$105+ Cheap flights from Chicago (CHI) 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EYW
Jul 9 — Jul 161
Round-trip
1 adult, Economy
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Find cheap flights from Chicago 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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Cheapest flights from Chicago to Florida KeysExplore the most affordable flight options available from Chicago to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 9, 2026.
Explore the most affordable flight options available from Chicago to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 9, 2026.
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/42:50 pm
ORD
- MIA
Nonstop3h 12m
American Airlines
Tue 11/105:05 pm
MIA
- ORD
Nonstop3h 28m
American Airlines
Deal found 6/9![American Airlines logo]()
$207
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 8/189:25 am
MDW
- MIA
Nonstop3h 00m
Southwest
Tue 8/254:00 pm
MIA
- MDW
Nonstop3h 05m
Southwest
Deal found 6/8![Southwest logo]()
$209
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/45:00 am
ORD
- MIA
Nonstop3h 09m
American Airlines
Tue 8/113:09 pm
MIA
- ORD
Nonstop3h 42m
American Airlines
Deal found 6/8![American Airlines logo]()
$209
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/252:50 pm
ORD
- MIA
Nonstop3h 12m
American Airlines
Wed 12/28:35 pm
MIA
- ORD
Nonstop3h 22m
American Airlines
Deal found 6/8![American Airlines logo]()
$213
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:00 am
ORD
- MIA
1 stop7h 46m
United Airlines
Tue 9/294:01 pm
MIA
- ORD
Nonstop3h 31m
United Airlines
Deal found 6/8![United Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/215:46 pm
ORD
- MIA
1 stop29h 45m
Frontier
Tue 7/286:30 am
MIA
- ORD
1 stop19h 19m
Frontier
Deal found 6/6![Frontier logo]()
$221
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:05 am
MDW
- MIA
1 stop6h 48m
Frontier
Wed 7/225:28 pm
MIA
- MDW
1 stop5h 35m
Frontier
Deal found 6/8![Frontier logo]()
$227
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 11/48:15 am
ORD
- MIA
1 stop5h 14m
Delta
Tue 11/1011:45 am
MIA
- ORD
1 stop5h 52m
Delta
Deal found 6/8![Delta logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 8/226:00 am
MDW
- MIA
1 stop6h 29m
Frontier
Sat 8/298:10 am
MIA
- MDW
1 stop15h 01m
Frontier
Deal found 6/4![Frontier logo]()
$228
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/19:48 pm
ORD
- MIA
1 stop31h 06m
Frontier
Tue 7/76:30 am
MIA
- ORD
1 stop19h 19m
Frontier
Deal found 6/9![Frontier logo]()
$228
This Frontier 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 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 stop9h 31m
Frontier
Wed 7/1511:19 am
MIA
- MDW
1 stop11h 44m
Frontier
Deal found 6/8![Frontier logo]()
$229
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/11:29 pm
ORD
- MIA
1 stop8h 34m
Frontier
Wed 7/1511:19 am
MIA
- ORD
1 stop9h 34m
Frontier
Deal found 6/8![Frontier logo]()
$229
Best flights from Chicago to Florida KeysDiscover carefully curated flight deals from Chicago to Florida Keys that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 9, 2026.
Discover carefully curated flight deals from Chicago to Florida Keys that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 9, 2026.
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1410:33 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Wed 7/224:10 pm
MIA
- ORD
Nonstop3h 43m
United Airlines
Deal found 6/8![United Airlines logo]()
$239
This Southwest deal was found by Cheapflights users on 6/4. 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.
