$87+ 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EYW
Sep 22 — Sep 291
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 August 23, 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 August 23, 2026.
This American Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/14:35 pm -
Nonstop3h 20m
Sat 10/37:13 pm -
Nonstop3h 27m
Deal found 8/21![American Airlines logo]()
$172
This American Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/122:30 pm -
Nonstop3h 17m
Mon 9/145:15 am -
Nonstop3h 33m
Deal found 8/20![American Airlines logo]()
$173
This Trip.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:25 am -
1 stop9h 04m
Fri 9/185:34 pm -
1 stop7h 10m
Deal found 8/23![Frontier logo]()
$173
This American Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/122:30 pm -
Nonstop3h 17m
Sat 9/198:22 am -
Nonstop3h 28m
Deal found 8/22![American Airlines logo]()
$174
This Cheapflightsfares deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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.
Fri 9/251:01 pm -
1 stop7h 59m
Sat 9/267:23 am -
1 stop12h 04m
Deal found 8/18![Frontier logo]()
$175
This American Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:59 pm -
Nonstop3h 09m
Sat 10/248:37 am -
Nonstop3h 33m
Deal found 8/22![American Airlines logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/121:06 pm -
1 stop7h 54m
Thu 9/174:30 pm -
1 stop8h 14m
Deal found 8/22![Frontier logo]()
$176
This United Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 10/217:30 am -
Nonstop3h 25m
Tue 10/278:45 am -
1 stop7h 06m
Deal found 8/19![United Airlines logo]()
$177
This Expedia deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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.
Fri 9/1112:54 pm -
1 stop8h 06m
Mon 9/145:34 pm -
1 stop7h 10m
Deal found 8/19![Frontier logo]()
$177
This Trip.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/171:01 pm -
1 stop7h 59m
Mon 9/215:50 am -
1 stop19h 33m
Deal found 8/19![Frontier logo]()
$178
This Trip.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/146:25 am -
1 stop9h 04m
Thu 9/174:30 pm -
1 stop8h 14m
Deal found 8/18![Frontier logo]()
$178
This Cheapflightsfares deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 10/156:00 am -
1 stop10h 35m
Mon 10/1911:15 am -
1 stop28h 10m
Deal found 8/19![Frontier logo]()
$180
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 August 23, 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 August 23, 2026.
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 11/117:00 am -
Nonstop3h 11m
Mon 11/237:00 am -
1 stop8h 12m
Deal found 8/18![United Airlines logo]()
$191
This Southwest deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/39:55 am -
1 stop9h 35m
Mon 10/56:40 am -
Nonstop3h 05m
Deal found 8/22![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/169:53 am -
1 stop5h 02m
Thu 11/2611:34 am -
1 stop6h 29m
Deal found 8/21![Delta logo]()
$217
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/124:19 pm -
1 stop7h 38m
Wed 12/161:10 pm -
1 stop5h 54m
Deal found 8/18![Delta logo]()
$248
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/151:25 pm -
Nonstop3h 00m
Wed 12/236:25 pm -
Nonstop3h 20m
Deal found 8/19![Southwest logo]()
$253
This United Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 10/177:25 am -
Nonstop3h 25m
Wed 10/2112:29 pm -
Nonstop3h 31m
Deal found 8/19![United Airlines logo]()
$271
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:27 pm -
1 stop6h 49m
Tue 10/206:20 pm -
1 stop5h 13m
Deal found 8/20![Delta logo]()
$258
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2312:50 pm -
2 stops6h 15m
Mon 9/287:15 am -
Nonstop3h 05m
Deal found 8/20![Southwest logo]()
$268
This United Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:30 am -
Nonstop3h 25m
Sat 10/37:00 am -
1 stop6h 54m
Deal found 8/21![United Airlines logo]()
$281
This Southwest deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1211:20 am -
Nonstop3h 00m
Sat 9/196:30 am -
1 stop5h 10m
Deal found 8/22![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/511:45 am -
2 stops7h 35m
Sat 9/126:30 am -
2 stops7h 35m
Deal found 8/18![Southwest logo]()
$299
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/161:00 pm -
1 stop6h 00m
Tue 9/226:19 pm -
1 stop5h 25m
Deal found 8/19![Delta logo]()
$331
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/161:00 pm -
1 stop6h 00m
Wed 9/236:19 pm -
1 stop5h 25m
Deal found 8/20![Delta logo]()
$331
This United Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/89:00 am -
Nonstop3h 21m
Sun 10/114:01 pm -
Nonstop3h 31m
Deal found 8/21![United Airlines logo]()
$374
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 11/191:20 pm -
