$48+ 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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EYW
May 9 — May 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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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 Chicago to Florida Keys
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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 April 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 April 9, 2026.
This CheapOair deal was found by Cheapflights users on 4/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/253:52 pm
ORD
- MIA
Nonstop3h 19m
Multiple Airlines
Sat 5/26:30 am
MIA
- ORD
1 stop11h 41m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$101
This CheapOair deal was found by Cheapflights users on 4/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/119:20 am
ORD
- MIA
Nonstop3h 08m
Spirit Airlines
Fri 5/159:30 pm
MIA
- ORD
Nonstop3h 26m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:40 am
ORD
- MIA
Nonstop3h 19m
Multiple Airlines
Wed 4/296:30 am
MIA
- ORD
1 stop11h 41m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$103
This WAYA deal was found by Cheapflights users on 4/6. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/24:28 pm
ORD
- MIA
1 stop7h 21m
Frontier
Thu 5/72:13 pm
MIA
- ORD
Nonstop3h 37m
Frontier
Deal found 4/6![Frontier logo]()
$104
This Trip.com deal was found by Cheapflights users on 4/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/184:28 pm
ORD
- MIA
1 stop7h 21m
Frontier
Sat 4/259:21 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 4/5![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/253:52 pm
ORD
- MIA
Nonstop3h 19m
Multiple Airlines
Fri 5/15:05 am
MIA
- ORD
1 stop6h 18m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$106
This Cheapflightsfares deal was found by Cheapflights users on 4/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/33:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Thu 5/76:00 am
MIA
- ORD
1 stop18h 01m
Frontier
Deal found 4/6![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/253:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Tue 5/511:23 am
MIA
- ORD
1 stop9h 28m
Frontier
Deal found 4/7![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/23:52 pm
ORD
- MIA
Nonstop3h 19m
Multiple Airlines
Tue 5/52:25 pm
MIA
- ORD
1 stop9h 36m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$109
This Frontier deal was found by Cheapflights users on 4/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/253:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Sat 5/25:05 am
MIA
- ORD
1 stop7h 28m
Frontier
Deal found 4/6![Frontier logo]()
$110
This WAYA deal was found by Cheapflights users on 4/6. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/184:28 pm
ORD
- MIA
1 stop7h 21m
Frontier
Thu 4/239:21 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 4/6![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/23:52 pm
ORD
- MIA
Nonstop3h 19m
Multiple Airlines
Sat 5/92:25 pm
MIA
- ORD
1 stop9h 36m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$112
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 April 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 April 9, 2026.
This Southwest deal was found by Cheapflights users on 4/6. 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.
Sat 5/29:10 am
MDW
- MIA
1 stop6h 50m
Southwest
Sat 5/97:00 am
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 4/6![Southwest logo]()
$167
This United Airlines deal was found by Cheapflights users on 4/8. 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.
Fri 5/86:13 pm
ORD
- MIA
Nonstop3h 20m
United Airlines
Tue 5/124:52 pm
MIA
- ORD
1 stop7h 23m
United Airlines
Deal found 4/8![United Airlines logo]()
$197
This Delta deal was found by Cheapflights users on 4/5. 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.
Fri 5/112:52 pm
MDW
- EYW
1 stop5h 48m
Delta
Tue 5/56:23 pm
EYW
- MDW
1 stop5h 05m
Delta
Deal found 4/5![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 4/9. 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 5/610:05 am
MDW
- MIA
1 stop6h 25m
Southwest
Sat 5/97:00 am
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 4/9![Southwest logo]()
$167
This Southwest deal was found by Cheapflights users on 4/5. 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.
Sat 6/63:30 pm
MDW
- MIA
1 stop5h 55m
Southwest
Wed 6/1011:45 am
MIA
- MDW
1 stop5h 10m
Southwest
Deal found 4/5![Southwest logo]()
$172
This United Airlines deal was found by Cheapflights users on 4/5. 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.
Fri 5/296:05 pm
ORD
- MIA
Nonstop3h 22m
United Airlines
Tue 6/28:48 am
MIA
- ORD
1 stop7h 00m
United Airlines
Deal found 4/5![United Airlines logo]()
$198
This Southwest deal was found by Cheapflights users on 4/4. 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 5/99:05 am
MDW
- MIA
1 stop7h 10m
Southwest
Mon 5/116:05 am
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 4/4![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 4/5. 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.
