$59+ 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 4/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
May 9 — May 161
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 September or August, booked 50 days in advance, depart on a Thursday or Friday 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 April 9, 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 April 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:15 am
MDW
- MCO
1 stop8h 14m
Multiple Airlines
Wed 4/292:40 pm
MCO
- MDW
1 stop8h 34m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$132
This Frontier deal was found by Cheapflights users on 4/8. 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.
Mon 4/135:30 am
MDW
- MCO
Nonstop2h 46m
Frontier
Fri 4/176:00 am
MCO
- MDW
Nonstop2h 59m
Frontier
Deal found 4/8![Frontier logo]()
$133
This Expedia deal was found by Cheapflights users on 4/8. 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.
Fri 5/84:52 pm
MDW
- MCO
Nonstop2h 47m
Frontier
Tue 5/123:10 pm
MCO
- MDW
1 stop7h 52m
Frontier
Deal found 4/8![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 4/212:15 pm
MDW
- MCO
1 stop19h 09m
Multiple Airlines
Fri 4/2411:18 am
MCO
- MDW
1 stop9h 13m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 4/257:34 pm
MDW
- MCO
1 stop11h 05m
Frontier
Wed 4/292:40 pm
MCO
- MDW
1 stop5h 51m
Frontier
Deal found 4/5![Frontier logo]()
$136
This Expedia deal was found by Cheapflights users on 4/6. 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.
Fri 5/154:52 pm
MDW
- MCO
Nonstop2h 47m
Frontier
Mon 5/181:57 pm
MCO
- MDW
Nonstop3h 00m
Frontier
Deal found 4/6![Frontier logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:14 am
MDW
- MCO
Nonstop2h 49m
Frontier
Mon 5/49:49 pm
MCO
- MDW
1 stop14h 20m
Frontier
Deal found 4/7![Frontier logo]()
$139
This Frontier deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/292:15 pm
MDW
- MCO
1 stop9h 04m
Frontier
Wed 5/63:10 pm
MCO
- MDW
1 stop7h 52m
Frontier
Deal found 4/6![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 4/217:30 am
MDW
- MCO
1 stop14h 56m
Frontier
Fri 4/249:49 pm
MCO
- MDW
1 stop21h 48m
Frontier
Deal found 4/7![Frontier logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 4/135:30 am
MDW
- MCO
Nonstop2h 46m
Frontier
Thu 4/162:56 pm
MCO
- MDW
1 stop8h 23m
Frontier
Deal found 4/6![Frontier logo]()
$142
This Frontier deal was found by Cheapflights users on 4/6. 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 5/1312:04 pm
MDW
- MCO
1 stop6h 28m
Frontier
Mon 5/181:57 pm
MCO
- MDW
Nonstop3h 00m
Frontier
Deal found 4/6![Frontier logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 8/92:49 pm
MDW
- SFB
1 stop23h 22m
Allegiant Air
Sun 8/169:20 pm
SFB
- MDW
1 stop18h 39m
Allegiant Air
Deal found 4/7![Allegiant Air logo]()
$224
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 April 9, 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 April 9, 2026.
