10/2112:03 pm
MDW
- MCO
1 stop9h 07m
Frontier
mar. 10/275:29 pm
MCO
- MDW
1 stop5h 24m
Frontier
Deal found 7/20![Frontier logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 7/19. 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.
sam. 10/2412:03 pm
MDW
- MCO
1 stop9h 07m
Frontier
mar. 10/275:29 pm
MCO
- MDW
1 stop5h 24m
Frontier
Deal found 7/19![Frontier logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
sam. 9/511:45 am
MDW
- MCO
1 stop7h 15m
Frontier
sam. 9/125:29 pm
MCO
- MDW
1 stop5h 29m
Frontier
Deal found 7/22![Frontier logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
lun. 8/2411:50 am
MDW
- MCO
1 stop7h 10m
Frontier
jeu. 8/275:23 pm
MCO
- MDW
1 stop6h 24m
Frontier
Deal found 7/23![Frontier logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
sam. 8/156:05 am
MDW
- MCO
1 stop7h 18m
Frontier
mar. 8/185:23 pm
MCO
- MDW
1 stop6h 24m
Frontier
Deal found 7/22![Frontier logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
mer. 8/1211:06 am
MDW
- MCO
1 stop6h 27m
Multiple Airlines
lun. 8/1710:29 am
MCO
- MDW
1 stop5h 30m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
jeu. 8/2011:50 am
MDW
- MCO
1 stop7h 10m
Frontier
lun. 8/243:21 pm
MCO
- MDW
1 stop8h 26m
Frontier
Deal found 7/23![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
mer. 9/97:25 am
MDW
- MCO
1 stop8h 56m
Frontier
lun. 9/145:29 pm
MCO
- MDW
1 stop5h 29m
Frontier
Deal found 7/22![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
sam. 9/267:25 am
MDW
- MCO
1 stop8h 56m
Frontier
lun. 9/285:29 pm
MCO
- MDW
1 stop5h 29m
Frontier
Deal found 7/22![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
sam. 8/1511:06 am
MDW
- MCO
1 stop7h 51m
Frontier
lun. 8/173:18 pm
MCO
- MDW
1 stop7h 45m
Frontier
Deal found 7/22![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
jeu. 8/132:49 pm
MDW
- SFB
1 stop23h 22m
Allegiant Air
dim. 8/169:20 pm
SFB
- MDW
1 stop18h 39m
Allegiant Air
Deal found 7/22![Allegiant Air logo]()
$218
Best flights from Midway to Walt Disney WorldDiscover carefully curated flight deals from Midway to Walt Disney World that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated juillet 24, 2026.
Discover carefully curated flight deals from Midway to Walt Disney World that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated juillet 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
jeu. 8/132:49 pm
MDW
- SFB
1 stop23h 22m
Allegiant Air
dim. 8/169:20 pm
SFB
- MDW
1 stop18h 39m
Allegiant Air
Deal found 7/22![Allegiant Air logo]()
$218
This Southwest deal was found by Cheapflights users on 7/22. 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.
mer. 9/96:20 pm
MDW
- MCO
Nonstop2h 40m
Southwest
jeu. 9/108:15 am
MCO
- MDW
Nonstop2h 45m
Southwest
Deal found 7/22![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 7/20. 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.
mar. 9/89:29 am
MDW
- MCO
1 stop6h 53m
Delta
ven. 9/116:40 pm
MCO
- MDW
1 stop5h 04m
Delta
Deal found 7/20![Delta logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
ven. 8/143:49 pm
MDW
- SFB
1 stop21h 11m
Multiple Airlines
dim. 8/166:35 am
SFB
- MDW
2 stops16h 28m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 7/21. 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.
dim. 8/92:49 pm
MDW
- SFB
1 stop23h 22m
Allegiant Air
dim. 8/169:20 pm
SFB
- MDW
1 stop18h 39m
Allegiant Air
Deal found 7/21![Allegiant Air logo]()
$236
This Southwest deal was found by Cheapflights users on 7/24. 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.
mar. 9/226:20 pm
MDW
- MCO
Nonstop2h 45m
Southwest
jeu. 9/248:55 pm
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 7/24![Southwest logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
ven. 8/143:49 pm
MDW
- SFB
1 stop21h 11m
Allegiant Air
dim. 8/169:20 pm
SFB
- MDW
1 stop18h 39m
Allegiant Air
Deal found 7/20![Allegiant Air logo]()
$238
This Southwest deal was found by Cheapflights users on 7/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 8/2011:15 am
MDW
- MCO
Nonstop2h 35m
Southwest
lun. 8/247:10 am
MCO
- MDW
1 stop5h 15m
Southwest
Deal found 7/23![Southwest logo]()
$243
This Southwest deal was found by Cheapflights users on 7/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 8/196:20 pm
MDW
- MCO
Nonstop2h 40m
Southwest
mer. 8/263:05 pm
MCO
- MDW
1 stop5h 25m
Southwest
Deal found 7/23![Southwest logo]()
$243
This Delta deal was found by Cheapflights users on 7/20. 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.
