$47+ 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 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
Apr 3 — Apr 101
Round-trip
1 adult, Economy
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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
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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
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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 March 4, 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 March 4, 2026.
This Frontier deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/76:00 am
MDW
- MIA
Nonstop3h 13m
Frontier
Sat 3/1411:13 am
MIA
- MDW
Nonstop3h 28m
Frontier
Deal found 3/1![Frontier logo]()
$99
This Frontier deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/46:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Fri 4/1011:35 am
MIA
- MDW
Nonstop3h 26m
Frontier
Deal found 3/1![Frontier logo]()
$100
This Trip.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Sat 4/185:05 am
MIA
- MDW
1 stop14h 32m
Frontier
Deal found 2/28![Frontier logo]()
$101
This Trip.com deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Wed 4/151:10 pm
MIA
- MDW
1 stop7h 21m
Frontier
Deal found 2/27![Frontier logo]()
$102
This Super.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/156:00 am
MDW
- MIA
Nonstop3h 13m
Frontier
Thu 3/1911:13 am
MIA
- MDW
Nonstop3h 28m
Frontier
Deal found 2/28![Frontier logo]()
$103
This Frontier deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/96:00 am
MDW
- MIA
Nonstop3h 13m
Frontier
Sat 3/1411:13 am
MIA
- MDW
Nonstop3h 28m
Frontier
Deal found 2/28![Frontier logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/46:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Wed 4/85:05 am
MIA
- MDW
1 stop16h 02m
Frontier
Deal found 3/3![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 4/116:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Tue 4/147:04 pm
MIA
- MDW
1 stop25h 27m
Frontier
Deal found 3/4![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Tue 4/211:05 pm
MIA
- MDW
1 stop7h 26m
Frontier
Deal found 2/28![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/116:30 am
MDW
- MIA
Nonstop3h 10m
Multiple Airlines
Tue 4/143:12 pm
MIA
- MDW
1 stop8h 02m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:30 am
MDW
- MIA
Nonstop3h 10m
Multiple Airlines
Sat 4/184:59 pm
MIA
- MDW
1 stop6h 15m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$113
This WAYA deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/256:48 pm
MDW
- MIA
Nonstop3h 08m
Multiple Airlines
Tue 3/313:12 pm
MIA
- MDW
1 stop6h 42m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$114
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 March 4, 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 March 4, 2026.
This Southwest deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 5/93:45 pm
MDW
- MIA
Nonstop2h 55m
Southwest
Sat 5/167:00 am
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 3/4![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/16:07 pm
MDW
- MIA
1 stop5h 45m
Delta
Tue 4/146:00 am
MIA
- MDW
1 stop7h 07m
Delta
Deal found 3/1![Delta logo]()
$252
This Southwest deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 4/287:55 am
MDW
- MIA
Nonstop3h 00m
Southwest
Sun 5/36:45 am
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 3/2![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/412:10 pm
MDW
- MIA
1 stop6h 20m
Southwest
Thu 4/96:40 am
MIA
- MDW
2 stops7h 30m
Southwest
Deal found 2/27![Southwest logo]()
$269
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/316:07 pm
MDW
- MIA
1 stop5h 45m
Delta
Fri 4/36:00 am
MIA
- MDW
1 stop4h 56m
Delta
Deal found 2/28![Delta logo]()
$328
This Delta deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:00 am
MDW
- MIA
1 stop7h 12m
Delta
Sun 4/196:00 am
MIA
- MDW
1 stop4h 56m
Delta
Deal found 2/27![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/211:15 am
MDW
- MIA
1 stop5h 10m
Southwest
Tue 4/76:40 am
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 3/1![Southwest logo]()
$320
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/3012:47 pm
MDW
- EYW
1 stop5h 54m
Delta
Tue 4/76:25 pm
EYW
- MDW
1 stop5h 06m
Delta
Deal found 2/28![Delta logo]()
$345
This Southwest deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/259:00 am
MDW
- MIA
1 stop7h 30m
Southwest
Sat 5/306:35 am
MIA
- MDW
2 stops9h 05m
Southwest
Deal found 3/3![Southwest logo]()
$331
