$63+ Cheap flights from Midway (MDW) to Florida
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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MIA
May 28 — Jun 41
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Florida with Cheapflights
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Cheapest flights from Midway to FloridaExplore the most affordable flight options available from Midway to Florida. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 28, 2026.
Explore the most affordable flight options available from Midway to Florida. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Tue 5/1212:24 pm
MDW
- FLL
1 stop17h 46m
Multiple Airlines
Wed 5/133:11 pm
FLL
- MDW
1 stop7h 51m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Tue 5/1212:24 pm
MDW
- FLL
1 stop17h 46m
Multiple Airlines
Tue 5/192:18 pm
FLL
- MDW
1 stop8h 44m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1212:24 pm
MDW
- MIA
1 stop9h 23m
Multiple Airlines
Thu 5/1411:06 am
MIA
- MDW
1 stop11h 56m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Thu 5/1412:19 pm
MDW
- FLL
1 stop9h 53m
Multiple Airlines
Mon 5/1810:02 pm
FLL
- MDW
1 stop14h 07m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 5/1412:19 pm
MDW
- FLL
1 stop9h 53m
Multiple Airlines
Tue 5/196:05 am
FLL
- MDW
1 stop6h 04m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:04 pm
MDW
- FLL
1 stop11h 40m
Frontier
Tue 6/29:15 pm
FLL
- MDW
1 stop25h 47m
Frontier
Deal found 4/26![Frontier logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Wed 5/136:00 am
MDW
- MIA
1 stop6h 20m
Frontier
Mon 5/188:10 am
MIA
- MDW
1 stop27h 59m
Frontier
Deal found 4/27![Frontier logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
Tue 5/1212:24 pm
MDW
- FLL
1 stop22h 33m
Multiple Airlines
Sat 5/166:05 am
FLL
- MDW
1 stop16h 57m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:00 am
MDW
- MIA
1 stop10h 10m
Multiple Airlines
Mon 5/1111:06 am
MIA
- MDW
1 stop25h 03m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Tue 5/196:00 am
MDW
- FLL
1 stop6h 23m
Frontier
Tue 5/266:05 am
FLL
- MDW
1 stop16h 57m
Frontier
Deal found 4/27![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Wed 5/1312:04 pm
MDW
- MIA
1 stop9h 43m
Frontier
Tue 5/265:22 pm
MIA
- MDW
1 stop5h 40m
Frontier
Deal found 4/27![Frontier logo]()
$140
This Frontier deal was found by Cheapflights users on 4/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1912:24 pm
MDW
- MCO
1 stop8h 23m
Frontier
Wed 5/203:10 pm
MCO
- MDW
1 stop7h 52m
Frontier
Deal found 4/27![Frontier logo]()
$140
Best flights from Midway to FloridaDiscover carefully curated flight deals from Midway to Florida that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 28, 2026.
Discover carefully curated flight deals from Midway to Florida that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 28, 2026.
This Southwest deal was found by Cheapflights users on 4/27. 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 5/266:10 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Thu 5/286:40 pm
FLL
- MDW
Nonstop3h 10m
Southwest
Deal found 4/27![Southwest logo]()
$184
This Delta deal was found by Cheapflights users on 4/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/39:22 am
MDW
- FLL
1 stop5h 05m
Delta
Wed 6/1011:05 am
FLL
- MDW
1 stop6h 11m
Delta
Deal found 4/25![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 4/26. 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 5/277:40 am
MDW
- FLL
Nonstop2h 55m
Southwest
Sat 5/308:10 am
FLL
- MDW
1 stop6h 00m
Southwest
Deal found 4/26![Southwest logo]()
$194
This Southwest deal was found by Cheapflights users on 4/27. 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 5/191:55 pm
MDW
- MCO
1 stop4h 25m
Southwest
Thu 5/2110:20 pm
MCO
- MDW
Nonstop2h 55m
Southwest
Deal found 4/27![Southwest logo]()
$194
This Delta deal was found by Cheapflights users on 4/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/301:22 pm
MDW
- FLL
1 stop4h 41m
Delta
Sat 6/66:00 am
FLL
- MDW
1 stop7h 42m
Delta
Deal found 4/25![Delta logo]()
$219
This Southwest deal was found by Cheapflights users on 4/25. 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.
Mon 5/188:35 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Wed 5/207:15 am
MCO
- MDW
Nonstop2h 55m
Southwest
Deal found 4/25![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 4/26. 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.
