$81+ 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 8/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MIA
Aug 11 — Aug 181
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 12, 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 12, 2026.
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/247:40 am
MDW
- FLL
Nonstop2h 55m
Southwest
Mon 8/317:10 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 7/10![Southwest logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:17 pm
MDW
- FLL
1 stop14h 46m
Frontier
Thu 8/2010:58 am
FLL
- MDW
1 stop10h 33m
Frontier
Deal found 7/9![Frontier logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/249:26 pm
MDW
- FLL
1 stop11h 37m
Frontier
Mon 8/313:00 pm
FLL
- MDW
1 stop8h 47m
Frontier
Deal found 7/10![Frontier logo]()
$175
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 9/193:20 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Thu 9/245:40 pm
FLL
- MDW
Nonstop3h 10m
Southwest
Deal found 7/10![Southwest logo]()
$176
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 11/97:30 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Thu 11/126:00 am
FLL
- MDW
1 stop5h 25m
Southwest
Deal found 7/10![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:20 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Thu 8/277:10 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 7/7![Southwest logo]()
$179
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:10 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Thu 9/1011:05 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 7/9![Southwest logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/143:49 pm
MDW
- FLL
1 stop16h 09m
Allegiant Air
Sun 8/168:36 pm
FLL
- MDW
1 stop19h 23m
Allegiant Air
Deal found 7/12![Allegiant Air logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1011:06 am
MDW
- MCO
1 stop7h 51m
Frontier
Mon 8/1710:00 am
MCO
- MDW
1 stop25h 55m
Frontier
Deal found 7/11![Frontier logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/412:11 pm
MDW
- MCO
1 stop9h 04m
Frontier
Sat 8/83:18 pm
MCO
- MDW
1 stop7h 45m
Frontier
Deal found 7/11![Frontier logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1311:06 am
MDW
- FLL
1 stop12h 36m
Multiple Airlines
Sun 8/168:36 pm
FLL
- MDW
1 stop19h 23m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1511:06 am
MDW
- MCO
1 stop10h 09m
Frontier
Sat 8/225:23 pm
MCO
- MDW
1 stop6h 24m
Frontier
Deal found 7/11![Frontier logo]()
$184
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 12, 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 12, 2026.
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:15 am
MDW
- FLL
Nonstop2h 50m
Southwest
Thu 9/175:40 pm
FLL
- MDW
Nonstop3h 10m
Southwest
Deal found 7/11![Southwest logo]()
$171
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/2012:46 pm
MDW
- FLL
1 stop5h 57m
Delta
Mon 8/245:30 am
FLL
- MDW
1 stop7h 21m
Delta
Deal found 7/10![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:20 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Mon 8/247:10 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 7/9![Southwest logo]()
$179
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1010:30 am
MDW
- FLL
1 stop5h 35m
Southwest
Tue 9/154:55 pm
FLL
- MDW
Nonstop3h 05m
Southwest
Deal found 7/11![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/259:25 am
MDW
- FLL
1 stop5h 20m
Southwest
Sat 8/296:40 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 7/11![Southwest logo]()
$181
This Delta deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:35 am
MDW
- MIA
1 stop6h 31m
Delta
Mon 9/141:12 pm
MIA
- MDW
1 stop6h 21m
Delta
Deal found 7/7![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:35 pm
MDW
- FLL
2 stops6h 35m
Southwest
Wed 9/24:55 pm
FLL
- MDW
Nonstop3h 05m
Southwest
Deal found 7/11![Southwest logo]()
$186
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 7/10![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 10/2211:00 am
MDW
- FLL
1 stop7h 45m
Southwest
Tue 11/36:45 am
FLL
- MDW
Nonstop3h 05m
Southwest
Deal found 7/10![Southwest logo]()
$189
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 9/196:05 am
MDW
- JAX
1 stop4h 52m
Delta
Tue 9/226:59 pm
JAX
- MDW
1 stop4h 46m
Delta
Deal found 7/10![Delta logo]()
$235
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/264:15 pm
MDW
- FLL
1 stop5h 45m
Southwest
Thu 10/296:25 pm
FLL
- MDW
Nonstop3h 05m
Southwest
Deal found 7/9![Southwest logo]()
$190
This Delta deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:56 am
MDW
- JAX
1 stop5h 49m
Delta
Sat 9/125:34 pm
JAX
- MDW
1 stop6h 11m
Delta
Deal found 7/7![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:55 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Sat 10/316:40 am
FLL
- MDW
1 stop5h 00m
Southwest
Deal found 7/7![Southwest logo]()
$190
This Delta deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:11 am
MDW
- TPA
1 stop5h 28m
Delta
Tue 8/187:30 am
TPA
- MDW
1 stop5h 21m
Delta
Deal found 7/9![Delta logo]()
$241