sam. 8/1510:56 am
MDW
- MCO
1 stop6h 55m
Delta
sam. 8/224:45 pm
MCO
- MDW
1 stop6h 51m
Delta
Deal found 7/20![Delta logo]()
$324
This Southwest deal was found by Cheapflights users on 7/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 8/157:50 am
MDW
- MCO
1 stop4h 05m
Southwest
mar. 8/189:00 am
MCO
- MDW
1 stop4h 05m
Southwest
Deal found 7/23![Southwest logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
ven. 7/313:28 pm
MDW
- SFB
1 stop7h 07m
Allegiant Air
dim. 8/28:58 pm
SFB
- MDW
1 stop18h 40m
Allegiant Air
Deal found 7/23![Allegiant Air logo]()
$317
This Southwest deal was found by Cheapflights users on 7/19. 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.
jeu. 8/272:55 pm
MDW
- MCO
Nonstop2h 35m
Southwest
lun. 8/318:55 pm
MCO
- MDW
Nonstop2h 45m
Southwest
Deal found 7/19![Southwest logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
lun. 8/33:28 pm
MDW
- SFB
1 stop7h 07m
Allegiant Air
dim. 8/99:20 pm
SFB
- MDW
1 stop18h 39m
Allegiant Air
Deal found 7/23![Allegiant Air logo]()
$330
This Southwest deal was found by Cheapflights users on 7/20. 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.
lun. 8/315:00 am
MDW
- MCO
Nonstop2h 30m
Southwest
mar. 9/159:00 am
MCO
- MDW
1 stop5h 10m
Southwest
Deal found 7/20![Southwest logo]()
$275
This Southwest deal was found by Cheapflights users on 7/20. 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.
sam. 8/227:50 am
MDW
- MCO
1 stop4h 05m
Southwest
dim. 8/238:00 am
MCO
- MDW
Nonstop2h 45m
Southwest
Deal found 7/20![Southwest logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 7/21. 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.
dim. 8/22:48 pm
MDW
- SFB
2 stops24h 53m
Allegiant Air
dim. 8/99:20 pm
SFB
- MDW
1 stop18h 39m
Allegiant Air
Deal found 7/21![Allegiant Air logo]()
$364
This Southwest deal was found by Cheapflights users on 7/22. 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.
mer. 8/197:40 am
MDW
- MCO
2 stops5h 55m
Southwest
dim. 8/238:35 am
MCO
- MDW
1 stop5h 10m
Southwest
Deal found 7/22![Southwest logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
ven. 8/73:49 pm
MDW
- SFB
1 stop21h 11m
Allegiant Air
mer. 8/124:50 pm
SFB
- MDW
1 stop22h 09m
Allegiant Air
Deal found 7/23![Allegiant Air logo]()
$387
This Southwest deal was found by Cheapflights users on 7/20. 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.
ven. 9/47:50 pm
MDW
- MCO
Nonstop2h 30m
Southwest
lun. 9/77:10 am
MCO
- MDW
1 stop5h 15m
Southwest
Deal found 7/20![Southwest logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 7/19. 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.
jeu. 8/62:49 pm
MDW
- SFB
1 stop23h 22m
Allegiant Air
dim. 8/99:20 pm
SFB
- MDW
1 stop18h 39m
Allegiant Air
Deal found 7/19![Allegiant Air logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
jeu. 8/62:49 pm
MDW
- SFB
1 stop23h 22m
Allegiant Air
mer. 8/124:50 pm
SFB
- MDW
1 stop22h 09m
Allegiant Air
Deal found 7/23![Allegiant Air logo]()
$423
This Kiwi.com deal was found by Cheapflights users on 7/21. 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.
dim. 8/22:48 pm
MDW
- SFB
2 stops24h 53m
Allegiant Air
jeu. 8/69:20 pm
SFB
- MDW
1 stop18h 39m
Allegiant Air
Deal found 7/21![Allegiant Air logo]()
$459
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
lun. 8/33:28 pm
MDW
- SFB
1 stop7h 07m
Allegiant Air
jeu. 8/69:20 pm
SFB
- MDW
1 stop18h 39m
Allegiant Air
Deal found 7/23![Allegiant Air logo]()
$463
Last-minute flights from Midway to Walt Disney WorldDiscover last-minute flight deals from Midway to Walt Disney World. Data last updated juillet 24, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Walt Disney World. Data last updated juillet 24, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/21. 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.
