$85+ 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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MIA
Aug 27 — Sep 31
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 July 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 July 28, 2026.
This Southwest deal was found by Cheapflights users on 7/28. 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 8/256:10 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Wed 8/264:55 pm
FLL
- MDW
Nonstop3h 05m
Southwest
Deal found 7/28![Southwest logo]()
$149
This Southwest deal was found by Cheapflights users on 7/27. 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 8/198:15 am
MDW
- FLL
1 stop4h 40m
Southwest
Wed 8/267:20 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 7/27![Southwest logo]()
$159
This Southwest deal was found by Cheapflights users on 7/27. 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 8/186:10 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Thu 8/207:10 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 7/27![Southwest logo]()
$160
This Southwest deal was found by Cheapflights users on 7/28. 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 8/1912:50 pm
MDW
- FLL
2 stops6h 10m
Southwest
Tue 8/254:55 pm
FLL
- MDW
Nonstop3h 05m
Southwest
Deal found 7/28![Southwest logo]()
$164
This Southwest deal was found by Cheapflights users on 7/27. 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 8/2210:10 am
MDW
- FLL
1 stop4h 10m
Southwest
Tue 8/254:55 pm
FLL
- MDW
Nonstop3h 05m
Southwest
Deal found 7/27![Southwest logo]()
$166
This Southwest deal was found by Cheapflights users on 7/27. 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 8/206:20 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Mon 8/247:10 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 7/27![Southwest logo]()
$171
This Southwest deal was found by Cheapflights users on 7/26. 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.
Mon 8/317:40 am
MDW
- FLL
Nonstop2h 55m
Southwest
Sun 9/67:45 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 7/26![Southwest logo]()
$176
This Southwest deal was found by Cheapflights users on 7/27. 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 8/2210:10 am
MDW
- FLL
1 stop4h 10m
Southwest
Mon 8/247:10 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 7/27![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 7/27. 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 9/103:10 pm
MDW
- MIA
2 stops6h 00m
Southwest
Mon 9/147:15 am
MIA
- MDW
Nonstop3h 05m
Southwest
Deal found 7/27![Southwest logo]()
$186
This Southwest deal was found by Cheapflights users on 7/27. 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 8/178:00 am
MDW
- MIA
Nonstop3h 10m
Southwest
Sat 8/226:30 am
MIA
- MDW
1 stop5h 10m
Southwest
Deal found 7/27![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 7/27. 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 9/129:05 am
MDW
- MIA
2 stops9h 15m
Southwest
Sat 9/196:30 am
MIA
- MDW
1 stop5h 10m
Southwest
Deal found 7/27![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 7/27. 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 8/203:10 pm
MDW
- MIA
2 stops5h 55m
Southwest
Mon 8/247:00 am
MIA
- MDW
2 stops6h 25m
Southwest
Deal found 7/27![Southwest logo]()
$201
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 July 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 July 28, 2026.
This Southwest deal was found by Cheapflights users on 7/27. 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 8/258:35 am
MDW
- FLL
Nonstop3h 05m
Southwest
Sat 8/296:40 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 7/27![Southwest logo]()
$160
This Delta deal was found by Cheapflights users on 7/27. 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.
Sat 10/1011:33 am
MDW
- FLL
1 stop7h 06m
Delta
Tue 10/1312:09 pm
FLL
- MDW
1 stop5h 10m
Delta
Deal found 7/27![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:15 am
MDW
- FLL
1 stop4h 40m
Southwest
Wed 8/267:20 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 7/23![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 7/27. 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.
Sun 9/69:30 am
MDW
- FLL
2 stops10h 55m
Southwest
Thu 9/107:10 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 7/27![Southwest logo]()
$191
This Delta deal was found by Cheapflights users on 7/25. 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 9/264:30 pm
MDW
- FLL
1 stop7h 10m
Delta
Tue 9/299:59 am
FLL
- MDW
1 stop7h 16m
Delta
Deal found 7/25![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:05 am
MDW
- FLL
2 stops6h 35m
Southwest
Thu 9/246:35 pm
FLL
- MDW
1 stop4h 50m
Southwest
Deal found 7/24![Southwest logo]()
$192
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:35 am
MDW
- FLL
1 stop6h 01m
Delta
Mon 9/146:18 pm
FLL
- MDW
1 stop5h 26m
Delta
Deal found 7/23![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 7/27. 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 8/276:20 am
MDW
- FLL
1 stop6h 20m
Southwest
Mon 8/317:00 am
FLL
- MDW
2 stops6h 25m
Southwest
Deal found 7/27![Southwest logo]()
$196
This Delta deal was found by Cheapflights users on 7/27. 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.
