$82+ 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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MIA
Jul 12 — Jul 191
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 June 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 June 12, 2026.
This Southwest deal was found by Cheapflights users on 6/8. 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 8/258:35 am
MDW
- FLL
Nonstop3h 05m
Southwest
Tue 9/17:20 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 6/8![Southwest logo]()
$163
This Southwest deal was found by Cheapflights users on 6/12. 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.
Tue 9/158:35 am
MDW
- FLL
Nonstop3h 05m
Southwest
Tue 9/224:55 pm
FLL
- MDW
Nonstop3h 05m
Southwest
Deal found 6/12![Southwest logo]()
$171
This Southwest deal was found by Cheapflights users on 6/8. 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 8/1111:10 am
MDW
- FLL
1 stop7h 25m
Southwest
Tue 8/184:55 pm
FLL
- MDW
Nonstop3h 05m
Southwest
Deal found 6/8![Southwest logo]()
$173
This Southwest deal was found by Cheapflights users on 6/11. 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 8/156:15 am
MDW
- FLL
Nonstop2h 50m
Southwest
Tue 8/184:55 pm
FLL
- MDW
Nonstop3h 05m
Southwest
Deal found 6/11![Southwest logo]()
$180
This Southwest deal was found by Cheapflights users on 6/12. 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.
Tue 7/287:40 am
MDW
- FLL
Nonstop3h 00m
Southwest
Tue 8/46:35 pm
FLL
- MDW
1 stop4h 45m
Southwest
Deal found 6/12![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 6/11. 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 9/18:15 am
MDW
- FLL
1 stop4h 40m
Southwest
Tue 9/86:35 pm
FLL
- MDW
1 stop4h 45m
Southwest
Deal found 6/11![Southwest logo]()
$183
This Southwest deal was found by Cheapflights users on 6/12. 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.
Tue 8/186:10 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Sat 8/226:40 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 6/12![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 6/12. 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.
Tue 7/146:55 pm
MDW
- FLL
Nonstop3h 00m
Southwest
Tue 7/217:00 am
FLL
- MDW
Nonstop3h 05m
Southwest
Deal found 6/12![Southwest logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Tue 9/86:00 am
MDW
- TPA
1 stop11h 51m
Frontier
Tue 9/157:00 am
TPA
- MDW
1 stop4h 58m
Frontier
Deal found 6/10![Frontier logo]()
$191
This Southwest deal was found by Cheapflights users on 6/8. 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 8/2512:20 pm
MDW
- MCO
Nonstop2h 40m
Southwest
Tue 9/11:00 pm
MCO
- MDW
Nonstop2h 45m
Southwest
Deal found 6/8![Southwest logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Wed 8/1912:04 pm
MDW
- TPA
1 stop5h 47m
Frontier
Tue 8/254:46 pm
TPA
- MDW
1 stop6h 25m
Frontier
Deal found 6/11![Frontier logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 6/10. 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
Tue 8/185:31 am
MCO
- MDW
1 stop6h 41m
Frontier
Deal found 6/10![Frontier logo]()
$194
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 June 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 June 12, 2026.
This Southwest deal was found by Cheapflights users on 6/10. 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.
Tue 8/1112:35 pm
MDW
- FLL
2 stops6h 35m
Southwest
Tue 8/187:20 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 6/10![Southwest logo]()
$178
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/261:00 pm
MDW
- FLL
1 stop6h 57m
Delta
Wed 12/25:30 am
FLL
- MDW
1 stop5h 22m
Delta
Deal found 6/12![Delta logo]()
$220
This Southwest deal was found by Cheapflights users on 6/11. 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 8/296:15 am
MDW
- FLL
Nonstop2h 50m
Southwest
Sat 9/56:40 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 6/11![Southwest logo]()
$196
This Southwest deal was found by Cheapflights users on 6/8. 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 10/206:00 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Mon 10/266:45 pm
FLL
- MDW
1 stop5h 05m
Southwest
Deal found 6/8![Southwest logo]()
$199
This Delta deal was found by Cheapflights users on 6/11. 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.
Thu 9/175:10 pm
MDW
- FLL
1 stop5h 19m
Delta
Sun 9/206:00 am
FLL
- MDW
1 stop7h 34m
Delta
Deal found 6/11![Delta logo]()
$222
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/261:00 pm
MDW
- FLL
1 stop6h 57m
Delta
Thu 12/36:10 pm
FLL
- MDW
1 stop5h 00m
Delta
Deal found 6/12![Delta logo]()
$223
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/28:10 am
MDW
- MCO
1 stop4h 50m
Southwest
Tue 12/83:50 pm
MCO
- MDW
1 stop4h 50m
Southwest
Deal found 6/9![Southwest logo]()
$206
This Delta deal was found by Cheapflights users on 6/8. 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.