dim. 8/92:49 pm
MDW
- SFB
1 stop23h 22m
Allegiant Air
dim. 8/169:20 pm
SFB
- MDW
1 stop18h 39m
Allegiant Air
Deal found 7/21![Allegiant Air logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
mar. 8/1111:06 am
MDW
- MCO
1 stop10h 09m
Frontier
sam. 8/155:24 pm
MCO
- MDW
1 stop5h 39m
Frontier
Deal found 7/22![Frontier logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
mer. 8/1211:06 am
MDW
- MCO
1 stop6h 27m
Multiple Airlines
lun. 8/1710:29 am
MCO
- MDW
1 stop5h 30m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
mer. 8/1211:06 am
MDW
- MCO
1 stop6h 27m
Frontier
mer. 8/195:23 pm
MCO
- MDW
1 stop6h 24m
Frontier
Deal found 7/22![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
jeu. 8/132:49 pm
MDW
- SFB
1 stop23h 22m
Allegiant Air
dim. 8/169:20 pm
SFB
- MDW
1 stop18h 39m
Allegiant Air
Deal found 7/22![Allegiant Air logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
ven. 8/143:49 pm
MDW
- SFB
1 stop21h 11m
Allegiant Air
dim. 8/169:20 pm
SFB
- MDW
1 stop18h 39m
Allegiant Air
Deal found 7/23![Allegiant Air logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
sam. 8/156:05 am
MDW
- MCO
1 stop7h 18m
Frontier
mar. 8/185:23 pm
MCO
- MDW
1 stop6h 24m
Frontier
Deal found 7/22![Frontier logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
sam. 8/1511:06 am
MDW
- MCO
1 stop7h 51m
Frontier
lun. 8/173:18 pm
MCO
- MDW
1 stop7h 45m
Frontier
Deal found 7/22![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
sam. 8/1511:06 am
MDW
- MCO
1 stop7h 51m
Frontier
lun. 8/243:21 pm
MCO
- MDW
1 stop8h 26m
Frontier
Deal found 7/22![Frontier logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
lun. 8/173:49 pm
MDW
- SFB
1 stop19h 08m
Multiple Airlines
sam. 8/228:30 am
SFB
- MDW
2 stops15h 17m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
jeu. 8/2011:50 am
MDW
- MCO
1 stop7h 10m
Frontier
lun. 8/243:21 pm
MCO
- MDW
1 stop8h 26m
Frontier
Deal found 7/23![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
lun. 8/2411:50 am
MDW
- MCO
1 stop7h 10m
Frontier
jeu. 8/275:23 pm
MCO
- MDW
1 stop6h 24m
Frontier
Deal found 7/23![Frontier logo]()
$207
One-way flights from Midway to Walt Disney WorldSearch for one-way flight options from Midway to Walt Disney World. Find affordable one-way fares based on user searches. Data last updated juillet 24, 2026.
Search for one-way flight options from Midway to Walt Disney World. Find affordable one-way fares based on user searches. Data last updated juillet 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
jeu. 8/132:49 pm
MDW
- MCO
1 stop28h 18m
Allegiant Air
Deal found 7/22![Allegiant Air logo]()
$100
This Trip.com deal was found by Cheapflights users on 7/22. 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.
mer. 8/1211:06 am
MDW
- MCO
1 stop6h 27m
Frontier
Deal found 7/22![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
mar. 8/256:05 am
MDW
- MCO
1 stop11h 28m
Frontier
Deal found 7/22![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
sam. 8/226:05 am
MDW
- MCO
1 stop12h 55m
Frontier
Deal found 7/22![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
mer. 8/1911:50 am
MDW
- MCO
1 stop9h 24m
Frontier
Deal found 7/22![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
jeu. 8/2011:50 am
MDW
- MCO
1 stop9h 24m
Frontier
Deal found 7/22![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
jeu. 9/2412:03 pm
MDW
- MCO
1 stop9h 07m
Frontier
Deal found 7/23![Frontier logo]()
$111
This Trip.com deal was found by Cheapflights users on 7/23. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 8/136:05 am
MDW
- MCO
1 stop7h 18m
Frontier
Deal found 7/23![Frontier logo]()
$115
This Trip.com deal was found by Cheapflights users on 7/19. 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.
dim. 8/166:05 am
MDW
- MCO
1 stop12h 52m
Frontier
Deal found 7/19![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
ven. 8/143:49 pm
MDW
- SFB
1 stop21h 11m
Allegiant Air
Deal found 7/22![Allegiant Air logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
ven. 9/1112:03 pm
MDW
- MCO
1 stop9h 07m
Frontier
Deal found 7/20![Frontier logo]()
$118
This Southwest deal was found by Cheapflights users on 7/22. 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.