This Southwest deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/37:30 pm
MDW
- MIA
Nonstop3h 00m
Southwest
Wed 4/86:40 am
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 3/3![Southwest logo]()
$333
This Delta deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/1712:52 pm
MDW
- EYW
1 stop5h 48m
Delta
Tue 4/216:23 pm
EYW
- MDW
1 stop5h 05m
Delta
Deal found 3/3![Delta logo]()
$392
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:50 pm
MDW
- MIA
Nonstop3h 00m
Southwest
Mon 4/206:05 pm
MIA
- MDW
Nonstop3h 20m
Southwest
Deal found 2/27![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/137:30 pm
MDW
- MIA
Nonstop3h 00m
Southwest
Wed 3/186:30 am
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 3/1![Southwest logo]()
$338
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2212:52 pm
MDW
- EYW
1 stop5h 48m
Delta
Sat 4/256:18 pm
EYW
- MDW
1 stop5h 10m
Delta
Deal found 2/28![Delta logo]()
$423
This Southwest deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 4/172:10 pm
MDW
- MIA
2 stops7h 50m
Southwest
Fri 4/247:15 pm
MIA
- MDW
1 stop5h 15m
Southwest
Deal found 3/2![Southwest logo]()
$350
This Delta deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2412:52 pm
MDW
- EYW
1 stop5h 48m
Delta
Mon 4/276:23 pm
EYW
- MDW
1 stop5h 05m
Delta
Deal found 2/27![Delta logo]()
$425
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/1312:47 pm
MDW
- EYW
1 stop5h 54m
Delta
Tue 3/176:25 pm
EYW
- MDW
1 stop5h 06m
Delta
Deal found 2/28![Delta logo]()
$584
This Delta deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/2010:45 am
MDW
- EYW
1 stop5h 45m
Delta
Tue 3/247:30 am
EYW
- MDW
1 stop5h 32m
Delta
Deal found 3/1![Delta logo]()
$619
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/1410:45 am
MDW
- EYW
1 stop5h 45m
Delta
Wed 3/186:25 pm
EYW
- MDW
1 stop5h 06m
Delta
Deal found 2/28![Delta logo]()
$784
This Delta deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
Sun 3/1512:47 pm
MDW
- EYW
1 stop5h 54m
Delta
Thu 3/196:25 pm
EYW
- MDW
1 stop5h 06m
Delta
Deal found 3/1![Delta logo]()
$968
Last-minute flights from Midway to Florida KeysDiscover last-minute flight deals from Midway to Florida Keys. Data last updated March 4, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Florida Keys. Data last updated March 4, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/76:00 am
MDW
- MIA
Nonstop3h 13m
Frontier
Sat 3/1411:13 am
MIA
- MDW
Nonstop3h 28m
Frontier
Deal found 3/1![Frontier logo]()
$99
This Frontier deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/96:00 am
MDW
- MIA
Nonstop3h 13m
Frontier
Sat 3/1411:13 am
MIA
- MDW
Nonstop3h 28m
Frontier
Deal found 2/28![Frontier logo]()
$104
This Super.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/156:00 am
MDW
- MIA
Nonstop3h 13m
Frontier
Thu 3/1911:13 am
MIA
- MDW
Nonstop3h 28m
Frontier
Deal found 2/28![Frontier logo]()
$103
This WAYA deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/256:48 pm
MDW
- MIA
Nonstop3h 08m
Multiple Airlines
Tue 3/313:12 pm
MIA
- MDW
1 stop6h 42m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$114
This Frontier deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/46:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Fri 4/1011:35 am
MIA
- MDW
Nonstop3h 26m
Frontier
Deal found 3/1![Frontier logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/46:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Wed 4/85:05 am
MIA
- MDW
1 stop16h 02m
Frontier
Deal found 3/3![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 4/116:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Tue 4/147:04 pm
MIA
- MDW
1 stop25h 27m
Frontier
Deal found 3/4![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Tue 4/211:05 pm
MIA
- MDW
1 stop7h 26m
Frontier
Deal found 2/28![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/116:30 am
MDW
- MIA
Nonstop3h 10m
Multiple Airlines
Tue 4/143:12 pm
MIA
- MDW
1 stop8h 02m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:30 am
MDW
- MIA
Nonstop3h 10m
Multiple Airlines
Sat 4/184:59 pm
MIA
- MDW
1 stop6h 15m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$113
This Trip.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Sat 4/185:05 am
MIA
- MDW
1 stop14h 32m
Frontier
Deal found 2/28![Frontier logo]()
$101
This Trip.com deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Wed 4/151:10 pm
MIA
- MDW
1 stop7h 21m
Frontier
Deal found 2/27![Frontier logo]()
$102
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 March 4, 2026.