Tue 5/52:35 pm
MDW
- MIA
2 stops6h 20m
Southwest
Tue 5/1212:35 pm
MIA
- MDW
1 stop7h 55m
Southwest
Deal found 4/5![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 4/5. 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.
Thu 5/283:05 pm
ORD
- MIA
1 stop5h 55m
Southwest
Tue 6/25:45 pm
MIA
- ORD
1 stop5h 10m
Southwest
Deal found 4/5![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/511:55 am
ORD
- MIA
2 stops9h 00m
Southwest
Tue 5/1212:35 pm
MIA
- ORD
2 stops10h 20m
Southwest
Deal found 4/9![Southwest logo]()
$187
This United Airlines deal was found by Cheapflights users on 4/7. 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.
Fri 5/16:13 pm
ORD
- MIA
Nonstop3h 20m
United Airlines
Fri 5/87:40 pm
MIA
- ORD
Nonstop3h 40m
United Airlines
Deal found 4/7![United Airlines logo]()
$287
This Delta deal was found by Cheapflights users on 4/4. 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 5/1211:26 am
ORD
- EYW
1 stop4h 57m
Delta
Tue 5/196:19 pm
EYW
- ORD
1 stop5h 08m
Delta
Deal found 4/4![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 4/4. 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.
Fri 5/156:50 pm
MDW
- MIA
Nonstop3h 00m
Southwest
Mon 5/181:45 pm
MIA
- MDW
1 stop7h 30m
Southwest
Deal found 4/4![Southwest logo]()
$187
This United Airlines deal was found by Cheapflights users on 4/4. 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.
Wed 6/177:00 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Wed 6/2412:30 pm
MIA
- ORD
Nonstop3h 43m
United Airlines
Deal found 4/4![United Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 4/8. 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 6/306:05 am
MDW
- EYW
1 stop6h 33m
Delta
Wed 7/86:18 pm
EYW
- MDW
1 stop4h 57m
Delta
Deal found 4/8![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 4/7. 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 8/1510:55 am
ORD
- EYW
Nonstop3h 11m
United Airlines
Sat 8/224:05 pm
EYW
- ORD
Nonstop3h 25m
United Airlines
Deal found 4/7![United Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 4/5. 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 5/107:40 am
MDW
- MIA
Nonstop3h 00m
Southwest
Thu 5/1411:40 am
MIA
- MDW
1 stop6h 20m
Southwest
Deal found 4/5![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/95:15 am
ORD
- EYW
1 stop4h 45m
Delta
Sat 8/153:10 pm
EYW
- ORD
1 stop6h 07m
Delta
Deal found 4/7![Delta logo]()
$374
This United Airlines deal was found by Cheapflights users on 4/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/65:00 am
ORD
- EYW
1 stop7h 45m
United Airlines
Wed 5/132:49 pm
EYW
- ORD
1 stop7h 51m
United Airlines
Deal found 4/6![United Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 4/4. 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 5/211:18 am
MDW
- EYW
1 stop5h 05m
Delta
Tue 5/127:30 am
EYW
- MDW
1 stop5h 26m
Delta
Deal found 4/4![Delta logo]()
$384
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/253:45 pm
MDW
- MIA
Nonstop2h 55m
Southwest
Thu 4/306:05 pm
MIA
- MDW
Nonstop3h 20m
Southwest
Deal found 4/7![Southwest logo]()
$247
This United Airlines deal was found by Cheapflights users on 4/4. 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 4/186:25 pm
ORD
- MIA
Nonstop3h 20m
United Airlines
Tue 4/214:18 pm
MIA
- ORD
Nonstop3h 39m
United Airlines
Deal found 4/4![United Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 4/4. 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.
Wed 6/312:53 pm
MDW
- EYW
1 stop5h 56m
Delta
Tue 6/96:24 pm
EYW
- MDW
1 stop4h 53m
Delta
Deal found 4/4![Delta logo]()
$397
This Southwest deal was found by Cheapflights users on 4/9. 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.
Sun 5/246:00 pm
MDW
- MIA
Nonstop2h 55m
Southwest
Fri 5/291:45 pm
MIA
- MDW
1 stop7h 30m
Southwest
Deal found 4/9![Southwest logo]()
$257
This United Airlines deal was found by Cheapflights users on 4/7. 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.
Fri 5/86:13 pm
ORD
- MIA
Nonstop3h 20m
United Airlines
Mon 5/117:40 pm
MIA
- ORD
Nonstop3h 40m
United Airlines
Deal found 4/7![United Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 4/6. 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.
