$47+ Cheap flights from Chicago (CHI) to Islamorada, FL
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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
May 19 — May 261
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Islamorada with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to Islamorada are usually found in September or October, booked 76 days in advance, depart on a Monday or Sunday and return on a Friday
Cheap flight deals from Chicago to Islamorada
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Best
Last-minute
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Cheapest flights from Chicago to IslamoradaExplore the most affordable flight options available from Chicago to Islamorada. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 19, 2026.
Explore the most affordable flight options available from Chicago to Islamorada. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 19, 2026.
This Priceline deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/267:50 am
ORD
- MIA
Nonstop3h 08m
Multiple Airlines
Sat 5/29:21 pm
MIA
- ORD
Nonstop3h 38m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 4/286:08 pm
ORD
- MIA
1 stop16h 55m
Frontier
Thu 4/309:21 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 4/14![Frontier logo]()
$108
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/711:23 am
MIA
- ORD
1 stop9h 28m
Frontier
Deal found 4/14![Frontier logo]()
$109
This WAYA deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/29:16 am
ORD
- MIA
1 stop5h 48m
Multiple Airlines
Thu 5/72:13 pm
MIA
- ORD
Nonstop3h 37m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/267:50 am
ORD
- MIA
Nonstop3h 08m
Multiple Airlines
Thu 4/309:21 pm
MIA
- ORD
Nonstop3h 38m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$111
This WAYA deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/25:50 am
ORD
- MIA
1 stop7h 25m
Frontier
Thu 5/72:13 pm
MIA
- ORD
Nonstop3h 37m
Frontier
Deal found 4/16![Frontier logo]()
$112
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/106:50 am
ORD
- MIA
1 stop8h 37m
Frontier
Thu 5/142:17 pm
MIA
- ORD
Nonstop3h 37m
Frontier
Deal found 4/14![Frontier logo]()
$113
This Spirit deal was found by Cheapflights users on 4/18. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/37:50 am
ORD
- MIA
Nonstop3h 08m
Spirit Airlines
Thu 5/79:30 pm
MIA
- ORD
Nonstop3h 26m
Spirit Airlines
Deal found 4/18![Spirit Airlines logo]()
$114
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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.
Sat 5/23:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Tue 5/511:23 am
MIA
- ORD
1 stop9h 28m
Frontier
Deal found 4/14![Frontier logo]()
$115
This Gotogate deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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.
Sun 5/311:28 am
ORD
- MIA
1 stop10h 03m
Multiple Airlines
Thu 5/72:13 pm
MIA
- ORD
Nonstop3h 37m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$116
This Mytrip deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:16 am
ORD
- MIA
1 stop5h 48m
Spirit Airlines
Thu 5/79:30 pm
MIA
- ORD
Nonstop3h 26m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
MDW
- MIA
1 stop5h 56m
Multiple Airlines
Sat 5/24:59 pm
MIA
- MDW
1 stop6h 15m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$136
Best flights from Chicago to IslamoradaDiscover carefully curated flight deals from Chicago to Islamorada that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 19, 2026.
Discover carefully curated flight deals from Chicago to Islamorada that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 19, 2026.
This United Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/137:14 am
ORD
- MIA
Nonstop3h 23m
United Airlines
Wed 5/207:40 pm
MIA
- ORD
Nonstop3h 40m
United Airlines
Deal found 4/15![United Airlines logo]()
$199
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/231:59 pm
MDW
- MIA
1 stop8h 12m
Delta
Tue 5/266:33 am
MIA
- MDW
1 stop7h 46m
Delta
Deal found 4/15![Delta logo]()
$243
This Southwest deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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
Thu 5/215:25 pm
MIA
- MDW
1 stop6h 20m
Southwest
Deal found 4/15![Southwest logo]()
$249
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/291:36 pm
ORD
- MIA
1 stop7h 14m
Delta
Fri 5/16:00 am
MIA
- ORD
1 stop5h 09m
Delta
Deal found 4/15![Delta logo]()
$245
This Southwest deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/138:15 am
MDW
- MIA
1 stop7h 35m
Southwest
Sun 5/176:45 am
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 4/14![Southwest logo]()
$288
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/510:35 am
ORD
- MIA
Nonstop3h 22m
United Airlines
Sat 5/96:10 pm
MIA
- ORD
1 stop6h 34m
United Airlines
Deal found 4/16![United Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/307:00 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Wed 6/34:53 pm
MIA
- ORD
1 stop8h 52m
United Airlines
Deal found 4/14![United Airlines logo]()
$311
This Southwest deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/303:45 pm
MDW
- MIA
Nonstop2h 55m
Southwest
Sat 6/67:15 am
MIA
- MDW
1 stop10h 50m
Southwest
Deal found 4/15![Southwest logo]()
$314
This United Airlines deal was found by Cheapflights users on 4/18. 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 5/277:00 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Sat 5/305:39 pm
MIA
- ORD
Nonstop3h 44m
United Airlines
Deal found 4/18![United Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 4/18. 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.
