$81+ Cheap flights from Midway (MDW) to Florida Keys
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
Jun 24 — Jul 11
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Midway to Florida Keys with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midway to Florida Keys
Cheapest
Best
Last-minute
One-way
Cheapest flights from Midway to Florida KeysExplore the most affordable flight options available from Midway to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 25, 2026.
Explore the most affordable flight options available from Midway to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 25, 2026.
This Southwest deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 9/169:25 am
MDW
- MIA
Nonstop3h 00m
Southwest
Wed 9/234:00 pm
MIA
- MDW
Nonstop3h 05m
Southwest
Deal found 5/21![Southwest logo]()
$201
This Southwest deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/711:45 am
MDW
- MIA
Nonstop3h 00m
Southwest
Tue 7/144:00 pm
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 5/25![Southwest logo]()
$219
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:00 am
MDW
- MIA
1 stop6h 02m
Delta
Tue 7/146:00 am
MIA
- MDW
1 stop5h 05m
Delta
Deal found 5/22![Delta logo]()
$221
This Southwest deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 9/107:25 am
MDW
- MIA
1 stop6h 55m
Southwest
Wed 9/164:00 pm
MIA
- MDW
Nonstop3h 05m
Southwest
Deal found 5/22![Southwest logo]()
$223
This Frontier deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:05 am
MDW
- MIA
1 stop6h 48m
Frontier
Wed 7/1511:19 am
MIA
- MDW
1 stop11h 44m
Frontier
Deal found 5/24![Frontier logo]()
$230
This Frontier deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:00 am
MDW
- MIA
1 stop6h 49m
Frontier
Wed 7/155:28 pm
MIA
- MDW
1 stop5h 35m
Frontier
Deal found 5/24![Frontier logo]()
$231
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 7/810:00 am
MDW
- MIA
1 stop5h 25m
Southwest
Tue 7/1411:45 am
MIA
- MDW
1 stop5h 10m
Southwest
Deal found 5/20![Southwest logo]()
$234
This Orbitz deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/612:11 pm
MDW
- MIA
1 stop9h 54m
Frontier
Tue 8/115:28 pm
MIA
- MDW
1 stop5h 35m
Frontier
Deal found 5/21![Frontier logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/232:48 pm
MDW
- EYW
1 stop17h 53m
Allegiant Air
Sun 7/2610:55 am
EYW
- MDW
1 stop28h 43m
Allegiant Air
Deal found 5/23![Allegiant Air logo]()
$328
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 8/1312:46 pm
MDW
- EYW
1 stop6h 08m
Delta
Tue 8/187:40 am
EYW
- MDW
1 stop5h 11m
Delta
Deal found 5/20![Delta logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/282:46 pm
MDW
- EYW
1 stop17h 55m
Multiple Airlines
Thu 7/212:05 pm
EYW
- MDW
2 stops11h 06m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$350
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 12/51:05 pm
MDW
- EYW
1 stop5h 38m
Delta
Thu 12/106:00 pm
EYW
- MDW
1 stop4h 45m
Delta
Deal found 5/20![Delta logo]()
$354
Best flights from Midway to Florida KeysDiscover carefully curated flight deals from Midway to Florida Keys that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 25, 2026.
Discover carefully curated flight deals from Midway to Florida Keys that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 25, 2026.