Tue 6/306:40 am
ORD
- EYW
1 stop5h 58m
Delta
Mon 7/611:48 am
EYW
- ORD
1 stop7h 54m
Delta
Deal found 4/6![Delta logo]()
$404
This Southwest deal was found by Cheapflights users on 4/8. 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 4/2512:45 pm
MDW
- MIA
2 stops8h 20m
Southwest
Sat 5/26:15 am
MIA
- MDW
1 stop5h 30m
Southwest
Deal found 4/8![Southwest logo]()
$262
This United Airlines deal was found by Cheapflights users on 4/4. 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 7/46:05 pm
ORD
- MIA
Nonstop3h 22m
United Airlines
Mon 7/65:40 pm
MIA
- ORD
Nonstop3h 44m
United Airlines
Deal found 4/4![United Airlines logo]()
$350
This United Airlines deal was found by Cheapflights users on 4/5. 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.
Tue 4/216:25 pm
ORD
- MIA
Nonstop3h 20m
United Airlines
Fri 4/244:18 pm
MIA
- ORD
Nonstop3h 39m
United Airlines
Deal found 4/5![United Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 4/5. 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.
Sat 4/251:55 pm
ORD
- MIA
2 stops7h 10m
Southwest
Fri 5/16:20 am
MIA
- ORD
2 stops10h 10m
Southwest
Deal found 4/5![Southwest logo]()
$277
Last-minute flights from Chicago to Florida KeysDiscover last-minute flight deals from Chicago to Florida Keys. Data last updated April 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Florida Keys. Data last updated April 9, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:40 am
ORD
- MIA
Nonstop3h 19m
Multiple Airlines
Wed 4/296:30 am
MIA
- ORD
1 stop11h 41m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$103
This Trip.com deal was found by Cheapflights users on 4/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/184:28 pm
ORD
- MIA
1 stop7h 21m
Frontier
Sat 4/259:21 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 4/5![Frontier logo]()
$105
This WAYA deal was found by Cheapflights users on 4/6. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/184:28 pm
ORD
- MIA
1 stop7h 21m
Frontier
Thu 4/239:21 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 4/6![Frontier logo]()
$111
This CheapOair deal was found by Cheapflights users on 4/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/253:52 pm
ORD
- MIA
Nonstop3h 19m
Multiple Airlines
Sat 5/26:30 am
MIA
- ORD
1 stop11h 41m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/253:52 pm
ORD
- MIA
Nonstop3h 19m
Multiple Airlines
Fri 5/15:05 am
MIA
- ORD
1 stop6h 18m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/253:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Tue 5/511:23 am
MIA
- ORD
1 stop9h 28m
Frontier
Deal found 4/7![Frontier logo]()
$108
This Frontier deal was found by Cheapflights users on 4/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/253:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Sat 5/25:05 am
MIA
- ORD
1 stop7h 28m
Frontier
Deal found 4/6![Frontier logo]()
$110
This WAYA deal was found by Cheapflights users on 4/6. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/24:28 pm
ORD
- MIA
1 stop7h 21m
Frontier
Thu 5/72:13 pm
MIA
- ORD
Nonstop3h 37m
Frontier
Deal found 4/6![Frontier logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/23:52 pm
ORD
- MIA
Nonstop3h 19m
Multiple Airlines
Tue 5/52:25 pm
MIA
- ORD
1 stop9h 36m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/23:52 pm
ORD
- MIA
Nonstop3h 19m
Multiple Airlines
Sat 5/92:25 pm
MIA
- ORD
1 stop9h 36m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$112
This Cheapflightsfares deal was found by Cheapflights users on 4/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/33:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Thu 5/76:00 am
MIA
- ORD
1 stop18h 01m
Frontier
Deal found 4/6![Frontier logo]()
$107
This CheapOair deal was found by Cheapflights users on 4/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/119:20 am
ORD
- MIA
Nonstop3h 08m
Spirit Airlines
Fri 5/159:30 pm
MIA
- ORD
Nonstop3h 26m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$102
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 April 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 April 9, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 4/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/144:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$48
This Super.com deal was found by Cheapflights users on 4/8. 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.
Mon 4/1311:59 am
ORD
- MIA
Nonstop3h 19m
Frontier
Deal found 4/8![Frontier logo]()
$49
This Super.com deal was found by Cheapflights users on 4/8. 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.