This Southwest deal was found by Cheapflights users on 4/4. 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 4/286:20 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Tue 5/58:55 am
MCO
- MDW
1 stop4h 05m
Southwest
Deal found 4/4![Southwest logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 8/92:49 pm
MDW
- SFB
1 stop23h 22m
Allegiant Air
Sun 8/169:20 pm
SFB
- MDW
1 stop18h 39m
Allegiant Air
Deal found 4/7![Allegiant Air logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 8/103:49 pm
MDW
- SFB
1 stop19h 08m
Multiple Airlines
Mon 8/179:04 pm
SFB
- MDW
2 stops26h 07m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$311
This Southwest deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:20 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Tue 5/198:55 am
MCO
- MDW
1 stop4h 05m
Southwest
Deal found 4/9![Southwest logo]()
$175
This Southwest deal was found by Cheapflights users on 4/6. 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 6/88:55 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Wed 6/178:00 am
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 4/6![Southwest logo]()
$184
This Southwest deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/274:50 pm
MDW
- MCO
Nonstop2h 40m
Southwest
Sat 5/301:50 pm
MCO
- MDW
1 stop4h 30m
Southwest
Deal found 4/5![Southwest logo]()
$190
This Southwest deal was found by Cheapflights users on 4/5. 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 6/611:05 am
MDW
- MCO
1 stop4h 55m
Southwest
Wed 6/104:40 pm
MCO
- MDW
1 stop4h 10m
Southwest
Deal found 4/5![Southwest logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 4/9. 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 6/158:20 pm
MDW
- SFB
1 stop14h 32m
Allegiant Air
Thu 6/188:56 pm
SFB
- MDW
1 stop23h 34m
Allegiant Air
Deal found 4/9![Allegiant Air logo]()
$269
This Southwest deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/139:25 am
MDW
- MCO
Nonstop2h 35m
Southwest
Sun 5/177:05 am
MCO
- MDW
Nonstop2h 55m
Southwest
Deal found 4/5![Southwest logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 4/9. 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 6/158:20 pm
MDW
- SFB
1 stop14h 32m
Multiple Airlines
Thu 6/189:25 pm
SFB
- MDW
2 stops25h 46m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 4/9. 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 7/192:48 pm
MDW
- SFB
1 stop4h 41m
Allegiant Air
Sun 7/268:58 pm
SFB
- MDW
1 stop18h 40m
Allegiant Air
Deal found 4/9![Allegiant Air logo]()
$327
This Southwest deal was found by Cheapflights users on 4/4. 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 5/105:05 am
MDW
- MCO
Nonstop2h 30m
Southwest
Thu 5/1410:20 pm
MCO
- MDW
Nonstop2h 55m
Southwest
Deal found 4/4![Southwest logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 8/22:48 pm
MDW
- SFB
1 stop4h 41m
Allegiant Air
Sat 8/88:25 pm
SFB
- MDW
1 stop18h 34m
Allegiant Air
Deal found 4/5![Allegiant Air logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 4/8![Allegiant Air logo]()
$335
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 6/228:20 pm
MDW
- SFB
1 stop14h 32m
Allegiant Air
Sat 6/278:15 pm
SFB
- MDW
1 stop18h 41m
Allegiant Air
Deal found 4/6![Allegiant Air logo]()
$337
This Southwest deal was found by Cheapflights users on 4/6. 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 5/255:35 am
MDW
- MCO
Nonstop2h 30m
Southwest
Thu 5/287:20 am
MCO
- MDW
Nonstop2h 55m
Southwest
Deal found 4/6![Southwest logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 5/293:42 pm
MDW
- SFB
1 stop21h 40m
Allegiant Air
Sat 6/68:15 pm
SFB
- MDW
1 stop18h 41m
Allegiant Air
Deal found 4/8![Allegiant Air logo]()
$347
This Southwest deal was found by Cheapflights users on 4/5. 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 6/174:35 pm
MDW
- MCO
Nonstop2h 45m
Southwest
Sun 6/2110:00 pm
MCO
- MDW
Nonstop2h 45m
Southwest
Deal found 4/5![Southwest logo]()
$303
This Southwest deal was found by Cheapflights users on 4/6. 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 6/108:10 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Mon 6/157:25 am
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 4/6![Southwest logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 6/212:46 pm
MDW
- SFB
1 stop25h 45m
Allegiant Air
Thu 6/258:58 pm
SFB
- MDW
1 stop21h 50m
Allegiant Air
Deal found 4/6![Allegiant Air logo]()
$369
This Southwest deal was found by Cheapflights users on 4/7. 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 6/24:50 pm
MDW
- MCO
Nonstop2h 40m
Southwest
Sun 6/72:10 pm
MCO
- MDW
1 stop4h 25m
Southwest
Deal found 4/7![Southwest logo]()
$309
Last-minute flights from Midway to Walt Disney WorldDiscover last-minute flight deals from Midway to Walt Disney World. Data last updated April 9, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Walt Disney World. Data last updated April 9, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 4/8. 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.
