$94+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Jul 16 — Jul 231
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 August or January, booked 90 days in advance, depart on a Thursday or Sunday and return on a Friday
Cheap flight deals from Midway to Walt Disney World
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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 June 16, 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 June 16, 2026.
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:20 pm
MDW
- MCO
Nonstop2h 40m
Southwest
Wed 8/267:15 pm
MCO
- MDW
Nonstop2h 45m
Southwest
Deal found 6/11![Southwest logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 6/11. 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 8/56:05 am
MDW
- MCO
1 stop11h 28m
Frontier
Tue 8/115:24 pm
MCO
- MDW
1 stop5h 39m
Frontier
Deal found 6/11![Frontier logo]()
$195
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:20 pm
MDW
- MCO
Nonstop2h 40m
Southwest
Tue 8/119:00 am
MCO
- MDW
1 stop4h 05m
Southwest
Deal found 6/11![Southwest logo]()
$196
This Southwest deal was found by Cheapflights users on 6/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/88:10 pm
MDW
- MCO
Nonstop2h 40m
Southwest
Tue 7/146:10 pm
MCO
- MDW
Nonstop3h 00m
Southwest
Deal found 6/12![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:15 am
MDW
- MCO
Nonstop2h 30m
Southwest
Sat 10/38:50 am
MCO
- MDW
1 stop5h 20m
Southwest
Deal found 6/11![Southwest logo]()
$216
This Trip.com deal was found by Cheapflights users on 6/13. 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.
Wed 8/1211:06 am
MDW
- MCO
1 stop6h 27m
Frontier
Tue 8/185:31 am
MCO
- MDW
1 stop6h 41m
Frontier
Deal found 6/13![Frontier logo]()
$217
This Frontier deal was found by Cheapflights users on 6/11. 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.
Wed 7/294:45 pm
MDW
- MCO
1 stop6h 14m
Frontier
Tue 8/45:20 am
MCO
- MDW
1 stop6h 47m
Frontier
Deal found 6/11![Frontier logo]()
$220
This Gotogate deal was found by Cheapflights users on 6/14. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/294:45 pm
MDW
- MCO
1 stop6h 14m
Frontier
Wed 8/55:40 am
MCO
- MDW
1 stop11h 10m
Frontier
Deal found 6/14![Frontier logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Fri 7/243:28 pm
MDW
- SFB
1 stop7h 07m
Allegiant Air
Sun 7/268:58 pm
SFB
- MDW
1 stop18h 40m
Allegiant Air
Deal found 6/11![Allegiant Air logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 6/14. 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.
Sun 7/122:48 pm
MDW
- SFB
1 stop4h 41m
Allegiant Air
Sun 7/198:58 pm
SFB
- MDW
1 stop18h 40m
Allegiant Air
Deal found 6/14![Allegiant Air logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 6/14. 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.
Fri 7/33:28 pm
MDW
- SFB
1 stop7h 07m
Allegiant Air
Sun 7/128:58 pm
SFB
- MDW
1 stop18h 40m
Allegiant Air
Deal found 6/14![Allegiant Air logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 6/14. 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.
Thu 7/92:48 pm
MDW
- SFB
1 stop25h 33m
Allegiant Air
Wed 7/224:48 pm
SFB
- MDW
1 stop22h 10m
Allegiant Air
Deal found 6/14![Allegiant Air logo]()
$264
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 June 16, 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 June 16, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/14. 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.
Sun 7/122:48 pm
MDW
- SFB
1 stop4h 41m
Allegiant Air
Sun 7/198:58 pm
SFB
- MDW
1 stop18h 40m
Allegiant Air
Deal found 6/14![Allegiant Air logo]()
$249
This Southwest deal was found by Cheapflights users on 6/13. 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.
Wed 9/93:30 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Sat 9/127:05 am
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 6/13![Southwest logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 6/12. 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.
