$86+ 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 6/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Jun 28 — Jul 51
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 90 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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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 May 29, 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 May 29, 2026.
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/75:30 pm
MDW
- MCO
Nonstop2h 50m
Southwest
Wed 7/88:10 pm
MCO
- MDW
Nonstop2h 55m
Southwest
Deal found 5/28![Southwest logo]()
$171
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:10 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Tue 7/146:10 pm
MCO
- MDW
Nonstop3h 00m
Southwest
Deal found 5/26![Southwest logo]()
$180
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/15:20 pm
MDW
- MCO
1 stop5h 20m
Southwest
Wed 7/2211:00 am
MCO
- MDW
Nonstop2h 45m
Southwest
Deal found 5/28![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/83:00 pm
MDW
- MCO
1 stop3h 55m
Southwest
Tue 7/214:40 pm
MCO
- MDW
1 stop4h 10m
Southwest
Deal found 5/27![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/153:40 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Wed 8/197:15 pm
MCO
- MDW
Nonstop2h 45m
Southwest
Deal found 5/28![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 5/24. 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.
Tue 7/75:30 pm
MDW
- MCO
Nonstop2h 50m
Southwest
Tue 7/148:10 pm
MCO
- MDW
Nonstop2h 55m
Southwest
Deal found 5/24![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/235:30 pm
MDW
- MCO
Nonstop2h 45m
Southwest
Tue 6/307:45 pm
MCO
- MDW
1 stop4h 25m
Southwest
Deal found 5/26![Southwest logo]()
$190
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/305:20 pm
MDW
- MCO
1 stop5h 20m
Southwest
Tue 7/74:40 pm
MCO
- MDW
1 stop5h 30m
Southwest
Deal found 5/27![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:40 am
MDW
- MCO
2 stops5h 55m
Southwest
Tue 8/189:00 am
MCO
- MDW
1 stop4h 05m
Southwest
Deal found 5/28![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:15 am
MDW
- MCO
Nonstop2h 30m
Southwest
Sat 8/291:25 pm
MCO
- MDW
1 stop4h 40m
Southwest
Deal found 5/28![Southwest logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/62:49 pm
MDW
- SFB
1 stop23h 22m
Allegiant Air
Sun 8/99:20 pm
SFB
- MDW
1 stop18h 39m
Allegiant Air
Deal found 5/25![Allegiant Air logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/62:49 pm
MDW
- SFB
1 stop23h 22m
Allegiant Air
Thu 8/139:20 pm
SFB
- MDW
1 stop18h 39m
Allegiant Air
Deal found 5/28![Allegiant Air logo]()
$234
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 May 29, 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 May 29, 2026.
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/176:00 am
MDW
- MCO
1 stop5h 00m
Delta
Tue 6/235:30 am
MCO
- MDW
1 stop5h 39m
Delta
Deal found 5/27![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:50 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Thu 10/297:55 am
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 5/26![Southwest logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/62:49 pm
MDW
- SFB
1 stop23h 22m
Allegiant Air
Sun 8/99:20 pm
SFB
- MDW
1 stop18h 39m
Allegiant Air
Deal found 5/25![Allegiant Air logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:05 am
MDW
- SFB
2 stops35h 12m
Multiple Airlines
Sun 7/128:58 pm
SFB
- MDW
1 stop18h 40m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/247:55 am
MDW
- MCO
Nonstop2h 35m
Southwest
Wed 6/248:10 pm
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 5/26![Southwest logo]()
$211
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:10 pm
MDW
- MCO
1 stop6h 58m
Delta
Mon 9/216:15 am
MCO
- MDW
1 stop4h 38m
Delta
Deal found 5/27![Delta logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/62:49 pm
MDW
- SFB
1 stop23h 22m
Allegiant Air
Thu 8/139:20 pm
SFB
- MDW
1 stop18h 39m
Allegiant Air
Deal found 5/28![Allegiant Air logo]()
$234
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/131:00 pm
MDW
- MCO
1 stop5h 15m
Southwest
Sat 8/221:25 pm
MCO
- MDW
1 stop4h 40m
Southwest
Deal found 5/27![Southwest logo]()
$214
This Southwest deal was found by Cheapflights users on 5/24. 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.