Sat 5/234:00 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Tue 5/263:25 pm
FLL
- MDW
1 stop5h 45m
Southwest
Deal found 4/26![Southwest logo]()
$209
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:23 am
MDW
- ECP
1 stop6h 27m
Delta
Tue 5/199:19 am
ECP
- MDW
1 stop6h 53m
Delta
Deal found 4/23![Delta logo]()
$265
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/310:59 am
MDW
- RSW
1 stop5h 01m
Delta
Thu 6/116:34 pm
RSW
- MDW
1 stop4h 43m
Delta
Deal found 4/23![Delta logo]()
$266
This Southwest deal was found by Cheapflights users on 4/27. 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 5/3012:05 pm
MDW
- TPA
2 stops7h 10m
Southwest
Mon 6/18:00 pm
TPA
- MDW
1 stop4h 30m
Southwest
Deal found 4/27![Southwest logo]()
$224
This Delta deal was found by Cheapflights users on 4/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:10 pm
MDW
- ECP
1 stop5h 41m
Delta
Sat 6/63:00 pm
ECP
- MDW
1 stop6h 09m
Delta
Deal found 4/24![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 4/26. 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 6/247:45 am
MDW
- TPA
1 stop5h 55m
Southwest
Wed 6/249:55 pm
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 4/26![Southwest logo]()
$251
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/267:55 am
MDW
- MIA
Nonstop3h 00m
Southwest
Thu 5/286:05 am
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 4/23![Southwest logo]()
$253
This Delta deal was found by Cheapflights users on 4/26. 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.
Wed 7/16:00 am
MDW
- PBI
1 stop4h 46m
Delta
Tue 7/710:00 am
PBI
- MDW
1 stop7h 15m
Delta
Deal found 4/26![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 4/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/236:05 am
MDW
- PBI
1 stop5h 49m
Delta
Tue 7/1410:00 am
PBI
- MDW
1 stop7h 15m
Delta
Deal found 4/24![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/175:30 am
MDW
- TPA
Nonstop2h 30m
Southwest
Mon 6/2210:30 pm
TPA
- MDW
Nonstop2h 35m
Southwest
Deal found 4/24![Southwest logo]()
$256
This Delta deal was found by Cheapflights users on 4/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:10 pm
MDW
- PBI
1 stop6h 39m
Delta
Sun 5/316:00 am
PBI
- MDW
1 stop5h 00m
Delta
Deal found 4/24![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/56:55 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Wed 6/107:10 am
RSW
- MDW
Nonstop2h 50m
Southwest
Deal found 4/23![Southwest logo]()
$258
This Delta deal was found by Cheapflights users on 4/27. 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.
Fri 6/1211:05 am
MDW
- PBI
1 stop5h 18m
Delta
Sun 6/146:00 am
PBI
- MDW
1 stop5h 09m
Delta
Deal found 4/27![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 4/25. 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 5/1312:55 pm
MDW
- MCO
1 stop6h 00m
Southwest
Wed 5/207:15 am
MCO
- MDW
Nonstop2h 55m
Southwest
Deal found 4/25![Southwest logo]()
$264
This Delta deal was found by Cheapflights users on 4/26. 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.
Sat 5/2310:45 am
MDW
- PBI
1 stop6h 47m
Delta
Tue 5/264:52 pm
PBI
- MDW
1 stop5h 17m
Delta
Deal found 4/26![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 4/26. 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 6/238:15 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Sat 6/275:30 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 4/26![Southwest logo]()
$265
This Delta deal was found by Cheapflights users on 4/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/610:45 am
MDW
- PBI
1 stop5h 44m
Delta
Sat 6/135:06 pm
PBI
- MDW
1 stop6h 11m
Delta
Deal found 4/25![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/162:15 pm
MDW
- RSW
1 stop4h 50m
Southwest
Wed 5/206:40 pm
RSW
- MDW
1 stop4h 35m
Southwest
Deal found 4/23![Southwest logo]()
$270
This Delta deal was found by Cheapflights users on 4/27. 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 5/285:10 pm
MDW
- PBI
1 stop6h 38m
Delta
Sun 5/316:00 am
PBI
- MDW
1 stop5h 00m
Delta
Deal found 4/27![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 4/25. 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 6/166:55 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Mon 6/295:55 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 4/25![Southwest logo]()
$271
This Delta deal was found by Cheapflights users on 4/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1512:53 pm
MDW
- PBI
1 stop6h 20m
Delta
Sun 5/174:52 pm
PBI
- MDW
1 stop5h 17m
Delta
Deal found 4/24![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/28:00 am
MDW
- PBI
1 stop6h 15m
Southwest
Sat 6/66:30 am
PBI
- MDW
2 stops7h 05m
Southwest
Deal found 4/23![Southwest logo]()
$279
This Delta deal was found by Cheapflights users on 4/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/410:59 am
MDW
- SRQ
1 stop6h 44m
Delta
Wed 6/106:00 am
SRQ
- MDW
2 stops13h 18m
Delta