Mon 4/135:30 am
MDW
- MCO
Nonstop2h 46m
Frontier
Fri 4/176:00 am
MCO
- MDW
Nonstop2h 59m
Frontier
Deal found 4/8![Frontier logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 4/135:30 am
MDW
- MCO
Nonstop2h 46m
Frontier
Thu 4/162:56 pm
MCO
- MDW
1 stop8h 23m
Frontier
Deal found 4/6![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 4/212:15 pm
MDW
- MCO
1 stop19h 09m
Multiple Airlines
Fri 4/2411:18 am
MCO
- MDW
1 stop9h 13m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 4/217:30 am
MDW
- MCO
1 stop14h 56m
Frontier
Fri 4/249:49 pm
MCO
- MDW
1 stop21h 48m
Frontier
Deal found 4/7![Frontier logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:15 am
MDW
- MCO
1 stop8h 14m
Multiple Airlines
Wed 4/292:40 pm
MCO
- MDW
1 stop8h 34m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 4/257:34 pm
MDW
- MCO
1 stop11h 05m
Frontier
Wed 4/292:40 pm
MCO
- MDW
1 stop5h 51m
Frontier
Deal found 4/5![Frontier logo]()
$136
This Frontier deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/292:15 pm
MDW
- MCO
1 stop9h 04m
Frontier
Wed 5/63:10 pm
MCO
- MDW
1 stop7h 52m
Frontier
Deal found 4/6![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:14 am
MDW
- MCO
Nonstop2h 49m
Frontier
Mon 5/49:49 pm
MCO
- MDW
1 stop14h 20m
Frontier
Deal found 4/7![Frontier logo]()
$139
This Expedia deal was found by Cheapflights users on 4/8. 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.
Fri 5/84:52 pm
MDW
- MCO
Nonstop2h 47m
Frontier
Tue 5/123:10 pm
MCO
- MDW
1 stop7h 52m
Frontier
Deal found 4/8![Frontier logo]()
$134
This Frontier deal was found by Cheapflights users on 4/6. 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 5/1312:04 pm
MDW
- MCO
1 stop6h 28m
Frontier
Mon 5/181:57 pm
MCO
- MDW
Nonstop3h 00m
Frontier
Deal found 4/6![Frontier logo]()
$143
This Expedia deal was found by Cheapflights users on 4/6. 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.
Fri 5/154:52 pm
MDW
- MCO
Nonstop2h 47m
Frontier
Mon 5/181:57 pm
MCO
- MDW
Nonstop3h 00m
Frontier
Deal found 4/6![Frontier logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 5/293:42 pm
MDW
- SFB
1 stop21h 40m
Allegiant Air
Sat 6/68:15 pm
SFB
- MDW
1 stop18h 41m
Allegiant Air
Deal found 4/8![Allegiant Air logo]()
$347
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 April 9, 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 April 9, 2026.
This Priceline deal was found by Cheapflights users on 4/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:30 am
MDW
- MCO
Nonstop2h 46m
Frontier
Deal found 4/6![Frontier logo]()
$59
This Super.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/84:52 pm
MDW
- MCO
Nonstop2h 47m
Frontier
Deal found 4/6![Frontier logo]()
$63
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 4/216:10 am
MDW
- MCO
1 stop27h 14m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$64
This Trip.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:10 am
MDW
- MCO
1 stop6h 24m
Frontier
Deal found 4/5![Frontier logo]()
$66
This Trip.com deal was found by Cheapflights users on 4/4. 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.
Mon 4/206:00 am
MDW
- MCO
1 stop8h 29m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$67
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
MDW
- MCO
1 stop6h 37m
Frontier
Deal found 4/6![Frontier logo]()
$68
This Super.com deal was found by Cheapflights users on 4/6. 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 5/63:07 pm
MDW
- MCO
1 stop8h 03m
Frontier
Deal found 4/6![Frontier logo]()
$69
This Expedia deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/93:07 pm
MDW
- MCO
1 stop7h 29m
Frontier
Deal found 4/6![Frontier logo]()
$70
This Flightnetwork deal was found by Cheapflights users on 4/6. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/53:07 pm
MDW
- MCO
1 stop8h 03m
Frontier
Deal found 4/6![Frontier logo]()
$71
This Trip.com deal was found by Cheapflights users on 4/5. 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.