2 stops7h 50m
Thu 12/35:30 pm -
1 stop5h 00m
Deal found 8/18![Southwest logo]()
$317
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/245:30 am -
1 stop6h 38m
Tue 2/26:00 pm -
1 stop6h 50m
Deal found 8/20![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/183:10 pm -
2 stops6h 00m
Tue 9/2211:50 am -
1 stop7h 55m
Deal found 8/19![Southwest logo]()
$337
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:00 am -
1 stop7h 46m
Sat 9/512:17 pm -
Nonstop3h 31m
Deal found 8/22![United Airlines logo]()
$436
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2411:33 am -
1 stop7h 28m
Thu 10/296:10 pm -
1 stop5h 23m
Deal found 8/21![Delta logo]()
$366
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 10/292:30 pm -
2 stops7h 35m
Sun 11/15:05 am -
2 stops7h 55m
Deal found 8/19![Southwest logo]()
$354
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:30 am -
1 stop8h 25m
Wed 9/912:17 pm -
Nonstop3h 31m
Deal found 8/22![United Airlines logo]()
$467
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/11:00 pm -
1 stop6h 02m
Sat 12/56:02 pm -
1 stop5h 54m
Deal found 8/21![Delta logo]()
$393
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/224:15 pm -
2 stops5h 50m
Mon 10/266:40 pm -
2 stops12h 05m
Deal found 8/21![Southwest logo]()
$366
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/2610:35 am -
1 stop5h 36m
Thu 2/46:00 pm -
1 stop5h 10m
Deal found 8/20![Delta logo]()
$399
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:00 am -
1 stop7h 46m
Wed 9/23:57 pm -
Nonstop3h 33m
Deal found 8/22![United Airlines logo]()
$499
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/286:00 am -
1 stop6h 08m
Thu 2/46:00 pm -
1 stop5h 10m
Deal found 8/20![Delta logo]()
$399
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/269:04 am -
2 stops13h 40m
Sun 10/48:45 am -
1 stop8h 56m
Deal found 8/20![United Airlines logo]()
$531
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:00 am -
1 stop7h 46m
Tue 9/112:17 pm -
Nonstop3h 31m
Deal found 8/22![United Airlines logo]()
$534
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/811:28 am -
1 stop7h 34m
Sat 12/126:06 pm -
1 stop5h 49m
Deal found 8/22![Delta logo]()
$458
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/77:30 am -
Nonstop3h 24m
Fri 9/113:57 pm -
Nonstop3h 33m
Deal found 8/22![United Airlines logo]()
$555
Last-minute flights from Chicago to Florida KeysDiscover last-minute flight deals from Chicago to Florida Keys. Data last updated August 23, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Florida Keys. Data last updated August 23, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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.
Fri 9/1112:54 pm -
1 stop8h 06m
Mon 9/145:34 pm -
1 stop7h 10m
Deal found 8/19![Frontier logo]()
$177
This American Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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.
Fri 9/115:29 pm -
Nonstop3h 16m
Mon 9/145:15 am -
Nonstop3h 33m
Deal found 8/18![American Airlines logo]()
$181
This American Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/122:30 pm -
Nonstop3h 17m
Mon 9/145:15 am -
Nonstop3h 33m
Deal found 8/20![American Airlines logo]()
$173
This American Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/122:30 pm -
Nonstop3h 17m
Sat 9/198:22 am -
Nonstop3h 28m
Deal found 8/22![American Airlines logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/121:06 pm -
1 stop7h 54m
Thu 9/174:30 pm -
1 stop8h 14m
Deal found 8/22![Frontier logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/121:04 pm -
1 stop7h 56m
Mon 9/145:50 am -
1 stop19h 33m
Deal found 8/20![Frontier logo]()
$180
This Trip.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:25 am -
1 stop9h 04m
Fri 9/185:34 pm -
1 stop7h 10m
Deal found 8/23![Frontier logo]()
$173
This Trip.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/146:25 am -
1 stop9h 04m
Thu 9/174:30 pm -
1 stop8h 14m
Deal found 8/18![Frontier logo]()
$178
This American Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/174:35 pm -
Nonstop3h 20m
Mon 9/215:15 am -
Nonstop3h 33m
Deal found 8/21![American Airlines logo]()
$172
This Trip.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/171:01 pm -
1 stop7h 59m
Mon 9/215:50 am -
1 stop19h 33m
Deal found 8/19![Frontier logo]()
$178
This Frontier deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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.
Fri 9/187:25 am -
1 stop11h 20m
Tue 9/222:37 pm -
1 stop6h 52m
Deal found 8/19![Frontier logo]()
$177
This Cheapflightsfares deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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.