Tue 8/186:05 am
MDW
- JAX
1 stop4h 39m
Delta
Tue 8/186:59 pm
JAX
- MDW
1 stop4h 37m
Delta
Deal found 7/27![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 7/28. 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 9/103:10 pm
MDW
- MIA
2 stops6h 00m
Southwest
Mon 9/147:15 am
MIA
- MDW
Nonstop3h 05m
Southwest
Deal found 7/28![Southwest logo]()
$196
This Delta deal was found by Cheapflights users on 7/26. 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.
Thu 8/209:24 am
MDW
- JAX
1 stop7h 01m
Delta
Wed 8/265:34 pm
JAX
- MDW
1 stop6h 02m
Delta
Deal found 7/26![Delta logo]()
$217
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:11 am
MDW
- JAX
1 stop6h 25m
Delta
Tue 9/156:00 am
JAX
- MDW
1 stop4h 49m
Delta
Deal found 7/24![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 7/27. 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 8/2712:10 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Wed 9/211:35 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 7/27![Southwest logo]()
$209
This Delta deal was found by Cheapflights users on 7/27. 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.
Tue 10/131:27 pm
MDW
- TPA
1 stop7h 17m
Delta
Sat 10/176:00 am
TPA
- MDW
1 stop7h 47m
Delta
Deal found 7/27![Delta logo]()
$229
This Southwest deal was found by Cheapflights users on 7/27. 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 8/256:00 am
MDW
- TPA
2 stops7h 05m
Southwest
Tue 9/111:35 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 7/27![Southwest logo]()
$212
This Delta deal was found by Cheapflights users on 7/27. 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.
Sat 8/296:11 am
MDW
- TPA
1 stop6h 54m
Delta
Sat 9/55:55 pm
TPA
- MDW
1 stop5h 41m
Delta
Deal found 7/27![Delta logo]()
$229
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/84:40 pm
MDW
- TPA
1 stop4h 20m
Southwest
Tue 9/1511:35 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 7/24![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:05 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Tue 9/86:45 am
TPA
- MDW
1 stop5h 50m
Southwest
Deal found 7/23![Southwest logo]()
$219
This Delta deal was found by Cheapflights users on 7/27. 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.
Sat 8/221:25 pm
MDW
- MCO
1 stop6h 40m
Delta
Tue 8/255:45 pm
MCO
- MDW
1 stop5h 51m
Delta
Deal found 7/27![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 7/26. 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 9/176:20 pm
MDW
- TPA
Nonstop2h 40m
Southwest
Mon 9/213:40 pm
TPA
- MDW
1 stop4h 55m
Southwest
Deal found 7/26![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 7/26. 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 9/97:40 am
MDW
- JAX
1 stop4h 15m
Southwest
Wed 9/161:40 pm
JAX
- MDW
2 stops6h 25m
Southwest
Deal found 7/26![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 7/26. 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 9/14:39 pm
MDW
- SRQ
1 stop5h 18m
Delta
Wed 9/96:00 am
SRQ
- MDW
1 stop5h 36m
Delta
Deal found 7/26![Delta logo]()
$288
This Southwest deal was found by Cheapflights users on 7/25. 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 9/89:00 am
MDW
- JAX
1 stop6h 45m
Southwest
Tue 9/158:00 am
JAX
- MDW
2 stops6h 05m
Southwest
Deal found 7/25![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 7/27. 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.
Sat 9/56:05 am
MDW
- PBI
1 stop6h 00m
Delta
Wed 9/96:27 pm
PBI
- MDW
1 stop5h 17m
Delta
Deal found 7/27![Delta logo]()
$293
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:45 am
MDW
- JAX
2 stops6h 45m
Southwest
Tue 9/84:40 pm
JAX
- MDW
1 stop5h 10m
Southwest
Deal found 7/23![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 7/27. 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 9/106:05 am
MDW
- PBI
1 stop4h 40m
Delta
Mon 9/144:55 pm
PBI
- MDW
1 stop6h 49m
Delta
Deal found 7/27![Delta logo]()
$293
This Southwest deal was found by Cheapflights users on 7/25. 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.