Wed 8/511:06 am
MDW
- SFB
2 stops32h 28m
Multiple Airlines
Sun 8/99:20 pm
SFB
- MDW
1 stop18h 39m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$333
This Southwest deal was found by Cheapflights users on 6/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/58:30 am
MDW
- MCO
Nonstop2h 45m
Southwest
Sat 8/86:15 am
MCO
- MDW
1 stop5h 25m
Southwest
Deal found 6/12![Southwest logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 6/14. 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.
Thu 7/92:48 pm
MDW
- SFB
1 stop25h 33m
Allegiant Air
Wed 7/224:48 pm
SFB
- MDW
1 stop22h 10m
Allegiant Air
Deal found 6/14![Allegiant Air logo]()
$264
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/110:15 am
MDW
- MCO
1 stop4h 05m
Southwest
Wed 8/57:15 pm
MCO
- MDW
Nonstop2h 45m
Southwest
Deal found 6/15![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 6/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/11:25 pm
MDW
- MCO
1 stop5h 40m
Southwest
Wed 7/298:00 am
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 6/14![Southwest logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 6/14. 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.
Fri 7/33:28 pm
MDW
- SFB
1 stop7h 07m
Allegiant Air
Sun 7/58:58 pm
SFB
- MDW
1 stop18h 40m
Allegiant Air
Deal found 6/14![Allegiant Air logo]()
$316
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/155:30 pm
MDW
- MCO
Nonstop2h 50m
Southwest
Mon 7/207:25 am
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 6/15![Southwest logo]()
$288
This Kiwi.com deal was found by Cheapflights users on 6/13. 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 7/2112:11 pm
MDW
- SFB
2 stops29h 39m
Multiple Airlines
Sat 7/258:24 pm
SFB
- MDW
1 stop18h 34m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 6/13. 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.
Fri 6/266:38 pm
MDW
- SFB
1 stop18h 15m
Allegiant Air
Sun 6/288:58 pm
SFB
- MDW
1 stop21h 50m
Allegiant Air
Deal found 6/13![Allegiant Air logo]()
$354
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/276:35 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Tue 7/284:40 pm
MCO
- MDW
1 stop4h 10m
Southwest
Deal found 6/15![Southwest logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 6/14. 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.
Thu 7/232:48 pm
MDW
- SFB
1 stop25h 33m
Multiple Airlines
Fri 7/316:02 pm
SFB
- MDW
2 stops29h 01m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$432
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2512:50 pm
MDW
- MCO
1 stop4h 10m
Southwest
Sat 8/17:00 am
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 6/15![Southwest logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/63:28 pm
MDW
- SFB
1 stop26h 56m
Allegiant Air
Sat 7/118:19 pm
SFB
- MDW
1 stop18h 39m
Allegiant Air
Deal found 6/15![Allegiant Air logo]()
$370
This Southwest deal was found by Cheapflights users on 6/13. 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 8/67:50 pm
MDW
- MCO
Nonstop2h 30m
Southwest
Mon 8/107:45 pm
MCO
- MDW
Nonstop2h 45m
Southwest
Deal found 6/13![Southwest logo]()
$304
This Southwest deal was found by Cheapflights users on 6/13. 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.
Fri 8/285:00 am
MDW
- MCO
Nonstop2h 30m
Southwest
Mon 8/3110:00 am
MCO
- MDW
Nonstop2h 45m
Southwest
Deal found 6/13![Southwest logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/302:48 pm
MDW
- SFB
1 stop25h 33m
Allegiant Air
Mon 8/36:30 am
SFB
- MDW
2 stops15h 00m
Allegiant Air
Deal found 6/15![Allegiant Air logo]()
$443
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/257:35 pm
MDW
- MCO
Nonstop2h 40m
Southwest
Mon 7/276:50 am
MCO
- MDW
1 stop4h 10m
Southwest
Deal found 6/11![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/28:20 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Fri 8/76:55 am
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 6/11![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 6/13. 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.
Sat 8/15:05 pm
MDW
- MCO
Nonstop2h 50m
Southwest
Sun 8/27:15 am
MCO
- MDW
1 stop4h 50m
Southwest
Deal found 6/13![Southwest logo]()
$324
Last-minute flights from Midway to Walt Disney WorldDiscover last-minute flight deals from Midway to Walt Disney World. Data last updated June 16, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Walt Disney World. Data last updated June 16, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/14. 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.