Fri 9/251:01 pm -
1 stop7h 59m
Sat 9/267:23 am -
1 stop12h 04m
Deal found 8/18![Frontier logo]()
$175
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 August 23, 2026.
Search for one-way flight options from Chicago to Florida Keys. Find affordable one-way fares based on user searches. Data last updated August 23, 2026.
This American Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:05 am -
Nonstop3h 08m
Deal found 8/20![American Airlines logo]()
$87
This CheapOair deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1112:54 pm -
1 stop8h 06m
Deal found 8/20![Frontier logo]()
$87
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/121:06 pm -
1 stop7h 54m
Deal found 8/23![Frontier logo]()
$88
This Super.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/22:46 pm -
1 stop22h 53m
Deal found 8/21![Frontier logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:25 am -
1 stop7h 59m
Deal found 8/21![Frontier logo]()
$90
This Cheapflightsfares deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:00 am -
1 stop6h 33m
Deal found 8/20![Frontier logo]()
$91
This Frontier deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1912:03 pm -
1 stop5h 09m
Deal found 8/18![Frontier logo]()
$91
This Cheapflightsfares deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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.
Fri 9/1110:26 am -
1 stop9h 07m
Deal found 8/18![Frontier logo]()
$92
This CheapOair deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/261:06 pm -
1 stop7h 54m
Deal found 8/19![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:30 am -
1 stop17h 17m
Deal found 8/20![Frontier logo]()
$93
This Trip.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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.
Fri 10/3010:26 am -
1 stop10h 23m
Deal found 8/19![Frontier logo]()
$95
This American Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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.
Fri 9/117:00 pm -
Nonstop3h 15m
Deal found 8/18![American Airlines logo]()
$96
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 August 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $172 (American Airlines) |
One-way from | $87 (American Airlines) |
Popular in | July |
Cheapest in | January |
Average price | $300 |
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 7,457,451 searches. Data last updated August 23, 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 Chicago O'Hare Intl - MIA Miami
ORDMIA
Chicago O'Hare Intl
Wed 11/11
7:00 am-11:11 am
Nonstop3h 11m
Miami
Mon 11/23
7:00 am-2:12 pm
1 stop8h 12m
$191
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Sat 10/3
9:55 am-8:30 pm
1 stop9h 35m
Miami
Mon 10/5
6:40 am-8:45 am
Nonstop3h 05m
$197
ChicagoMiami
ORD Chicago O'Hare Intl - MIA Miami
ORDMIA
Chicago O'Hare Intl
Mon 11/16
9:53 am-3:55 pm
1 stop5h 02m
Miami
Thu 11/26
11:34 am-5:03 pm
1 stop6h 29m
$217
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Sat 12/12
4:19 pm-12:57 am
1 stop7h 38m
Miami
Wed 12/16
1:10 pm-6:04 pm
1 stop5h 54m
$248
Quickest round-trip
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Tue 12/15
1:25 pm-5:25 pm
Nonstop3h 00m
Miami
Wed 12/23
6:25 pm-8:45 pm
Nonstop3h 20m
$253
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Thu 10/15
1:27 pm-9:16 pm
1 stop6h 49m
Miami
Tue 10/20
6:20 pm-10:33 pm
1 stop5h 13m
$258
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Wed 9/23
12:50 pm-8:05 pm
2 stops6h 15m
Miami
Mon 9/28
7:15 am-9:20 am
Nonstop3h 05m
$268
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Sat 9/12
11:20 am-3:20 pm
Nonstop3h 00m
Miami
Sat 9/19
6:30 am-10:40 am
1 stop5h 10m
$269
ChicagoMiami
ORD Chicago O'Hare Intl - MIA Miami
ORDMIA
Chicago O'Hare Intl
Sat 10/17
7:25 am-11:50 am
Nonstop3h 25m
Miami
Wed 10/21
12:29 pm-3:00 pm
Nonstop3h 31m
$271
ChicagoMiami
ORD Chicago O'Hare Intl - MIA Miami
ORDMIA
Chicago O'Hare Intl
Tue 9/29
7:30 am-11:55 am
Nonstop3h 25m
Miami
Sat 10/3
7:00 am-12:54 pm
1 stop6h 54m
$281
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 $252). Flying from Chicago to Florida Keys in June is currently the most expensive (average of $380). 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 August 23, 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.
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 August 23, 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.
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
Find useful and relevant information for your journey from 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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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 August 23, 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 7,457,451 searches. Data last updated August 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$206 | Average$462 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$249 | Average$410 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$304 | Average$471 | FlexibilityNo cancel fee | On-time71% |