Deal found 4/25![Delta logo]()
$311
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/38:00 am
MDW
- PBI
1 stop6h 15m
Southwest
Sat 6/611:35 am
PBI
- MDW
2 stops11h 20m
Southwest
Deal found 4/23![Southwest logo]()
$279
Last-minute flights from Midway to FloridaDiscover last-minute flight deals from Midway to Florida. Data last updated April 28, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Florida. Data last updated April 28, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:00 am
MDW
- MIA
1 stop10h 10m
Multiple Airlines
Mon 5/1111:06 am
MIA
- MDW
1 stop25h 03m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Tue 5/1212:24 pm
MDW
- FLL
1 stop17h 46m
Multiple Airlines
Wed 5/133:11 pm
FLL
- MDW
1 stop7h 51m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Tue 5/1212:24 pm
MDW
- FLL
1 stop17h 46m
Multiple Airlines
Tue 5/192:18 pm
FLL
- MDW
1 stop8h 44m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1212:24 pm
MDW
- MIA
1 stop9h 23m
Multiple Airlines
Thu 5/1411:06 am
MIA
- MDW
1 stop11h 56m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
Tue 5/1212:24 pm
MDW
- FLL
1 stop22h 33m
Multiple Airlines
Sat 5/166:05 am
FLL
- MDW
1 stop16h 57m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Wed 5/136:00 am
MDW
- MIA
1 stop6h 20m
Frontier
Mon 5/188:10 am
MIA
- MDW
1 stop27h 59m
Frontier
Deal found 4/27![Frontier logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Wed 5/1312:04 pm
MDW
- MIA
1 stop9h 43m
Frontier
Tue 5/265:22 pm
MIA
- MDW
1 stop5h 40m
Frontier
Deal found 4/27![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Thu 5/1412:19 pm
MDW
- FLL
1 stop9h 53m
Multiple Airlines
Mon 5/1810:02 pm
FLL
- MDW
1 stop14h 07m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 5/1412:19 pm
MDW
- FLL
1 stop9h 53m
Multiple Airlines
Tue 5/196:05 am
FLL
- MDW
1 stop6h 04m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Tue 5/196:00 am
MDW
- FLL
1 stop6h 23m
Frontier
Tue 5/266:05 am
FLL
- MDW
1 stop16h 57m
Frontier
Deal found 4/27![Frontier logo]()
$140
This Frontier deal was found by Cheapflights users on 4/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1912:24 pm
MDW
- MCO
1 stop8h 23m
Frontier
Wed 5/203:10 pm
MCO
- MDW
1 stop7h 52m
Frontier
Deal found 4/27![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:04 pm
MDW
- FLL
1 stop11h 40m
Frontier
Tue 6/29:15 pm
FLL
- MDW
1 stop25h 47m
Frontier
Deal found 4/26![Frontier logo]()
$136
One-way flights from Midway to FloridaSearch for one-way flight options from Midway to Florida. Find affordable one-way fares based on user searches. Data last updated April 28, 2026.
Search for one-way flight options from Midway to Florida. Find affordable one-way fares based on user searches. Data last updated April 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 5/154:52 pm
MDW
- MCO
Nonstop2h 47m
Frontier
Deal found 4/27![Frontier logo]()
$63
This CheapOair deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/38:39 am
MDW
- MCO
Nonstop2h 51m
Frontier
Deal found 4/23![Frontier logo]()
$64
This Trip.com deal was found by Cheapflights users on 4/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 am
MDW
- FLL
1 stop17h 44m
Frontier
Deal found 4/27![Frontier logo]()
$66
This Trip.com deal was found by Cheapflights users on 4/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:04 pm
MDW
- MIA
1 stop9h 43m
Frontier
Deal found 4/27![Frontier logo]()
$66
This Trip.com deal was found by Cheapflights users on 4/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1912:24 pm
MDW
- MCO
1 stop6h 08m
Frontier
Deal found 4/27![Frontier logo]()
$66
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Tue 5/126:00 am
MDW
- FLL
1 stop28h 57m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$67
This Trip.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1012:04 pm
MDW
- MIA
1 stop9h 59m
Frontier
Deal found 4/23![Frontier logo]()
$67
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/146:00 am
MDW
- FLL
1 stop17h 44m
Frontier
Deal found 4/23![Frontier logo]()
$68
This Jetabroad deal was found by Cheapflights users on 4/27. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/48:41 am
MDW
- MCO
Nonstop2h 51m
Frontier
Deal found 4/27![Frontier logo]()
$68
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Thu 5/1412:19 pm
MDW
- FLL
1 stop9h 53m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$69
This Trip.com deal was found by Cheapflights users on 4/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/212:27 pm
MDW
- FLL
1 stop11h 17m
Frontier
Deal found 4/27![Frontier logo]()
$70
This Frontier deal was found by Cheapflights users on 4/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2012:04 pm
MDW
- JAX
1 stop4h 31m
Frontier
Deal found 4/27![Frontier logo]()
$70
Find flight deals from Midway to Florida
Keep the following information in mind while searching for Midway to Florida flight deals. Data was last updated April 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $131 (Kiwi.com) |