Fri 7/33:28 pm
MDW
- SFB
1 stop7h 07m
Allegiant Air
Sun 7/128:58 pm
SFB
- MDW
1 stop18h 40m
Allegiant Air
Deal found 6/14![Allegiant Air logo]()
$255
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/88:10 pm
MDW
- MCO
Nonstop2h 40m
Southwest
Tue 7/146:10 pm
MCO
- MDW
Nonstop3h 00m
Southwest
Deal found 6/11![Southwest logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 6/12. 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 7/103:28 pm
MDW
- MCO
1 stop17h 41m
Allegiant Air
Mon 7/1310:59 am
MCO
- MDW
1 stop4h 39m
Allegiant Air
Deal found 6/12![Allegiant Air logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 6/14. 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.
Sun 7/122:48 pm
MDW
- SFB
1 stop4h 41m
Allegiant Air
Sun 7/198:58 pm
SFB
- MDW
1 stop18h 40m
Allegiant Air
Deal found 6/14![Allegiant Air logo]()
$249
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/149:19 am
MDW
- MCO
1 stop4h 40m
Delta
Tue 7/213:40 pm
MCO
- MDW
1 stop7h 35m
Delta
Deal found 6/11![Delta logo]()
$229
This Expedia deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1412:11 pm
MDW
- MCO
1 stop9h 04m
Frontier
Tue 7/215:24 pm
MCO
- MDW
1 stop5h 39m
Frontier
Deal found 6/15![Frontier logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2212:11 pm
MDW
- MCO
1 stop5h 22m
Frontier
Tue 7/285:24 pm
MCO
- MDW
1 stop5h 39m
Frontier
Deal found 6/15![Frontier logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Fri 7/243:28 pm
MDW
- SFB
1 stop7h 07m
Allegiant Air
Sun 7/268:58 pm
SFB
- MDW
1 stop18h 40m
Allegiant Air
Deal found 6/11![Allegiant Air logo]()
$226
This Frontier deal was found by Cheapflights users on 6/14. 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.
Sat 7/2512:11 pm
MDW
- MCO
1 stop9h 04m
Frontier
Tue 8/45:20 am
MCO
- MDW
1 stop6h 47m
Frontier
Deal found 6/14![Frontier logo]()
$234
This Frontier deal was found by Cheapflights users on 6/13. 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 7/2812:11 pm
MDW
- MCO
1 stop9h 04m
Frontier
Tue 8/45:40 am
MCO
- MDW
1 stop12h 11m
Frontier
Deal found 6/13![Frontier logo]()
$222
This Frontier deal was found by Cheapflights users on 6/11. 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.
Wed 7/294:45 pm
MDW
- MCO
1 stop6h 14m
Frontier
Tue 8/45:20 am
MCO
- MDW
1 stop6h 47m
Frontier
Deal found 6/11![Frontier logo]()
$220
This Frontier deal was found by Cheapflights users on 6/14. 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.
Wed 7/294:45 pm
MDW
- MCO
1 stop6h 14m
Frontier
Wed 8/55:40 am
MCO
- MDW
1 stop11h 10m
Frontier
Deal found 6/14![Frontier logo]()
$221
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 June 16, 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 June 16, 2026.