lun. 8/175:00 am
MDW
- MCO
Nonstop2h 30m
Southwest
Deal found 7/22![Southwest logo]()
$119
Find flight deals from Midway to Walt Disney World
Keep the following information in mind while searching for Midway to Walt Disney World flight deals. Data was last updated juillet 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $196 (Kiwi.com) |
One-way from | $100 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $437 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Walt Disney World 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 juillet 24, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Bay Lake that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoOrlando
MDW - SFB
MDWSFB
Chicago Midway
jeu. 8/13
2:49 pm-3:11 pm
1 stop23h 22m
Orlando Sanford Intl
dim. 8/16
9:20 pm-2:59 pm
1 stop18h 39m
$218
ChicagoOrlando
MDW - SFB
MDWSFB
Chicago Midway
dim. 8/9
2:49 pm-3:11 pm
1 stop23h 22m
Orlando Sanford Intl
dim. 8/16
9:20 pm-2:59 pm
1 stop18h 39m
$236
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
mer. 9/9
6:20 pm-10:00 pm
Nonstop2h 40m
Orlando
jeu. 9/10
8:15 am-10:00 am
Nonstop2h 45m
$237
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
mar. 9/22
6:20 pm-10:05 pm
Nonstop2h 45m
Orlando
jeu. 9/24
8:55 pm-10:45 pm
Nonstop2h 50m
$237
ChicagoOrlando
MDW - SFB
MDWSFB
Chicago Midway
ven. 8/14
3:49 pm-2:00 pm
1 stop21h 11m
Orlando Sanford Intl
dim. 8/16
9:20 pm-2:59 pm
1 stop18h 39m
$238
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
jeu. 8/20
11:15 am-2:50 pm
Nonstop2h 35m
Orlando
lun. 8/24
7:10 am-11:25 am
1 stop5h 15m
$243
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
mer. 8/19
6:20 pm-10:00 pm
Nonstop2h 40m
Orlando
mer. 8/26
3:05 pm-7:30 pm
1 stop5h 25m
$243
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
sam. 8/15
7:50 am-12:55 pm
1 stop4h 05m
Orlando
mar. 8/18
9:00 am-12:05 pm
1 stop4h 05m
$248
Quickest round-trip
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
jeu. 8/27
2:55 pm-6:30 pm
Nonstop2h 35m
Orlando
lun. 8/31
8:55 pm-10:40 pm
Nonstop2h 45m
$269
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
mar. 9/8
9:29 am-5:22 pm
1 stop6h 53m
Orlando
ven. 9/11
6:40 pm-10:44 pm
1 stop5h 04m
$273
Showing 1-10 of 45 resultsSorted by cheapest first
Best time to book a flight from Midway to Walt Disney World
Have a flexible travel schedule? Discover the best time to fly to Walt Disney World from Midway with our price prediction graph.
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 Bay Lake
MDW-W9D
MDW-MCO
MDW-SFB
What is the cheapest time of day to fly from MDW to W9D?
Find hourly flight availability from Midway to Walt Disney World. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated juillet 24, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago Midway Airport to Walt Disney World in the afternoon. If you’re flexible enough to do this you can expect to save up to 16% on your trip compared to booking a flight at noon.
How much does it cost to fly round-trip from Chicago Midway Airport to Walt Disney World?
Airfare is below average for this route at the moment.
Chicago Midway Airport to Walt Disney World flights typically cost between $216 and $433 in October.The cheapest round-trip price found within the last 5 days was $196 on Frontier (Oct 21-Oct 27).
What is the cheapest day to fly from Chicago Midway Airport to Walt Disney World?
Use this chart to determine the cheapest time to fly round-trip from Midway to Walt Disney World. Price data was last updated on July 18, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Walt Disney World flight should consider departing on Monday at noon when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Walt Disney World
Get insights into the airlines that provide service to Walt Disney World. 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 Walt Disney World. Reviews last updated juillet 24, 2026.
Read reviews from past customers who have flown Southwest and Frontier from Chicago Midway Airport to Bay Lake. 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.
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
Find useful and relevant information for your journey from Midway to Walt Disney World. 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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Alternative routes for Midway to Walt Disney World
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Walt Disney World by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Walt Disney World by cabin class
Find flights from Midway to Walt Disney World, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Walt Disney World flights
Browse other Midway and Walt Disney World flight options. Last updated on juillet 24, 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 juillet 24, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Midway to Walt Disney World flights
Consider these flights traveling from Midway to Walt Disney World.
Top 2 airlines flying from Midway to Walt Disney World
Discover the top 2 airlines that operate flights from Midway to Walt Disney World. 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 juillet 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$66 | Average$180 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$181 | Average$384 | FlexibilityNo cancel fee | On-time63% |