Tue 9/110:54 am
MDW
- MIA
1 stop6h 48m
Delta
Tue 9/84:40 pm
MIA
- MDW
1 stop6h 06m
Delta
Deal found 6/8![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 6/12. 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.
Tue 7/288:10 am
MDW
- FLL
1 stop7h 10m
Southwest
Tue 8/46:35 pm
FLL
- MDW
1 stop4h 45m
Southwest
Deal found 6/12![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 6/8. 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.
Wed 7/156:55 pm
MDW
- FLL
Nonstop3h 00m
Southwest
Sat 7/1810:25 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 6/8![Southwest logo]()
$212
This Delta deal was found by Cheapflights users on 6/8. 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.
Sat 8/296:05 am
MDW
- MCO
1 stop5h 54m
Delta
Sat 9/510:05 am
MCO
- MDW
1 stop6h 39m
Delta
Deal found 6/8![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 6/8. 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 8/117:40 am
MDW
- MCO
2 stops5h 55m
Southwest
Wed 8/128:45 am
MCO
- MDW
1 stop6h 10m
Southwest
Deal found 6/8![Southwest logo]()
$216
This Delta deal was found by Cheapflights users on 6/8. 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.
Wed 8/1212:46 pm
MDW
- JAX
1 stop4h 08m
Delta
Mon 8/175:34 pm
JAX
- MDW
1 stop6h 02m
Delta
Deal found 6/8![Delta logo]()
$260
This Southwest deal was found by Cheapflights users on 6/8. 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.
Wed 7/87:50 am
MDW
- FLL
1 stop8h 05m
Southwest
Sat 7/117:00 am
FLL
- MDW
Nonstop3h 05m
Southwest
Deal found 6/8![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 6/9. 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.
Fri 9/256:20 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Mon 9/284:15 pm
FLL
- MDW
1 stop4h 30m
Southwest
Deal found 6/9![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 6/11. 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 7/92:45 pm
MDW
- FLL
1 stop7h 55m
Southwest
Sun 7/126:10 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 6/11![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1810:54 am
MDW
- PBI
1 stop6h 40m
Delta
Sat 8/226:27 pm
PBI
- MDW
1 stop5h 09m
Delta
Deal found 6/12![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 6/11. 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.
Sat 7/116:00 am
MDW
- PBI
1 stop5h 54m
Delta
Sat 7/184:55 pm
PBI
- MDW
1 stop6h 20m
Delta
Deal found 6/11![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 6/8. 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.
Mon 9/217:50 pm
MDW
- MCO
Nonstop2h 30m
Southwest
Wed 9/238:45 am
MCO
- MDW
1 stop6h 10m
Southwest
Deal found 6/8![Southwest logo]()
$236
This Delta deal was found by Cheapflights users on 6/10. 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.
Wed 7/16:00 am
MDW
- PBI
1 stop4h 46m
Delta
Sat 7/42:03 pm
PBI
- MDW
1 stop6h 59m
Delta
Deal found 6/10![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 6/10. 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 7/811:45 am
MDW
- MIA
Nonstop3h 00m
Southwest
Wed 7/154:00 pm
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 6/10![Southwest logo]()
$239
This Delta deal was found by Cheapflights users on 6/8. 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.
Tue 8/1110:54 am
MDW
- PBI
1 stop6h 40m
Delta
Wed 8/198:00 am
PBI
- MDW
1 stop4h 51m
Delta
Deal found 6/8![Delta logo]()
$311
This Southwest deal was found by Cheapflights users on 6/8. 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.
Wed 7/17:50 am
MDW
- JAX
2 stops8h 05m
Southwest
Tue 7/1411:05 am
JAX
- MDW
1 stop7h 50m
Southwest
Deal found 6/8![Southwest logo]()
$242
This Delta deal was found by Cheapflights users on 6/7. 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.
Wed 7/225:10 pm
MDW
- RSW
1 stop6h 13m
Delta
Sat 7/256:27 pm
RSW
- MDW
1 stop4h 48m
Delta
Deal found 6/7![Delta logo]()
$315
This Southwest deal was found by Cheapflights users on 6/8. 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.
Wed 8/57:40 am
MDW
- TPA
2 stops6h 10m
Southwest
Wed 8/123:00 pm
TPA
- MDW
1 stop5h 35m
Southwest
Deal found 6/8![Southwest logo]()
$246
This Delta deal was found by Cheapflights users on 6/8. 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.