Tue 6/305:20 pm
MDW
- MCO
1 stop5h 20m
Southwest
Sat 7/41:15 pm
MCO
- MDW
1 stop4h 35m
Southwest
Deal found 5/24![Southwest logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/33:28 pm
MDW
- SFB
1 stop7h 07m
Allegiant Air
Sun 8/99:20 pm
SFB
- MDW
1 stop18h 39m
Allegiant Air
Deal found 5/25![Allegiant Air logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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 5/25![Allegiant Air logo]()
$251
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/285:10 pm
MDW
- MCO
1 stop4h 52m
Delta
Sun 8/25:30 am
MCO
- MDW
1 stop5h 35m
Delta
Deal found 5/28![Delta logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/33:28 pm
MDW
- SFB
1 stop7h 07m
Allegiant Air
Sat 7/118:19 pm
SFB
- MDW
1 stop18h 39m
Allegiant Air
Deal found 5/28![Allegiant Air logo]()
$256
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:25 pm
MDW
- MCO
1 stop6h 31m
Delta
Sun 10/255:30 am
MCO
- MDW
1 stop5h 22m
Delta
Deal found 5/28![Delta logo]()
$291
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/277:35 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Tue 6/307:45 pm
MCO
- MDW
1 stop4h 25m
Southwest
Deal found 5/28![Southwest logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/92:48 pm
MDW
- SFB
1 stop25h 33m
Allegiant Air
Thu 7/168:58 pm
SFB
- MDW
1 stop18h 40m
Allegiant Air
Deal found 5/24![Allegiant Air logo]()
$259
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/42:55 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Mon 9/76:55 am
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 5/28![Southwest logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/282:46 pm
MDW
- SFB
1 stop25h 40m
Allegiant Air
Wed 7/15:18 pm
SFB
- MDW
1 stop21h 40m
Allegiant Air
Deal found 5/27![Allegiant Air logo]()
$277
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:10 pm
MDW
- MCO
Nonstop2h 45m
Southwest
Mon 7/61:45 pm
MCO
- MDW
1 stop5h 05m
Southwest
Deal found 5/28![Southwest logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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
Sat 6/208:15 pm
SFB
- MDW
1 stop18h 41m
Allegiant Air
Deal found 5/29![Allegiant Air logo]()
$283
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:50 pm
MDW
- MCO
1 stop5h 15m
Southwest
Mon 10/57:25 am
MCO
- MDW
2 stops7h 30m
Southwest
Deal found 5/28![Southwest logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 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 5/25![Allegiant Air logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/52:48 pm
MDW
- SFB
1 stop25h 33m
Allegiant Air
Sun 7/128:58 pm
SFB
- MDW
1 stop18h 40m
Allegiant Air
Deal found 5/28![Allegiant Air logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/282:46 pm
MDW
- SFB
1 stop25h 40m
Allegiant Air
Sun 7/58:58 pm
SFB
- MDW
1 stop18h 40m
Allegiant Air
Deal found 5/28![Allegiant Air logo]()
$314
Last-minute flights from Midway to Walt Disney WorldDiscover last-minute flight deals from Midway to Walt Disney World. Data last updated May 29, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Walt Disney World. Data last updated May 29, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/158:20 pm
MDW
- SFB
1 stop14h 32m
Allegiant Air
Sun 6/218:56 pm
SFB
- MDW
1 stop23h 34m
Allegiant Air
Deal found 5/28![Allegiant Air logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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
Sat 6/208:15 pm
SFB
- MDW
1 stop18h 41m
Allegiant Air
Deal found 5/29![Allegiant Air logo]()
$283
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/165:11 pm
MDW
- MCO
1 stop5h 41m
Delta
Tue 6/235:30 am
MCO
- MDW
1 stop5h 39m
Delta
Deal found 5/26![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1612:50 pm
MDW
- MCO
1 stop4h 55m
Southwest
Tue 6/168:10 pm
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 5/26![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/175:30 pm
MDW
- MCO
Nonstop2h 45m
Southwest
Tue 6/237:10 am
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 5/26![Southwest logo]()
$171
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/235:30 pm
MDW
- MCO
Nonstop2h 45m
Southwest
Tue 6/307:45 pm
MCO
- MDW
1 stop4h 25m
Southwest
Deal found 5/26![Southwest logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/282:46 pm
MDW
- SFB
1 stop25h 40m
Allegiant Air
Wed 7/15:18 pm
SFB
- MDW
1 stop21h 40m
Allegiant Air
Deal found 5/27![Allegiant Air logo]()
$277
This Southwest deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:10 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Tue 7/144:40 pm
MCO
- MDW
1 stop4h 10m
Southwest
Deal found 5/25![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:10 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Wed 7/18:50 am
MCO
- MDW
1 stop4h 35m
Southwest
Deal found 5/28![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/305:20 pm
MDW
- MCO
1 stop5h 20m
Southwest
Tue 7/74:40 pm
MCO
- MDW
1 stop5h 30m
Southwest
Deal found 5/27![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:10 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Sat 7/46:40 am
MCO
- MDW
Nonstop2h 45m
Southwest
Deal found 5/28![Southwest logo]()
$194
This Southwest deal was found by Cheapflights users on 5/24. 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.