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 8/42:40 pm
MDW
- MIA
1 stop4h 30m
Southwest
Wed 12/169:30 am
MIA
- MDW
2 stops8h 40m
Southwest
Deal found 5/20![Southwest logo]()
$293
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 8/1312:46 pm
MDW
- EYW
1 stop6h 08m
Delta
Tue 8/187:40 am
EYW
- MDW
1 stop5h 11m
Delta
Deal found 5/20![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 8/1410:54 am
MDW
- EYW
1 stop5h 26m
Delta
Tue 8/187:40 am
EYW
- MDW
1 stop5h 11m
Delta
Deal found 5/21![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 7/711:45 am
MDW
- MIA
Nonstop3h 00m
Southwest
Sat 7/118:45 pm
MIA
- MDW
1 stop11h 25m
Southwest
Deal found 5/22![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/198:00 am
MDW
- MIA
Nonstop3h 00m
Southwest
Tue 6/234:20 pm
MIA
- MDW
1 stop5h 50m
Southwest
Deal found 5/23![Southwest logo]()
$364
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 8/137:25 am
MDW
- MIA
1 stop6h 55m
Southwest
Sun 8/166:45 am
MIA
- MDW
2 stops8h 20m
Southwest
Deal found 5/20![Southwest logo]()
$366
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/38:00 am
MDW
- MIA
Nonstop3h 00m
Southwest
Sat 7/118:45 pm
MIA
- MDW
1 stop11h 25m
Southwest
Deal found 5/20![Southwest logo]()
$376
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:23 am
MDW
- EYW
1 stop4h 49m
Delta
Wed 6/106:24 pm
EYW
- MDW
1 stop4h 53m
Delta
Deal found 5/22![Delta logo]()
$464
This Southwest deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:55 am
MDW
- MIA
Nonstop3h 00m
Southwest
Wed 6/1011:45 am
MIA
- MDW
1 stop5h 10m
Southwest
Deal found 5/24![Southwest logo]()
$381
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 7/2212:41 pm
MDW
- EYW
1 stop6h 10m
Delta
Sun 7/267:50 am
EYW
- MDW
1 stop5h 06m
Delta
Deal found 5/22![Delta logo]()
$494
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:45 am
MDW
- MIA
1 stop6h 00m
Southwest
Tue 6/212:10 pm
MIA
- MDW
2 stops9h 00m
Southwest
Deal found 5/20![Southwest logo]()
$400
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1811:05 am
MDW
- EYW
1 stop5h 22m
Delta
Thu 6/256:24 pm
EYW
- MDW
1 stop4h 53m
Delta
Deal found 5/21![Delta logo]()
$509
This Southwest deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 7/302:40 pm
MDW
- MIA
2 stops6h 25m
Southwest
Mon 8/35:25 am
MIA
- MDW
1 stop5h 35m
Southwest
Deal found 5/21![Southwest logo]()
$408
This Southwest deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 7/116:30 am
MDW
- MIA
2 stops8h 55m
Southwest
Mon 7/136:20 am
MIA
- MDW
2 stops8h 25m
Southwest
Deal found 5/21![Southwest logo]()
$409
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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
- EYW
1 stop5h 26m
Delta
Sat 8/1511:49 am
EYW
- MDW
1 stop4h 49m
Delta
Deal found 5/20![Delta logo]()
$549
This Southwest deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/102:40 pm
MDW
- MIA
2 stops6h 30m
Southwest
Mon 7/136:20 am
MIA
- MDW
1 stop5h 15m
Southwest
Deal found 5/22![Southwest logo]()
$418
This Delta deal was found by Cheapflights users on 5/23. 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.