Thu 8/138:00 am
MDW
- MIA
Nonstop3h 10m
Southwest
Tue 8/184:00 pm
MIA
- MDW
Nonstop3h 05m
Southwest
Deal found 6/4![Southwest logo]()
$253
This Delta deal was found by Cheapflights users on 6/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:40 am
ORD
- EYW
1 stop5h 20m
Delta
Mon 8/246:15 pm
EYW
- ORD
1 stop6h 47m
Delta
Deal found 6/4![Delta logo]()
$329
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/205:00 am
ORD
- MIA
Nonstop3h 09m
American Airlines
Thu 7/238:54 pm
MIA
- ORD
Nonstop3h 36m
American Airlines
Deal found 6/7![American Airlines logo]()
$438
This United Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:30 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Tue 8/185:01 pm
MIA
- ORD
1 stop7h 25m
United Airlines
Deal found 6/5![United Airlines logo]()
$263
This United Airlines deal was found by Cheapflights users on 6/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/174:00 pm
ORD
- MIA
1 stop6h 43m
United Airlines
Sat 10/244:01 pm
MIA
- ORD
Nonstop3h 31m
United Airlines
Deal found 6/4![United Airlines logo]()
$289
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 6/2411:45 am
MDW
- MIA
Nonstop3h 00m
Southwest
Tue 7/1411:45 am
MIA
- MDW
1 stop5h 10m
Southwest
Deal found 6/8![Southwest logo]()
$318
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 8/196:05 am
MDW
- EYW
1 stop5h 55m
Delta
Wed 8/266:15 pm
EYW
- MDW
1 stop5h 21m
Delta
Deal found 6/6![Delta logo]()
$339
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/710:33 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Tue 7/141:10 pm
MIA
- ORD
1 stop8h 22m
United Airlines
Deal found 6/8![United Airlines logo]()
$293
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/2111:50 am
MDW
- MIA
2 stops8h 35m
Southwest
Tue 7/2811:45 am
MIA
- MDW
1 stop5h 10m
Southwest
Deal found 6/6![Southwest logo]()
$348
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/167:00 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Tue 7/215:32 pm
MIA
- ORD
Nonstop3h 41m
United Airlines
Deal found 6/8![United Airlines logo]()
$311
This Delta deal was found by Cheapflights users on 6/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:05 am
MDW
- EYW
1 stop7h 47m
Delta
Wed 8/1211:48 am
EYW
- MDW
1 stop5h 27m
Delta
Deal found 6/4![Delta logo]()
$384
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/13:00 pm
MDW
- MIA
2 stops6h 10m
Southwest
Tue 7/76:00 am
MIA
- MDW
2 stops7h 15m
Southwest
Deal found 6/6![Southwest logo]()
$386
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/257:00 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Sat 8/15:32 pm
MIA
- ORD
Nonstop3h 41m
United Airlines
Deal found 6/7![United Airlines logo]()
$327
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 9/2210:48 am
MDW
- EYW
1 stop5h 36m
Delta
Mon 9/286:19 pm
EYW
- MDW
1 stop5h 06m
Delta
Deal found 6/8![Delta logo]()
$429
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.
Sat 7/114:50 pm
MDW
- MIA
1 stop5h 15m
Southwest
Mon 7/132:50 pm
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 6/8![Southwest logo]()
$391
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/238:10 am
MDW
- MIA
1 stop5h 15m
Southwest
Sat 6/276:10 am
MIA
- MDW
2 stops6h 50m
Southwest
Deal found 6/7![Southwest logo]()
$397
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/245:00 am
ORD
- MIA
1 stop8h 38m
United Airlines
Tue 6/304:12 pm
MIA
- ORD
Nonstop3h 45m
United Airlines
Deal found 6/8![United Airlines logo]()
$392
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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
Wed 7/84:00 pm
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 6/6![Southwest logo]()
$408
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.
Thu 7/911:05 am
MDW
- MIA
1 stop4h 20m
Southwest
Mon 7/132:50 pm
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 6/8![Southwest logo]()
$419
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/135:25 am
MIA
- MDW
2 stops9h 00m
Southwest
Deal found 6/6![Southwest logo]()
$423
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.
Sun 7/56:00 am
MDW
- EYW
1 stop5h 23m
Delta
Fri 7/106:18 pm
EYW
- MDW
1 stop4h 57m
Delta
Deal found 6/8![Delta logo]()
$623
This United Airlines deal was found by Cheapflights users on 6/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2410:38 am
ORD
- MIA
Nonstop3h 21m
United Airlines
Sun 9/274:01 pm
MIA
- ORD
Nonstop3h 31m
United Airlines