Tue 6/308:10 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Wed 7/84:40 pm
MCO
- MDW
1 stop4h 10m
Southwest
Deal found 5/24![Southwest logo]()
$195
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 May 29, 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 May 29, 2026.
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/304:40 pm
MDW
- MCO
Nonstop2h 45m
Southwest
Deal found 5/27![Southwest logo]()
$86
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/293:00 pm
MDW
- MCO
1 stop3h 55m
Southwest
Deal found 5/26![Southwest logo]()
$91
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/235:30 pm
MDW
- MCO
Nonstop2h 45m
Southwest
Deal found 5/26![Southwest logo]()
$95
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/159:19 am
MDW
- MCO
1 stop6h 27m
Delta
Deal found 5/28![Delta logo]()
$99
This Southwest deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/143:00 pm
MDW
- MCO
1 stop3h 55m
Southwest
Deal found 5/25![Southwest logo]()
$100
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:40 am
MDW
- MCO
2 stops5h 55m
Southwest
Deal found 5/28![Southwest logo]()
$101
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/107:50 pm
MDW
- MCO
Nonstop2h 30m
Southwest
Deal found 5/27![Southwest logo]()
$102
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/87:50 am
MDW
- MCO
1 stop4h 05m
Southwest
Deal found 5/27![Southwest logo]()
$107
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:35 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Deal found 5/28![Southwest logo]()
$109
This Southwest deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:40 am
MDW
- MCO
2 stops5h 55m
Southwest
Deal found 5/25![Southwest logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/243:28 pm
MDW
- SFB
1 stop7h 07m
Allegiant Air
Deal found 5/27![Allegiant Air logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/162:49 pm
MDW
- SFB
1 stop23h 22m
Allegiant Air
Deal found 5/27![Allegiant Air logo]()
$117
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 May 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $171 (Southwest) |
One-way from | $86 (Southwest) |
Popular in | December |
Cheapest in | September |
Average price | $333 |
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 May 29, 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
Wed 6/17
6:00 am-12:00 pm
1 stop5h 00m
Orlando
Tue 6/23
5:30 am-10:09 am
1 stop5h 39m
$197
Quickest round-trip
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Thu 10/22
8:50 pm-12:25 am
Nonstop2h 35m
Orlando
Thu 10/29
7:55 am-9:45 am
Nonstop2h 50m
$203
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Wed 6/24
7:55 am-11:30 am
Nonstop2h 35m
Orlando
Wed 6/24
8:10 pm-10:00 pm
Nonstop2h 50m
$211
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Thu 8/13
1:00 pm-7:15 pm
1 stop5h 15m
Orlando
Sat 8/22
1:25 pm-5:05 pm
1 stop4h 40m
$214
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Thu 9/17
5:10 pm-1:08 am
1 stop6h 58m
Orlando
Mon 9/21
6:15 am-9:53 am
1 stop4h 38m
$223
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Tue 6/30
5:20 pm-11:40 pm
1 stop5h 20m
Orlando
Sat 7/4
1:15 pm-4:50 pm
1 stop4h 35m
$223
ChicagoOrlando
MDW - SFB
MDWSFB
Chicago Midway
Thu 8/6
2:49 pm-3:11 pm
1 stop23h 22m
Orlando Sanford Intl
Sun 8/9
9:20 pm-2:59 pm
1 stop18h 39m
$232
ChicagoOrlando
MDW - SFB
MDWSFB
Chicago Midway
Thu 8/6
2:49 pm-3:11 pm
1 stop23h 22m
Orlando Sanford Intl
Thu 8/13
9:20 pm-2:59 pm
1 stop18h 39m
$234
ChicagoOrlando
MDW - SFB
MDWSFB
Chicago Midway
Mon 8/3
3:28 pm-11:35 pm
1 stop7h 07m
Orlando Sanford Intl
Sun 8/9
9:20 pm-2:59 pm
1 stop18h 39m
$249
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
$251
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 May 29, 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 21% 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?
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 May 23, 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 May 29, 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.
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
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 May 29, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on May 29, 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 May 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$70 | Average$179 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$171 | Average$366 | FlexibilityNo cancel fee | On-time63% |