Thu 9/35:55 am
MDW
- JAX
1 stop6h 25m
Southwest
Sat 9/511:15 am
JAX
- MDW
2 stops9h 05m
Southwest
Deal found 7/25![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:05 am
MDW
- PBI
1 stop4h 43m
Delta
Mon 8/3112:22 pm
PBI
- MDW
1 stop5h 37m
Delta
Deal found 7/23![Delta logo]()
$293
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2012:05 pm
MDW
- FLL
1 stop7h 45m
Southwest
Fri 10/236:25 pm
FLL
- MDW
Nonstop3h 05m
Southwest
Deal found 7/24![Southwest logo]()
$224
This Southwest deal was found by Cheapflights users on 7/27. 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 8/256:00 am
MDW
- TPA
2 stops7h 05m
Southwest
Wed 9/237:35 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 7/27![Southwest logo]()
$224
Last-minute flights from Midway to FloridaDiscover last-minute flight deals from Midway to Florida. Data last updated July 28, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Florida. Data last updated July 28, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/27. 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 8/178:00 am
MDW
- MIA
Nonstop3h 10m
Southwest
Sat 8/227:00 am
MIA
- MDW
2 stops6h 30m
Southwest
Deal found 7/27![Southwest logo]()
$186
This Southwest deal was found by Cheapflights users on 7/27. 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 8/186:10 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Thu 8/207:10 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 7/27![Southwest logo]()
$160
This Southwest deal was found by Cheapflights users on 7/28. 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 8/196:10 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Tue 8/256:15 pm
FLL
- MDW
1 stop4h 35m
Southwest
Deal found 7/28![Southwest logo]()
$159
This Southwest deal was found by Cheapflights users on 7/27. 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 8/1912:35 pm
MDW
- FLL
2 stops6h 35m
Southwest
Wed 8/2610:55 am
FLL
- MDW
1 stop7h 40m
Southwest
Deal found 7/27![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 7/27. 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 8/206:20 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Mon 8/247:10 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 7/27![Southwest logo]()
$171
This Southwest deal was found by Cheapflights users on 7/27. 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 8/207:55 am
MDW
- MIA
1 stop7h 15m
Southwest
Mon 8/244:00 pm
MIA
- MDW
1 stop8h 45m
Southwest
Deal found 7/27![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 7/26. 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 8/203:10 pm
MDW
- MIA
2 stops5h 55m
Southwest
Sat 8/227:45 am
MIA
- MDW
1 stop9h 20m
Southwest
Deal found 7/26![Southwest logo]()
$202
This Southwest deal was found by Cheapflights users on 7/27. 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 8/2210:10 am
MDW
- FLL
1 stop4h 10m
Southwest
Tue 8/254:55 pm
FLL
- MDW
Nonstop3h 05m
Southwest
Deal found 7/27![Southwest logo]()
$166
This Southwest deal was found by Cheapflights users on 7/27. 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 8/2210:10 am
MDW
- FLL
1 stop4h 10m
Southwest
Mon 8/247:10 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 7/27![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 7/28. 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 8/258:35 am
MDW
- FLL
Nonstop3h 05m
Southwest
Tue 9/17:20 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 7/28![Southwest logo]()
$149
This Southwest deal was found by Cheapflights users on 7/28. 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 8/2712:50 pm
MDW
- MIA
2 stops6h 55m
Southwest
Sat 9/56:30 am
MIA
- MDW
1 stop5h 10m
Southwest
Deal found 7/28![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 7/26. 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.
Mon 8/317:40 am
MDW
- FLL
Nonstop2h 55m
Southwest
Sun 9/67:45 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 7/26![Southwest logo]()
$176
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 July 28, 2026.
Search for one-way flight options from Midway to Florida. Find affordable one-way fares based on user searches. Data last updated July 28, 2026.