Deal found 6/4![United Airlines logo]()
$500
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/911:55 am
MDW
- MIA
2 stops9h 15m
Southwest
Fri 7/105:25 am
MIA
- MDW
2 stops9h 00m
Southwest
Deal found 6/7![Southwest logo]()
$423
This Delta deal was found by Cheapflights users on 6/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1412:46 pm
MDW
- EYW
1 stop6h 08m
Delta
Tue 8/1811:48 am
EYW
- MDW
2 stops7h 45m
Delta
Deal found 6/4![Delta logo]()
$634
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/2210:40 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Fri 6/2612:30 pm
MIA
- ORD
Nonstop3h 43m
United Airlines
Deal found 6/8![United Airlines logo]()
$515
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/283:05 pm
MDW
- MIA
2 stops6h 30m
Southwest
Fri 7/37:15 am
MIA
- MDW
1 stop7h 30m
Southwest
Deal found 6/5![Southwest logo]()
$428
This Delta deal was found by Cheapflights users on 6/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:28 am
ORD
- EYW
1 stop6h 32m
Delta
Sat 8/157:40 am
EYW
- ORD
2 stops9h 37m
Delta
Deal found 6/4![Delta logo]()
$634
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 10/11:00 pm
MDW
- EYW
1 stop5h 50m
Delta
Sun 10/46:19 pm
EYW
- MDW
1 stop5h 06m
Delta
Deal found 6/5![Delta logo]()
$639
This United Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/217:00 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Tue 6/235:39 pm
MIA
- ORD
Nonstop3h 43m
United Airlines
Deal found 6/5![United Airlines logo]()
$530
Last-minute flights from Chicago to Florida KeysDiscover last-minute flight deals from Chicago to Florida Keys. Data last updated June 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Florida Keys. Data last updated June 9, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 6/4. 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 Super.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
Tue 6/305:26 pm
MIA
- MDW
1 stop5h 45m
Frontier
Deal found 6/4![Frontier logo]()
$237
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:55 am
ORD
- MIA
1 stop5h 54m
Frontier
Sat 7/47:00 am
MIA
- ORD
1 stop9h 53m
Frontier
Deal found 6/8![Frontier logo]()
$236
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/19:48 pm
ORD
- MIA
1 stop31h 06m
Frontier
Tue 7/76:30 am
MIA
- ORD
1 stop19h 19m
Frontier
Deal found 6/9![Frontier logo]()
$228
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/11:29 pm
ORD
- MIA
1 stop8h 34m
Frontier
Wed 7/1511:19 am
MIA
- ORD
1 stop9h 34m
Frontier
Deal found 6/8![Frontier logo]()
$229
This Frontier 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 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 stop9h 31m
Frontier
Wed 7/1511:19 am
MIA
- MDW
1 stop11h 44m
Frontier
Deal found 6/8![Frontier logo]()
$229
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:55 am
ORD
- MIA
1 stop8h 36m
Frontier
Wed 7/811:19 am
MIA
- ORD
1 stop9h 34m
Frontier
Deal found 6/7![Frontier logo]()
$230
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:00 am
MDW
- MIA
1 stop9h 31m
Frontier
Tue 7/711:19 am
MIA
- MDW
1 stop11h 44m
Frontier
Deal found 6/8![Frontier logo]()
$230
This Super.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/46:00 am
MDW
- MIA
1 stop8h 14m
Frontier
Wed 7/85:28 pm
MIA
- MDW
1 stop5h 35m
Frontier
Deal found 6/6![Frontier logo]()
$236
This Super.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/1112:11 pm
MDW
- MIA
1 stop7h 18m
Frontier
Tue 7/145:28 pm
MIA
- MDW
1 stop5h 35m
Frontier
Deal found 6/6![Frontier logo]()
$235
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:05 am
MDW
- MIA
1 stop6h 48m
Frontier
Wed 7/225:28 pm
MIA
- MDW
1 stop5h 35m
Frontier
Deal found 6/8![Frontier logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/215:46 pm
ORD
- MIA
1 stop29h 45m
Frontier
Tue 7/286:30 am
MIA
- ORD
1 stop19h 19m
Frontier
Deal found 6/6![Frontier logo]()
$221
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2212:11 pm
MDW
- MIA
1 stop9h 54m
Frontier
Wed 7/295:28 pm
MIA
- MDW
1 stop5h 35m
Frontier
Deal found 6/7![Frontier logo]()
$228
One-way flights from Chicago to Florida KeysSearch for one-way flight options from Chicago to Florida Keys. Find affordable one-way fares based on user searches. Data last updated June 9, 2026.
Search for one-way flight options from Chicago to Florida Keys. Find affordable one-way fares based on user searches. Data last updated June 9, 2026.