Sat 7/256:00 am
MDW
- EYW
1 stop5h 09m
Delta
Wed 7/296:18 pm
EYW
- MDW
1 stop4h 57m
Delta
Deal found 5/23![Delta logo]()
$619
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/289:19 am
MDW
- EYW
2 stops7h 04m
Delta
Wed 8/511:49 am
EYW
- MDW
1 stop5h 26m
Delta
Deal found 5/21![Delta logo]()
$634
Last-minute flights from Midway to Florida KeysDiscover last-minute flight deals from Midway to Florida Keys. Data last updated May 25, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Florida Keys. Data last updated May 25, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:53 pm
MDW
- EYW
1 stop5h 56m
Delta
Wed 6/1711:59 am
EYW
- MDW
1 stop5h 17m
Delta
Deal found 5/24![Delta logo]()
$356
This Frontier deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1311:59 am
MDW
- MIA
1 stop10h 35m
Frontier
Tue 6/165:26 pm
MIA
- MDW
1 stop5h 45m
Frontier
Deal found 5/24![Frontier logo]()
$243
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 6/168:10 am
MDW
- MIA
1 stop5h 15m
Southwest
Wed 6/174:00 pm
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 5/20![Southwest logo]()
$225
This Frontier deal was found by Cheapflights users on 5/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/176:00 am
MDW
- MIA
1 stop9h 31m
Frontier
Wed 6/2411:19 am
MIA
- MDW
1 stop11h 52m
Frontier
Deal found 5/23![Frontier logo]()
$230
This Frontier deal was found by Cheapflights users on 5/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/186:00 am
MDW
- MIA
1 stop9h 31m
Frontier
Tue 6/2311:19 am
MIA
- MDW
1 stop11h 52m
Frontier
Deal found 5/23![Frontier logo]()
$249
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1912:50 pm
MDW
- EYW
1 stop6h 03m
Delta
Mon 6/226:24 pm
EYW
- MDW
1 stop4h 53m
Delta
Deal found 5/20![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/2311:05 am
MDW
- MIA
1 stop7h 16m
Delta
Wed 6/244:00 pm
MIA
- MDW
1 stop7h 17m
Delta
Deal found 5/20![Delta logo]()
$239
This Priceline deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/236:00 am
MDW
- MIA
1 stop6h 49m
Frontier
Thu 6/255:26 pm
MIA
- MDW
1 stop5h 45m
Frontier
Deal found 5/24![Frontier logo]()
$247
This Southwest deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2411:45 am
MDW
- MIA
Nonstop3h 00m
Southwest
Wed 7/14:00 pm
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 5/24![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/243:00 pm
MDW
- MIA
2 stops6h 10m
Southwest
Tue 6/3011:45 am
MIA
- MDW
1 stop5h 10m
Southwest
Deal found 5/21![Southwest logo]()
$240
This Trip.com deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/246:00 am
MDW
- MIA
1 stop6h 49m
Frontier
Tue 6/305:26 pm
MIA
- MDW
1 stop5h 45m
Frontier
Deal found 5/24![Frontier logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/282:46 pm
MDW
- EYW
1 stop17h 55m
Multiple Airlines
Thu 7/212:05 pm
EYW
- MDW
2 stops11h 06m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$350
One-way flights from Midway to Florida KeysSearch for one-way flight options from Midway to Florida Keys. Find affordable one-way fares based on user searches. Data last updated May 25, 2026.
Search for one-way flight options from Midway to Florida Keys. Find affordable one-way fares based on user searches. Data last updated May 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 6/2412:04 pm
MDW
- MIA
1 stop9h 59m
Frontier
Deal found 5/20![Frontier logo]()
$81
This Kissandfly.com deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
MDW
- MIA
1 stop6h 49m
Frontier
Deal found 5/25![Frontier logo]()
$93
This Southwest deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 8/189:25 am
MDW
- MIA
Nonstop3h 00m
Southwest
Deal found 5/22![Southwest logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/62:49 pm
MDW
- EYW
1 stop17h 52m
Allegiant Air
Deal found 5/22![Allegiant Air logo]()
$104
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2411:45 am
MDW
- MIA
Nonstop3h 00m
Southwest
Deal found 5/20![Southwest logo]()
$110
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2411:05 am
MDW
- MIA
1 stop7h 51m
Delta
Deal found 5/22![Delta logo]()
$111
This Super.com deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:00 am
MDW
- MIA
1 stop6h 49m
Frontier
Deal found 5/24![Frontier logo]()
$114
This Frontier deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:05 am
MDW
- MIA
1 stop6h 48m
Frontier
Deal found 5/24![Frontier logo]()
$116
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 7/184:22 pm
MDW
- MIA
1 stop7h 33m
Delta
Deal found 5/22![Delta logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 6/112:46 pm
MDW
- EYW
1 stop17h 55m
Allegiant Air