Sat 7/116:00 am
MDW
- PBI
1 stop4h 48m
Delta
Mon 7/1311:02 am
PBI
- MDW
1 stop6h 13m
Delta
Deal found 6/8![Delta logo]()
$315
This Southwest deal was found by Cheapflights users on 6/10. 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.
Tue 7/77:50 am
MDW
- JAX
2 stops8h 05m
Southwest
Wed 7/152:55 pm
JAX
- MDW
2 stops8h 05m
Southwest
Deal found 6/10![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 6/9. 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.
Tue 8/116:05 am
MDW
- ECP
1 stop6h 43m
Delta
Sun 8/166:00 am
ECP
- MDW
1 stop5h 51m
Delta
Deal found 6/9![Delta logo]()
$330
This Southwest deal was found by Cheapflights users on 6/9. 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 10/178:05 am
MDW
- MCO
1 stop5h 10m
Southwest
Mon 10/197:55 am
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 6/9![Southwest logo]()
$252
This Delta deal was found by Cheapflights users on 6/11. 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 8/125:10 pm
MDW
- ECP
1 stop4h 30m
Delta
Sun 8/166:00 am
ECP
- MDW
1 stop3h 59m
Delta
Deal found 6/11![Delta logo]()
$331
Last-minute flights from Midway to FloridaDiscover last-minute flight deals from Midway to Florida. Data last updated June 12, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Florida. Data last updated June 12, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/9. 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 6/308:10 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Wed 9/27:35 am
MCO
- MDW
Nonstop2h 45m
Southwest
Deal found 6/9![Southwest logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Fri 7/33:28 pm
MDW
- FLL
1 stop16h 00m
Allegiant Air
Sun 7/128:34 pm
FLL
- MDW
1 stop19h 04m
Allegiant Air
Deal found 6/9![Allegiant Air logo]()
$200
This Southwest deal was found by Cheapflights users on 6/9. 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 7/412:45 pm
MDW
- FLL
Nonstop3h 00m
Southwest
Wed 7/87:00 am
FLL
- MDW
Nonstop3h 05m
Southwest
Deal found 6/9![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 6/12. 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.
Sat 7/47:35 am
MDW
- FLL
1 stop8h 50m
Southwest
Tue 7/77:25 pm
FLL
- MDW
1 stop4h 50m
Southwest
Deal found 6/12![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/85:25 am
MDW
- TPA
Nonstop2h 30m
Southwest
Wed 7/229:55 pm
TPA
- MDW
Nonstop2h 45m
Southwest
Deal found 6/9![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 6/8. 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.
Wed 7/88:10 pm
MDW
- MCO
Nonstop2h 40m
Southwest
Wed 7/157:10 am
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 6/8![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 6/12. 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.
Tue 7/146:55 pm
MDW
- FLL
Nonstop3h 00m
Southwest
Tue 7/217:00 am
FLL
- MDW
Nonstop3h 05m
Southwest
Deal found 6/12![Southwest logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Thu 7/162:48 pm
MDW
- FLL
1 stop7h 25m
Allegiant Air
Sun 7/198:34 pm
FLL
- MDW
1 stop19h 04m
Allegiant Air
Deal found 6/9![Allegiant Air logo]()
$194
This Southwest deal was found by Cheapflights users on 6/12. 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.
Tue 7/287:40 am
MDW
- FLL
Nonstop3h 00m
Southwest
Tue 8/46:35 pm
FLL
- MDW
1 stop4h 45m
Southwest
Deal found 6/12![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 6/9. 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 7/287:40 am
MDW
- FLL
Nonstop3h 00m
Southwest
Tue 8/112:55 pm
FLL
- MDW
1 stop6h 50m
Southwest
Deal found 6/9![Southwest logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Tue 7/286:05 am
MDW
- TPA
1 stop11h 47m
Frontier
Wed 8/55:40 pm
TPA
- MDW
1 stop5h 23m
Frontier
Deal found 6/10![Frontier logo]()
$207
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:55 pm
MDW
- FLL
Nonstop3h 00m
Southwest
Thu 8/137:10 am
FLL
- MDW
Nonstop3h 00m
Southwest
Deal found 6/9![Southwest logo]()
$211
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 June 12, 2026.
Search for one-way flight options from Midway to Florida. Find affordable one-way fares based on user searches. Data last updated June 12, 2026.
This Southwest deal was found by Cheapflights users on 6/10. 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.