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:05 pm
ORD
- MIA
Nonstop3h 22m
United Airlines
Deal found 6/8![United Airlines logo]()
$105
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 9/99:25 am
MDW
- MIA
Nonstop3h 00m
Southwest
Deal found 6/9![Southwest logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/255:46 pm
ORD
- MIA
1 stop29h 45m
Frontier
Deal found 6/6![Frontier logo]()
$108
This Trip.com deal was found by Cheapflights users on 6/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:55 am
ORD
- MIA
1 stop15h 08m
Frontier
Deal found 6/4![Frontier logo]()
$111
This Trip.com deal was found by Cheapflights users on 6/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:00 am
MDW
- MIA
1 stop6h 29m
Frontier
Deal found 6/4![Frontier logo]()
$111
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:55 am
ORD
- MIA
1 stop5h 54m
Frontier
Deal found 6/9![Frontier logo]()
$112
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/81:50 pm
ORD
- MIA
1 stop8h 15m
Frontier
Deal found 6/9![Frontier logo]()
$113
This iWofly deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:05 am
MDW
- MIA
1 stop6h 48m
Frontier
Deal found 6/6![Frontier logo]()
$113
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 8/46:40 am
ORD
- MIA
1 stop5h 20m
Delta
Deal found 6/8![Delta logo]()
$114
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:00 am
MDW
- MIA
1 stop6h 49m
Frontier
Deal found 6/9![Frontier logo]()
$114
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/139:20 am
ORD
- MIA
1 stop8h 02m
Frontier
Deal found 6/7![Frontier logo]()
$115
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:05 am
MDW
- MIA
1 stop6h 48m
Frontier
Deal found 6/8![Frontier logo]()
$115
Find flight deals from Chicago to Florida Keys
Keep the following information in mind while searching for Chicago to Florida Keys flight deals. Data was last updated June 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $207 (American Airlines) |
One-way from | $105 (Southwest) |
Popular in | June |
Cheapest in | September |
Average price | $359 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago 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 June 9, 2026.
Use the filters below to find and compare flights from Chicago to Florida Keys that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Tue 7/14
10:33 am-2:57 pm
Nonstop3h 24m
Miami
Wed 7/22
4:10 pm-6:53 pm
Nonstop3h 43m
$239
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Thu 8/13
8:00 am-12:10 pm
Nonstop3h 10m
Miami
Tue 8/18
4:00 pm-6:05 pm
Nonstop3h 05m
$253
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Thu 8/13
7:30 am-11:54 am
Nonstop3h 24m
Miami
Tue 8/18
5:01 pm-11:26 pm
1 stop7h 25m
$263
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Sat 10/17
4:00 pm-11:43 pm
1 stop6h 43m
Miami
Sat 10/24
4:01 pm-6:32 pm
Nonstop3h 31m
$289
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Tue 7/7
10:33 am-2:57 pm
Nonstop3h 24m
Miami
Tue 7/14
1:10 pm-8:32 pm
1 stop8h 22m
$293
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Thu 7/16
7:00 am-11:24 am
Nonstop3h 24m
Miami
Tue 7/21
5:32 pm-8:13 pm
Nonstop3h 41m
$311
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 6/24
11:45 am-3:45 pm
Nonstop3h 00m
Miami
Tue 7/14
11:45 am-3:55 pm
1 stop5h 10m
$318
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Sat 7/25
7:00 am-11:24 am
Nonstop3h 24m
Miami
Sat 8/1
5:32 pm-8:13 pm
Nonstop3h 41m
$327
ChicagoKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Mon 8/17
6:40 am-1:00 pm
1 stop5h 20m
Key West
Mon 8/24
6:15 pm-12:02 am
1 stop6h 47m
$329
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Wed 8/19
6:05 am-1:00 pm
1 stop5h 55m
Key West
Wed 8/26
6:15 pm-10:36 pm
1 stop5h 21m
$339
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Florida Keys
Have a flexible travel schedule? Discover the best time to fly to Florida Keys from Chicago with our price prediction graph.
ORD-MIA
MDW-MIA
ORD-EYW
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 to Florida Keys
CHI-zzEOA
ORD-MIA
MDW-MIA
ORD-EYW
MDW-EYW
What is the cheapest month to book a flight from Chicago to Florida Keys?
Currently, October is the cheapest month in which you can book a flight from Chicago to Florida Keys (average of $221). Flying from Chicago to Florida Keys in December is currently the most expensive (average of $404). 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 CHI to EOA?
Find hourly flight availability from Chicago to Florida Keys. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 9, 2026.
When flying from Chicago to Florida Keys, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Chicago to Florida Keys
Explore weekly flight availability from Chicago to Florida Keys. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 9, 2026.
The most flights from CHI to zzEOA are scheduled on a Monday (3 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).
How far ahead should I book a flight from Chicago to Florida Keys?
The price you pay for your flight from Chicago to Florida Keys may vary depending on when you book. For the best chance of a lower fare, look to book 32 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
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 June 9, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines from Chicago to Florida Keys. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Food
7.0
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 Chicago 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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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Chicago 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 Chicago to Florida Keys by cabin class
Find flights from Chicago to Florida Keys, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Florida Keys flights
Browse other Chicago and Florida Keys flight options. Last updated on June 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Chicago to Florida Keys
Discover the top 3 airlines that operate flights from Chicago 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 June 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$206 | Average$438 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$249 | Average$414 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$308 | Average$476 | FlexibilityNo cancel fee | On-time71% |