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/35:25 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Sat 10/106:20 am
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 7/9![Southwest logo]()
$190
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:05 am
MDW
- SRQ
1 stop5h 50m
Delta
Tue 9/85:40 pm
SRQ
- MDW
1 stop6h 05m
Delta
Deal found 7/8![Delta logo]()
$252
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/199:40 am
MDW
- MCO
Nonstop2h 35m
Southwest
Mon 8/247:10 am
MCO
- MDW
1 stop5h 15m
Southwest
Deal found 7/10![Southwest logo]()
$195
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/95:15 pm
MDW
- MIA
1 stop6h 38m
Delta
Sat 10/178:00 am
MIA
- MDW
1 stop5h 48m
Delta
Deal found 7/8![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:15 am
MDW
- MCO
Nonstop2h 30m
Southwest
Wed 8/129:00 am
MCO
- MDW
1 stop4h 05m
Southwest
Deal found 7/7![Southwest logo]()
$196
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/79:29 am
MDW
- MCO
1 stop4h 24m
Delta
Mon 10/126:00 am
MCO
- MDW
1 stop7h 48m
Delta
Deal found 7/11![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/258:10 am
MDW
- FLL
Nonstop2h 55m
Southwest
Tue 10/276:50 am
FLL
- MDW
Nonstop3h 10m
Southwest
Deal found 7/11![Southwest logo]()
$204
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:10 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Fri 8/147:10 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 7/8![Southwest logo]()
$205
This KAYAK deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:05 am
MDW
- MCO
1 stop5h 55m
Delta
Tue 9/112:05 pm
MCO
- MDW
1 stop4h 39m
Delta
Deal found 7/8![Delta logo]()
$275
This Southwest deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:05 am
MDW
- TPA
Nonstop2h 30m
Southwest
Mon 9/76:20 am
TPA
- MDW
1 stop6h 55m
Southwest
Deal found 7/7![Southwest logo]()
$208
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:11 pm
MDW
- JAX
1 stop4h 32m
Delta
Mon 9/216:00 am
JAX
- MDW
1 stop6h 55m
Delta
Deal found 7/11![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:40 am
MDW
- MCO
2 stops6h 30m
Southwest
Thu 9/36:20 pm
MCO
- MDW
1 stop4h 35m
Southwest
Deal found 7/9![Southwest logo]()
$215
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1910:54 am
MDW
- RSW
1 stop4h 50m
Delta
Wed 8/266:29 pm
RSW
- MDW
1 stop5h 07m
Delta
Deal found 7/11![Delta logo]()
$295
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/67:55 pm
MDW
- TPA
Nonstop2h 30m
Southwest
Mon 8/107:05 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 7/12![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/315:10 pm
MDW
- PBI
1 stop6h 41m
Delta
Mon 8/36:27 pm
PBI
- MDW
1 stop5h 09m
Delta
Deal found 7/8![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:55 pm
MDW
- TPA
Nonstop2h 30m
Southwest
Mon 9/75:15 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 7/8![Southwest logo]()
$221
Last-minute flights from Midway to FloridaDiscover last-minute flight deals from Midway to Florida. Data last updated July 12, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Florida. Data last updated July 12, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/412:11 pm
MDW
- MCO
1 stop9h 04m
Frontier
Mon 8/105:24 pm
MCO
- MDW
1 stop5h 39m
Frontier
Deal found 7/11![Frontier logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/412:11 pm
MDW
- MCO
1 stop9h 04m
Frontier
Sat 8/83:18 pm
MCO
- MDW
1 stop7h 45m
Frontier
Deal found 7/9![Frontier logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/66:05 am
MDW
- FLL
1 stop6h 55m
Frontier
Sun 8/96:05 am
FLL
- MDW
1 stop16h 58m
Frontier
Deal found 7/10![Frontier logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1011:06 am
MDW
- MCO
1 stop7h 51m
Frontier
Mon 8/1710:00 am
MCO
- MDW
1 stop25h 55m
Frontier
Deal found 7/11![Frontier logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1211:06 am
MDW
- MCO
1 stop6h 27m
Frontier
Sun 8/167:45 am
MCO
- MDW
1 stop15h 18m
Frontier
Deal found 7/10![Frontier logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1311:06 am
MDW
- FLL
1 stop12h 36m
Multiple Airlines
Sun 8/168:36 pm
FLL
- MDW
1 stop19h 23m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/143:49 pm
MDW
- FLL
1 stop16h 09m
Allegiant Air
Sun 8/168:36 pm
FLL
- MDW
1 stop19h 23m
Allegiant Air
Deal found 7/11![Allegiant Air logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1511:06 am
MDW
- MCO
1 stop10h 09m
Frontier
Sat 8/225:23 pm
MCO
- MDW
1 stop6h 24m
Frontier
Deal found 7/11![Frontier logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:17 pm
MDW
- FLL
1 stop14h 46m
Frontier
Thu 8/2010:58 am
FLL
- MDW
1 stop10h 33m
Frontier
Deal found 7/9![Frontier logo]()
$174
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 7/10![Southwest logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/249:26 pm
MDW
- FLL
1 stop11h 37m
Frontier
Mon 8/313:00 pm
FLL
- MDW
1 stop8h 47m
Frontier
Deal found 7/10![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/249:26 pm
MDW
- FLL
1 stop11h 37m
Frontier
Thu 8/273:00 pm
FLL
- MDW
1 stop8h 47m
Frontier
Deal found 7/9![Frontier logo]()
$180
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 12, 2026.