Sun 4/266:00 am
MDW
- MCO
1 stop6h 37m
Frontier
Deal found 4/5![Frontier logo]()
$73
This Kiwi.com deal was found by Cheapflights users on 4/9. 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 6/158:20 pm
MDW
- SFB
1 stop14h 32m
Allegiant Air
Deal found 4/9![Allegiant Air logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 4/4. 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 6/296:38 pm
MDW
- SFB
1 stop16h 14m
Allegiant Air
Deal found 4/4![Allegiant Air logo]()
$129
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 April 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $132 (Kiwi.com) |
One-way from | $59 (Priceline) |
Popular in | December |
Cheapest in | September |
Average price | $257 |
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 April 9, 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 - MCO
MDWMCO
Chicago Midway
Tue 4/28
6:20 pm-9:55 pm
Nonstop2h 35m
Orlando
Tue 5/5
8:55 am-12:00 pm
1 stop4h 05m
$175
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Wed 5/13
6:20 pm-9:55 pm
Nonstop2h 35m
Orlando
Tue 5/19
8:55 am-12:00 pm
1 stop4h 05m
$175
Quickest round-trip
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Mon 6/8
8:55 pm-12:30 am
Nonstop2h 35m
Orlando
Wed 6/17
8:00 am-9:50 am
Nonstop2h 50m
$184
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Wed 5/27
4:50 pm-8:30 pm
Nonstop2h 40m
Orlando
Sat 5/30
1:50 pm-5:20 pm
1 stop4h 30m
$190
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Sat 6/6
11:05 am-5:00 pm
1 stop4h 55m
Orlando
Wed 6/10
4:40 pm-7:50 pm
1 stop4h 10m
$199
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Wed 5/13
9:25 am-1:00 pm
Nonstop2h 35m
Orlando
Sun 5/17
7:05 am-9:00 am
Nonstop2h 55m
$213
ChicagoOrlando
MDW - SFB
MDWSFB
Chicago Midway
Sun 8/9
2:49 pm-3:11 pm
1 stop23h 22m
Orlando Sanford Intl
Sun 8/16
9:20 pm-2:59 pm
1 stop18h 39m
$224
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Sun 5/10
5:05 am-8:35 am
Nonstop2h 30m
Orlando
Thu 5/14
10:20 pm-12:15 am
Nonstop2h 55m
$228
ChicagoOrlando
MDW - SFB
MDWSFB
Chicago Midway
Mon 6/15
8:20 pm-11:52 am
1 stop14h 32m
Orlando Sanford Intl
Thu 6/18
8:56 pm-7:30 pm
1 stop23h 34m
$269
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Mon 5/25
5:35 am-9:05 am
Nonstop2h 30m
Orlando
Thu 5/28
7:20 am-9:15 am
Nonstop2h 55m
$279
Showing 1-10 of 41 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
How far ahead should I book a flight from Chicago Midway Airport to Walt Disney World?
Use this chart to determine the optimal time to book a round-trip flight from Midway to Walt Disney World. Price data was last updated on April 3, 2026.
The best time to book flights from Chicago Midway Airport to Walt Disney World is 49 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Chicago Midway Airport to Walt Disney World?
Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Walt Disney World (average of $58). Flying from Chicago Midway Airport to Walt Disney World in March is currently the most expensive (average of $145). 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 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 April 9, 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 23% on your trip compared to booking a flight at noon.
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 April 4, 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 mornings flights should be avoided if possible as fares are typically the most expensive at this time.
How much does it cost to fly round-trip from Chicago Midway Airport to Walt Disney World?
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 April 9, 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.
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
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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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 April 9, 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 April 9, 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 3 airlines flying from Midway to Walt Disney World
Discover the top 3 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 April 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$69 | Average$177 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$98 | Average$529 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$171 | Average$354 | FlexibilityNo cancel fee | On-time63% |