Deal found 5/22![Allegiant Air logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/812:11 pm
MDW
- EYW
2 stops22h 14m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/212:46 pm
MDW
- EYW
1 stop17h 55m
Allegiant Air
Deal found 5/21![Allegiant Air logo]()
$195
Find flight deals from Midway to Florida Keys
Keep the following information in mind while searching for Midway to Florida Keys flight deals. Data was last updated May 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $219 (Southwest) |
One-way from | $81 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $315 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Florida Keys that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 25, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Florida Keys that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 8/4
2:40 pm-8:10 pm
1 stop4h 30m
Miami
Wed 12/16
9:30 am-5:10 pm
2 stops8h 40m
$293
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Thu 8/13
12:46 pm-7:54 pm
1 stop6h 08m
Key West
Tue 8/18
7:40 am-11:51 am
1 stop5h 11m
$329
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Fri 8/14
10:54 am-5:20 pm
1 stop5h 26m
Key West
Tue 8/18
7:40 am-11:51 am
1 stop5h 11m
$329
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 7/7
11:45 am-3:45 pm
Nonstop3h 00m
Miami
Sat 7/11
8:45 pm-7:10 am
1 stop11h 25m
$333
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Fri 6/19
8:00 am-12:00 pm
Nonstop3h 00m
Miami
Tue 6/23
4:20 pm-9:10 pm
1 stop5h 50m
$364
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Thu 8/13
7:25 am-3:20 pm
1 stop6h 55m
Miami
Sun 8/16
6:45 am-2:05 pm
2 stops8h 20m
$366
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Fri 7/3
8:00 am-12:00 pm
Nonstop3h 00m
Miami
Sat 7/11
8:45 pm-7:10 am
1 stop11h 25m
$376
Quickest round-trip
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 6/3
7:55 am-11:55 am
Nonstop3h 00m
Miami
Wed 6/10
11:45 am-3:55 pm
1 stop5h 10m
$381
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 5/30
7:45 am-2:45 pm
1 stop6h 00m
Miami
Tue 6/2
12:10 pm-8:10 pm
2 stops9h 00m
$400
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Thu 7/30
2:40 pm-10:05 pm
2 stops6h 25m
Miami
Mon 8/3
5:25 am-10:00 am
1 stop5h 35m
$408
Showing 1-10 of 36 resultsSorted by cheapest first
Best time to book a flight from Midway to Florida Keys
Have a flexible travel schedule? Discover the best time to fly to Florida Keys from Midway with our price prediction graph.
MDW-MIA
MDW-EYW
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 Keys
MDW-zzEOA
MDW-MIA
MDW-EYW
What is the cheapest month to book a flight from Chicago Midway Airport to Florida Keys?
Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Florida Keys (average of $39). Flying from Chicago Midway Airport to Florida Keys in September is currently the most expensive (average of $185). 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.
How far ahead should I book a flight from Chicago Midway Airport to Florida Keys?
The best time to book flights from Chicago Midway Airport to Florida Keys is 22 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Reviews of airlines servicing Florida Keys
Get insights into the airlines that provide service to Florida Keys. 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 Keys. Reviews last updated May 25, 2026.
Read reviews from past customers who have flown Southwest,Delta, andAmerican Airlines from Chicago Midway Airport to Florida Keys. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Overall
7.9
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Overall
7.9
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Overall
7.9
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Overall
7.9
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Spirit Airlines
Crew
8.6
Overall
7.9
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Overall
7.9
Comfort
8.0
Food
7.0
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 Keys. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Alternative routes for Midway to Florida Keys
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Florida Keys by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Florida Keys by cabin class
Find flights from Midway to Florida Keys, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Florida Keys flights
Browse other Midway and Florida Keys flight options. Last updated on May 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Midway to Florida Keys
Discover the top airline that operate flights from Midway to Florida Keys. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$268 | Average$508 | FlexibilityNo cancel fee | On-timeN/A |