Search for one-way flight options from Midway to Florida. Find affordable one-way fares based on user searches. Data last updated July 12, 2026.
This Trip.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/711:06 am
MDW
- JAX
1 stop5h 28m
Frontier
Deal found 7/9![Frontier logo]()
$81
This Trip.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:05 am
MDW
- JAX
1 stop10h 29m
Frontier
Deal found 7/8![Frontier logo]()
$82
This Trip.com deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:05 am
MDW
- JAX
1 stop10h 29m
Frontier
Deal found 7/7![Frontier logo]()
$83
This Kiwi.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:05 am
MDW
- JAX
1 stop10h 29m
Frontier
Deal found 7/9![Frontier logo]()
$85
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:20 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Deal found 7/12![Southwest logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:05 am
MDW
- JAX
1 stop11h 05m
Frontier
Deal found 7/7![Frontier logo]()
$88
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:20 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Deal found 7/8![Southwest logo]()
$90
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/136:20 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Deal found 7/10![Southwest logo]()
$91
This Trip.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:40 am
MDW
- FLL
1 stop15h 29m
Frontier
Deal found 7/8![Frontier logo]()
$92
This Trip.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2911:45 am
MDW
- JAX
1 stop5h 25m
Frontier
Deal found 7/11![Frontier logo]()
$92
This Trip.com deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/412:11 pm
MDW
- MCO
1 stop9h 04m
Frontier
Deal found 7/7![Frontier logo]()
$92
This Trip.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/236:05 am
MDW
- JAX
1 stop11h 05m
Frontier
Deal found 7/8![Frontier logo]()
$93
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 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $171 (Southwest) |
One-way from | $81 (Trip.com) |
Popular in | June |
Cheapest in | September |
Average price | $273 |
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 12, 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
Sat 9/12
6:15 am-10:05 am
Nonstop2h 50m
Fort Lauderdale
Thu 9/17
5:40 pm-7:50 pm
Nonstop3h 10m
$171
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Thu 8/20
6:20 pm-10:15 pm
Nonstop2h 55m
Fort Lauderdale
Mon 8/24
7:10 am-9:10 am
Nonstop3h 00m
$179
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Thu 9/10
10:30 am-5:05 pm
1 stop5h 35m
Fort Lauderdale
Tue 9/15
4:55 pm-7:00 pm
Nonstop3h 05m
$181
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Tue 8/25
9:25 am-3:45 pm
1 stop5h 20m
Fort Lauderdale
Sat 8/29
6:40 am-8:40 am
Nonstop3h 00m
$181
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Wed 8/26
12:35 pm-8:10 pm
2 stops6h 35m
Fort Lauderdale
Wed 9/2
4:55 pm-7:00 pm
Nonstop3h 05m
$186
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Thu 10/22
11:00 am-7:45 pm
1 stop7h 45m
Fort Lauderdale
Tue 11/3
6:45 am-8:50 am
Nonstop3h 05m
$189
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Mon 10/26
4:15 pm-11:00 pm
1 stop5h 45m
Fort Lauderdale
Thu 10/29
6:25 pm-8:30 pm
Nonstop3h 05m
$190
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Tue 10/20
5:55 pm-9:50 pm
Nonstop2h 55m
Fort Lauderdale
Sat 10/31
6:40 am-10:40 am
1 stop5h 00m
$190
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Sat 10/3
5:25 pm-9:00 pm
Nonstop2h 35m
Orlando
Sat 10/10
6:20 am-8:10 am
Nonstop2h 50m
$190
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Wed 8/19
9:40 am-1:15 pm
Nonstop2h 35m
Orlando
Mon 8/24
7:10 am-11:25 am
1 stop5h 15m
$195
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-JAX
MDW-FLL
MDW-MCO
MDW-EYW
MDW-PBI
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-JAX
MDW-FLL
MDW-MCO
MDW-EYW
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 $723). 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 12, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 15% 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?
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 11, 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 12, 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.
Comfort
8.0
Overall
7.9
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
7.9
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
7.9
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
7.9
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
7.9
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
7.9
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
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
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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 12, 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 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$59 | Average$217 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$134 | Average$321 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$173 | Average$385 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$203 | Average$395 | FlexibilityNo cancel fee | On-time71% |