This Southwest deal was found by Cheapflights users on 7/28. 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 9/211:10 am
MDW
- FLL
1 stop5h 35m
Southwest
Deal found 7/28![Southwest logo]()
$85
This Southwest deal was found by Cheapflights users on 7/28. 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 8/206:20 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Deal found 7/28![Southwest logo]()
$86
This Southwest deal was found by Cheapflights users on 7/27. 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 8/2210:10 am
MDW
- FLL
1 stop4h 10m
Southwest
Deal found 7/27![Southwest logo]()
$91
This Southwest deal was found by Cheapflights users on 7/27. 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 9/108:05 am
MDW
- FLL
2 stops6h 35m
Southwest
Deal found 7/27![Southwest logo]()
$96
This Southwest deal was found by Cheapflights users on 7/27. 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 9/216:45 pm
MDW
- JAX
Nonstop2h 20m
Southwest
Deal found 7/27![Southwest logo]()
$99
This Southwest deal was found by Cheapflights users on 7/26. 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 9/31:00 pm
MDW
- FLL
2 stops7h 20m
Southwest
Deal found 7/26![Southwest logo]()
$101
This Southwest deal was found by Cheapflights users on 7/27. 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 8/2712:50 pm
MDW
- MIA
2 stops6h 55m
Southwest
Deal found 7/27![Southwest logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/132:49 pm
MDW
- JAX
1 stop22h 21m
Allegiant Air
Deal found 7/24![Allegiant Air logo]()
$103
This Southwest deal was found by Cheapflights users on 7/27. 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 10/271:05 pm
MDW
- JAX
2 stops5h 35m
Southwest
Deal found 7/27![Southwest logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/132:49 pm
MDW
- MCO
1 stop28h 18m
Allegiant Air
Deal found 7/24![Allegiant Air logo]()
$104
This Southwest deal was found by Cheapflights users on 7/25. 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.
Sun 9/69:30 am
MDW
- FLL
2 stops10h 55m
Southwest
Deal found 7/25![Southwest logo]()
$106
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:10 am
MDW
- MIA
2 stops11h 20m
Southwest
Deal found 7/24![Southwest logo]()
$107
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 July 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $149 (Southwest) |
One-way from | $85 (Southwest) |
Popular in | June |
Cheapest in | September |
Average price | $315 |
Good round-trip deal | $118 or less |
Good one-way deal | $90 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 July 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 8/25
8:35 am-12:40 pm
Nonstop3h 05m
Fort Lauderdale
Sat 8/29
6:40 am-8:40 am
Nonstop3h 00m
$160
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Wed 8/19
8:15 am-1:55 pm
1 stop4h 40m
Fort Lauderdale
Wed 8/26
7:20 am-9:20 am
Nonstop3h 00m
$181
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Sun 9/6
9:30 am-9:25 pm
2 stops10h 55m
Fort Lauderdale
Thu 9/10
7:10 am-9:10 am
Nonstop3h 00m
$191
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Thu 9/10
8:05 am-3:40 pm
2 stops6h 35m
Fort Lauderdale
Thu 9/24
6:35 pm-10:25 pm
1 stop4h 50m
$192
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Thu 8/27
6:20 am-1:40 pm
1 stop6h 20m
Fort Lauderdale
Mon 8/31
7:00 am-12:25 pm
2 stops6h 25m
$196
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Thu 9/10
3:10 pm-10:10 pm
2 stops6h 00m
Miami
Mon 9/14
7:15 am-9:20 am
Nonstop3h 05m
$196
Quickest round-trip
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Thu 8/27
12:10 pm-3:45 pm
Nonstop2h 35m
Tampa
Wed 9/2
11:35 am-1:15 pm
Nonstop2h 40m
$209
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Tue 8/25
6:00 am-2:05 pm
2 stops7h 05m
Tampa
Tue 9/1
11:35 am-1:15 pm
Nonstop2h 40m
$212
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Sat 10/10
11:33 am-7:39 pm
1 stop7h 06m
Fort Lauderdale
Tue 10/13
12:09 pm-4:19 pm
1 stop5h 10m
$217
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Sat 9/26
4:30 pm-12:40 am
1 stop7h 10m
Fort Lauderdale
Tue 9/29
9:59 am-4:15 pm
1 stop7h 16m
$217
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-JAX
MDW-MIA
MDW-MCO
MDW-TPA
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-JAX
MDW-MIA
MDW-MCO
What is the cheapest month to book a flight from Chicago Midway Airport to Florida?
Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Florida (average of $247). Flying from Chicago Midway Airport to Florida in June is currently the most expensive (average of $408). 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 July 28, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 14% on flights from Chicago Midway Airport to Florida by exploring options for tickets at noon.
How much does it cost to fly round-trip from Chicago Midway Airport to Florida?
Airfare is below average for this route at the moment.
Chicago Midway Airport to Florida flights typically cost between $267 and $383 in September.The cheapest round-trip price found within the last 5 days was $186 on Southwest (Sep 10-Sep 14).
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 86 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 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 July 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. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 July 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.
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
Find useful and relevant information for your journey from Midway to 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 July 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 4 airlines flying from Midway to Florida
Discover the top 4 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 July 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$59 | Average$214 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$134 | Average$324 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$173 | Average$388 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$203 | Average$395 | FlexibilityNo cancel fee | On-time71% |