Tue 9/86:10 pm
MDW
- FLL
Nonstop2h 55m
Southwest
Deal found 6/10![Southwest logo]()
$82
This Southwest deal was found by Cheapflights users on 6/12. 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.
Tue 7/146:55 pm
MDW
- FLL
Nonstop3h 00m
Southwest
Deal found 6/12![Southwest logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 6/12. 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.
Thu 7/92:48 pm
MDW
- JAX
1 stop22h 12m
Allegiant Air
Deal found 6/12![Allegiant Air logo]()
$90
This Trip.com deal was found by Cheapflights users on 6/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:05 am
MDW
- JAX
1 stop10h 29m
Frontier
Deal found 6/10![Frontier logo]()
$92
This Trip.com deal was found by Cheapflights users on 6/9. 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.
Tue 8/186:00 am
MDW
- JAX
1 stop10h 37m
Frontier
Deal found 6/9![Frontier logo]()
$94
This Trip.com deal was found by Cheapflights users on 6/11. 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.
Wed 8/1211:06 am
MDW
- MCO
1 stop10h 09m
Frontier
Deal found 6/11![Frontier logo]()
$94
This Trip.com deal was found by Cheapflights users on 6/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:05 am
MDW
- MCO
1 stop11h 28m
Frontier
Deal found 6/10![Frontier logo]()
$95
This Southwest deal was found by Cheapflights users on 6/11. 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 12/86:20 pm
MDW
- FLL
Nonstop3h 00m
Southwest
Deal found 6/11![Southwest logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 7/226:05 am
MDW
- JAX
1 stop10h 29m
Frontier
Deal found 6/10![Frontier logo]()
$96
This Southwest deal was found by Cheapflights users on 6/8. 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.
Wed 8/193:30 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Deal found 6/8![Southwest logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Tue 7/76:05 am
MDW
- JAX
1 stop10h 29m
Frontier
Deal found 6/10![Frontier logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Tue 9/86:00 am
MDW
- MCO
1 stop15h 09m
Frontier
Deal found 6/10![Frontier logo]()
$97
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 June 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $163 (Southwest) |
One-way from | $82 (Southwest) |
Popular in | June |
Cheapest in | August |
Average price | $330 |
Good round-trip deal | $126 or less |
Good one-way deal | $50 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 June 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
Tue 8/11
12:35 pm-8:10 pm
2 stops6h 35m
Fort Lauderdale
Tue 8/18
7:20 am-9:20 am
Nonstop3h 00m
$178
Quickest round-trip
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Sat 8/29
6:15 am-10:05 am
Nonstop2h 50m
Fort Lauderdale
Sat 9/5
6:40 am-8:40 am
Nonstop3h 00m
$196
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Tue 10/20
6:00 pm-9:55 pm
Nonstop2h 55m
Fort Lauderdale
Mon 10/26
6:45 pm-10:50 pm
1 stop5h 05m
$199
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Wed 12/2
8:10 am-2:00 pm
1 stop4h 50m
Orlando
Tue 12/8
3:50 pm-7:40 pm
1 stop4h 50m
$206
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Tue 7/28
8:10 am-4:20 pm
1 stop7h 10m
Fort Lauderdale
Tue 8/4
6:35 pm-10:20 pm
1 stop4h 45m
$209
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Wed 7/15
6:55 pm-10:55 pm
Nonstop3h 00m
Fort Lauderdale
Sat 7/18
10:25 am-12:25 pm
Nonstop3h 00m
$212
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Tue 8/11
7:40 am-2:35 pm
2 stops5h 55m
Orlando
Wed 8/12
8:45 am-1:55 pm
1 stop6h 10m
$216
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Thu 11/26
1:00 pm-8:57 pm
1 stop6h 57m
Fort Lauderdale
Wed 12/2
5:30 am-9:52 am
1 stop5h 22m
$220
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Thu 9/17
5:10 pm-11:29 pm
1 stop5h 19m
Fort Lauderdale
Sun 9/20
6:00 am-12:34 pm
1 stop7h 34m
$222
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Wed 7/8
7:50 am-4:55 pm
1 stop8h 05m
Fort Lauderdale
Sat 7/11
7:00 am-9:05 am
Nonstop3h 05m
$222
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-MCO
MDW-MIA
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-FLL
MDW-JAX
MDW-MCO
MDW-MIA
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 $729). 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 June 12, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 9% 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 June 8, 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 June 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.
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
7.9
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
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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 June 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 June 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$58 | Average$192 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$134 | Average$320 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$171 | Average$377 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$203 | Average$395 | FlexibilityNo cancel fee | On-time71% |