One-way from | $63 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $243 |
Good round-trip deal | $138 or less |
Good one-way deal | $49 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Florida 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 28, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Florida that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Tue 5/26
6:10 pm-10:05 pm
Nonstop2h 55m
Fort Lauderdale
Thu 5/28
6:40 pm-8:50 pm
Nonstop3h 10m
$184
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Wed 5/27
7:40 am-11:35 am
Nonstop2h 55m
Fort Lauderdale
Sat 5/30
8:10 am-1:10 pm
1 stop6h 00m
$194
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Tue 5/19
1:55 pm-7:20 pm
1 stop4h 25m
Orlando
Thu 5/21
10:20 pm-12:15 am
Nonstop2h 55m
$194
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Mon 5/18
8:35 pm-12:10 am
Nonstop2h 35m
Orlando
Wed 5/20
7:15 am-9:10 am
Nonstop2h 55m
$199
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Sat 5/23
4:00 pm-7:55 pm
Nonstop2h 55m
Fort Lauderdale
Tue 5/26
3:25 pm-8:10 pm
1 stop5h 45m
$209
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Wed 6/3
9:22 am-3:27 pm
1 stop5h 05m
Fort Lauderdale
Wed 6/10
11:05 am-4:16 pm
1 stop6h 11m
$217
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Sat 5/30
1:22 pm-7:03 pm
1 stop4h 41m
Fort Lauderdale
Sat 6/6
6:00 am-12:42 pm
1 stop7h 42m
$219
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Sat 5/30
12:05 pm-8:15 pm
2 stops7h 10m
Tampa
Mon 6/1
8:00 pm-11:30 pm
1 stop4h 30m
$224
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Wed 6/24
7:45 am-2:40 pm
1 stop5h 55m
Tampa
Wed 6/24
9:55 pm-11:35 pm
Nonstop2h 40m
$251
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 5/26
7:55 am-11:55 am
Nonstop3h 00m
Miami
Thu 5/28
6:05 am-8:20 am
Nonstop3h 15m
$253
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Midway to Florida
Have a flexible travel schedule? Discover the best time to fly to Florida from Midway with our price prediction graph.
MDW-FLL
MDW-MIA
MDW-MCO
MDW-ECP
MDW-RSW
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 Florida
MDW-USFL
MDW-FLL
MDW-MIA
MDW-MCO
MDW-ECP
How far ahead should I book a flight from Chicago Midway Airport to Florida?
The best time to book flights from Chicago Midway Airport to Florida is 22 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 Florida?
Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Florida (average of $27). Flying from Chicago Midway Airport to Florida in April is currently the most expensive (average of $785). 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 FL?
Find hourly flight availability from Midway to Florida. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 28, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 3% on flights from Chicago Midway Airport to Florida by exploring options for tickets at noon.
What is the cheapest day to fly from Chicago Midway Airport to Florida?
Use this chart to determine the cheapest time to fly round-trip from Midway to Florida. Price data was last updated on April 25, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Florida flight should consider departing on Wednesday at noon when fares are most often at their lowest. Saturday evenings 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 Florida?
Reviews of airlines servicing Florida
Get insights into the airlines that provide service to Florida. 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 Florida. Reviews last updated April 28, 2026.
Read reviews from past customers who have flown Southwest,Delta, andAllegiant Air from Chicago Midway Airport to Florida. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
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 Florida. 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 Florida
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Florida by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Florida by cabin class
Find flights from Midway to Florida, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Florida flights
Browse other Midway and Florida flight options. Last updated on April 28, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Midway to Florida flights
Consider these flights traveling from Midway to Florida.
Top 5 airlines flying from Midway to Florida
Discover the top 5 airlines that operate flights from Midway to Florida. 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 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$58 | Average$179 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$84 | Average$214 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$98 | Average$361 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$170 | Average$375 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$203 | Average$391 | FlexibilityNo cancel fee | On-time71% |