Mon 4/136:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Deal found 4/8![Frontier logo]()
$49
This Spirit deal was found by Cheapflights users on 4/7. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/79:20 am
ORD
- MIA
Nonstop3h 08m
Spirit Airlines
Deal found 4/7![Spirit Airlines logo]()
$50
This Super.com deal was found by Cheapflights users on 4/6. 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.
Thu 4/233:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Deal found 4/6![Frontier logo]()
$52
This CheapOair deal was found by Cheapflights users on 4/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/134:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Deal found 4/8![Spirit Airlines logo]()
$54
This CheapOair deal was found by Cheapflights users on 4/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:50 am
ORD
- MIA
Nonstop3h 08m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$55
This Booking.com deal was found by Cheapflights users on 4/5. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/119:20 am
ORD
- MIA
Nonstop3h 08m
Spirit Airlines
Deal found 4/5![Spirit Airlines logo]()
$56
This Cheapflightsfares deal was found by Cheapflights users on 4/9. 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.
Sun 4/1210:55 am
ORD
- MIA
Nonstop3h 05m
Spirit Airlines
Deal found 4/9![Spirit Airlines logo]()
$60
This Cheapflightsfares deal was found by Cheapflights users on 4/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3011:28 am
ORD
- MIA
1 stop10h 03m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$61
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/93:07 pm
MDW
- MIA
1 stop21h 21m
Frontier
Deal found 4/8![Frontier logo]()
$65
This Trip.com deal was found by Cheapflights users on 4/4. 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.
Sat 4/186:00 am
MDW
- MIA
1 stop7h 10m
Frontier
Deal found 4/4![Frontier logo]()
$66
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 April 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $101 (CheapOair) |
One-way from | $48 (Cheapflightsfares) |
Popular in | December |
Cheapest in | September |
Average price | $261 |
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 April 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
MDW - MIA
MDWMIA
Chicago Midway
Sat 5/2
9:10 am-5:00 pm
1 stop6h 50m
Miami
Sat 5/9
7:00 am-9:15 am
Nonstop3h 15m
$167
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 5/6
10:05 am-5:30 pm
1 stop6h 25m
Miami
Sat 5/9
7:00 am-9:15 am
Nonstop3h 15m
$167
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 6/6
3:30 pm-10:25 pm
1 stop5h 55m
Miami
Wed 6/10
11:45 am-3:55 pm
1 stop5h 10m
$172
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 5/9
9:05 am-5:15 pm
1 stop7h 10m
Miami
Mon 5/11
6:05 am-8:20 am
Nonstop3h 15m
$177
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 5/5
2:35 pm-9:55 pm
2 stops6h 20m
Miami
Tue 5/12
12:35 pm-7:30 pm
1 stop7h 55m
$182
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Thu 5/28
3:05 pm-10:00 pm
1 stop5h 55m
Miami
Tue 6/2
5:45 pm-9:55 pm
1 stop5h 10m
$187
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Tue 5/5
11:55 am-9:55 pm
2 stops9h 00m
Miami
Tue 5/12
12:35 pm-9:55 pm
2 stops10h 20m
$187
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Fri 5/15
6:50 pm-10:50 pm
Nonstop3h 00m
Miami
Mon 5/18
1:45 pm-8:15 pm
1 stop7h 30m
$187
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Fri 5/8
6:13 pm-10:33 pm
Nonstop3h 20m
Miami
Tue 5/12
4:52 pm-11:15 pm
1 stop7h 23m
$197
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Fri 5/29
6:05 pm-10:27 pm
Nonstop3h 22m
Miami
Tue 6/2
8:48 am-2:48 pm
1 stop7h 00m
$198
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
MDW-EYW
ORD-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
MDW-EYW
ORD-EYW
What is the cheapest month to book a flight from Chicago to Florida Keys?
Currently, January is the cheapest month in which you can book a flight from Chicago to Florida Keys (average of $245). Flying from Chicago to Florida Keys in November is currently the most expensive (average of $323). 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 April 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 April 9, 2026.
The most flights from CHI to zzEOA are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).
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 April 9, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican 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.
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
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.
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.
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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 April 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Chicago to Florida Keys
Discover the top 4 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 April 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$145 | Average$376 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$248 | Average$431 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$249 | Average$421 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$309 | Average$467 | FlexibilityNo cancel fee | On-time71% |