Search for one-way flight options from Midway to Florida Keys. Find affordable one-way fares based on user searches. Data last updated March 4, 2026.
This Trip.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
Mon 3/96:00 am
MDW
- MIA
Nonstop3h 13m
Frontier
Deal found 3/2![Frontier logo]()
$47
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/136:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Deal found 3/3![Frontier logo]()
$48
This Frontier deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/156:00 am
MDW
- MIA
Nonstop3h 13m
Frontier
Deal found 2/27![Frontier logo]()
$49
This Super.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
Sat 4/46:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Deal found 3/1![Frontier logo]()
$59
This Frontier deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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.
Mon 3/166:00 am
MDW
- MIA
Nonstop3h 13m
Frontier
Deal found 3/3![Frontier logo]()
$60
This Trip.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/62:20 pm
MDW
- MIA
1 stop9h 29m
Frontier
Deal found 3/3![Frontier logo]()
$61
This Kiwi.com deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 5/96:00 am
MDW
- MIA
1 stop10h 57m
Frontier
Deal found 3/4![Frontier logo]()
$65
This Kiwi.com deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 5/26:00 am
MDW
- MIA
1 stop7h 15m
Frontier
Deal found 3/4![Frontier logo]()
$66
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 3/176:00 am
MDW
- MIA
1 stop13h 07m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$67
This eDestinos deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/52:20 pm
MDW
- MIA
1 stop9h 29m
Frontier
Deal found 3/2![Frontier logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/312:47 pm
MDW
- EYW
1 stop17h 54m
Allegiant Air
Deal found 2/27![Allegiant Air logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/244:33 pm
MDW
- EYW
1 stop17h 38m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$122
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 March 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $100 (Frontier) |
One-way from | $47 (Trip.com) |
Popular in | December |
Cheapest in | September |
Average price | $303 |
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 March 4, 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
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 5/9
3:45 pm-7:40 pm
Nonstop2h 55m
Miami
Sat 5/16
7:00 am-9:15 am
Nonstop3h 15m
$227
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 4/1
6:07 pm-12:52 am
1 stop5h 45m
Miami
Tue 4/14
6:00 am-12:07 pm
1 stop7h 07m
$252
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 4/28
7:55 am-11:55 am
Nonstop3h 00m
Miami
Sun 5/3
6:45 am-8:55 am
Nonstop3h 10m
$267
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 4/4
12:10 pm-7:30 pm
1 stop6h 20m
Miami
Thu 4/9
6:40 am-1:10 pm
2 stops7h 30m
$269
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Thu 4/2
11:15 am-5:25 pm
1 stop5h 10m
Miami
Tue 4/7
6:40 am-8:50 am
Nonstop3h 10m
$320
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 3/31
6:07 pm-12:52 am
1 stop5h 45m
Miami
Fri 4/3
6:00 am-9:56 am
1 stop4h 56m
$328
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Thu 4/16
6:00 am-2:12 pm
1 stop7h 12m
Miami
Sun 4/19
6:00 am-9:56 am
1 stop4h 56m
$329
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Mon 5/25
9:00 am-5:30 pm
1 stop7h 30m
Miami
Sat 5/30
6:35 am-2:40 pm
2 stops9h 05m
$331
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Fri 4/3
7:30 pm-11:30 pm
Nonstop3h 00m
Miami
Wed 4/8
6:40 am-8:50 am
Nonstop3h 10m
$333
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Thu 4/16
6:50 pm-10:50 pm
Nonstop3h 00m
Miami
Mon 4/20
6:05 pm-8:25 pm
Nonstop3h 20m
$337
Showing 1-10 of 37 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Florida Keys (average of $279). Flying from Chicago Midway Airport to Florida Keys in August is currently the most expensive (average of $548). 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.
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 March 4, 2026.
Read reviews from past customers who have flown Southwest, Delta, and United 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.
Overall
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
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 Keys. 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 Keys
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Complete your trip
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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 March 4, 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 March 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$268 | Average$478 | FlexibilityNo cancel fee | On-timeN/A |