This Trip.com deal was found by Cheapflights users on 6/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1211:06 am
MDW
- MCO
1 stop10h 09m
Frontier
Deal found 6/11![Frontier logo]()
$94
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:20 pm
MDW
- MCO
Nonstop2h 40m
Southwest
Deal found 6/11![Southwest logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Tue 9/86:00 am
MDW
- MCO
1 stop15h 09m
Frontier
Deal found 6/11![Frontier logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Tue 8/1111:06 am
MDW
- MCO
1 stop18h 34m
Frontier
Deal found 6/11![Frontier logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Tue 8/412:11 pm
MDW
- MCO
1 stop9h 04m
Frontier
Deal found 6/11![Frontier logo]()
$101
This Trip.com deal was found by Cheapflights users on 6/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1512:11 pm
MDW
- MCO
1 stop9h 04m
Frontier
Deal found 6/11![Frontier logo]()
$104
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:05 am
MDW
- MCO
1 stop7h 27m
Delta
Deal found 6/12![Delta logo]()
$106
This Trip.com deal was found by Cheapflights users on 6/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:05 am
MDW
- MCO
1 stop12h 52m
Frontier
Deal found 6/11![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Fri 7/243:28 pm
MDW
- SFB
1 stop7h 07m
Allegiant Air
Deal found 6/11![Allegiant Air logo]()
$110
This Southwest deal was found by Cheapflights users on 6/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/143:00 pm
MDW
- MCO
1 stop3h 55m
Southwest
Deal found 6/12![Southwest logo]()
$110
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:40 am
MDW
- MCO
2 stops5h 55m
Southwest
Deal found 6/11![Southwest logo]()
$111
This Frontier deal was found by Cheapflights users on 6/13. 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.
Wed 9/212:04 pm
MDW
- MCO
1 stop9h 05m
Frontier
Deal found 6/13![Frontier logo]()
$112
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 June 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $191 (Southwest) |
One-way from | $94 (Trip.com) |
Popular in | March |
Cheapest in | August |
Average price | $332 |
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 June 16, 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
Sun 7/12
2:48 pm-8:29 pm
1 stop4h 41m
Orlando Sanford Intl
Sun 7/19
8:58 pm-2:38 pm
1 stop18h 40m
$249
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Wed 9/9
3:30 pm-7:05 pm
Nonstop2h 35m
Orlando
Sat 9/12
7:05 am-8:55 am
Nonstop2h 50m
$253
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Wed 8/5
8:30 am-12:15 pm
Nonstop2h 45m
Orlando
Sat 8/8
6:15 am-10:40 am
1 stop5h 25m
$263
ChicagoOrlando
MDW - SFB
MDWSFB
Chicago Midway
Thu 7/9
2:48 pm-5:21 pm
1 stop25h 33m
Orlando Sanford Intl
Wed 7/22
4:48 pm-1:58 pm
1 stop22h 10m
$264
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Sat 8/1
10:15 am-3:20 pm
1 stop4h 05m
Orlando
Wed 8/5
7:15 pm-9:00 pm
Nonstop2h 45m
$273
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Wed 7/1
1:25 pm-8:05 pm
1 stop5h 40m
Orlando
Wed 7/29
8:00 am-9:50 am
Nonstop2h 50m
$277
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Wed 7/15
5:30 pm-9:20 pm
Nonstop2h 50m
Orlando
Mon 7/20
7:25 am-9:15 am
Nonstop2h 50m
$288
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Mon 7/27
6:35 pm-10:10 pm
Nonstop2h 35m
Orlando
Tue 7/28
4:40 pm-7:50 pm
1 stop4h 10m
$294
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Sat 7/25
12:50 pm-6:00 pm
1 stop4h 10m
Orlando
Sat 8/1
7:00 am-8:50 am
Nonstop2h 50m
$303
Quickest round-trip
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Thu 8/6
7:50 pm-11:20 pm
Nonstop2h 30m
Orlando
Mon 8/10
7:45 pm-9:30 pm
Nonstop2h 45m
$304
Showing 1-10 of 38 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 June 16, 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 20% on your trip compared to booking a flight at noon.
Weekly flight availability from Chicago Midway Airport to Walt Disney World
Explore weekly flight availability from Midway to Walt Disney World. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 16, 2026.
The most flights from MDW to W9D are scheduled on a Saturday (14 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Chicago Midway Airport to Walt Disney World?
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 June 13, 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. Tuesday at noon 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 June 16, 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.
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Boarding
8.1
Entertainment
7.5
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 June 16, 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 June 16, 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 June 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$70 | Average$176 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$174 | Average$369 | FlexibilityNo cancel fee | On-time63% |