Wed 5/137:55 am
MDW
- MIA
Nonstop3h 00m
Southwest
Mon 5/186:20 am
MIA
- MDW
1 stop6h 40m
Southwest
Deal found 4/18![Southwest logo]()
$317
This United Airlines deal was found by Cheapflights users on 4/18. 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 6/36:00 am
ORD
- MIA
1 stop7h 38m
United Airlines
Tue 6/912:30 pm
MIA
- ORD
Nonstop3h 43m
United Airlines
Deal found 4/18![United Airlines logo]()
$323
This Southwest deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/188:10 am
MDW
- MIA
Nonstop3h 00m
Southwest
Wed 5/206:40 am
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 4/17![Southwest logo]()
$330
This United Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/277:00 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Sun 5/315:24 pm
MIA
- ORD
Nonstop3h 44m
United Airlines
Deal found 4/15![United Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 4/18. 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.
Tue 6/212:50 pm
MDW
- MIA
2 stops7h 20m
Southwest
Tue 6/911:45 am
MIA
- MDW
1 stop5h 10m
Southwest
Deal found 4/18![Southwest logo]()
$338
This United Airlines deal was found by Cheapflights users on 4/18. 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.
Tue 6/27:00 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Tue 6/94:53 pm
MIA
- ORD
1 stop8h 52m
United Airlines
Deal found 4/18![United Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 5/37:40 am
MDW
- MIA
Nonstop3h 00m
Southwest
Tue 5/53:00 pm
MIA
- MDW
1 stop7h 50m
Southwest
Deal found 4/17![Southwest logo]()
$367
This United Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 5/37:14 am
ORD
- MIA
Nonstop3h 23m
United Airlines
Tue 5/512:10 pm
MIA
- ORD
Nonstop3h 40m
United Airlines
Deal found 4/17![United Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 7/1411:45 am
MDW
- MIA
Nonstop3h 00m
Southwest
Fri 7/175:35 am
MIA
- MDW
1 stop5h 25m
Southwest
Deal found 4/17![Southwest logo]()
$370
This Southwest deal was found by Cheapflights users on 4/18. 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 6/64:50 pm
MDW
- MIA
1 stop5h 10m
Southwest
Thu 6/115:35 am
MIA
- MDW
2 stops8h 50m
Southwest
Deal found 4/18![Southwest logo]()
$371
This United Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/2110:40 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Mon 5/255:24 pm
MIA
- ORD
Nonstop3h 44m
United Airlines
Deal found 4/14![United Airlines logo]()
$383
This Southwest deal was found by Cheapflights users on 4/18. 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.
Wed 6/247:45 am
MDW
- MIA
2 stops7h 05m
Southwest
Tue 6/301:45 pm
MIA
- MDW
2 stops7h 05m
Southwest
Deal found 4/18![Southwest logo]()
$376
This United Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/1210:30 am
ORD
- MIA
1 stop6h 48m
United Airlines
Thu 5/146:10 pm
MIA
- ORD
1 stop6h 34m
United Airlines
Deal found 4/14![United Airlines logo]()
$387
This Southwest deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/222:10 pm
MDW
- MIA
2 stops7h 50m
Southwest
Tue 5/265:45 pm
MIA
- MDW
1 stop4h 40m
Southwest
Deal found 4/15![Southwest logo]()
$378
Last-minute flights from Chicago to IslamoradaDiscover last-minute flight deals from Chicago to Islamorada. Data last updated April 19, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Islamorada. Data last updated April 19, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/267:50 am
ORD
- MIA
Nonstop3h 08m
Multiple Airlines
Sat 5/29:21 pm
MIA
- ORD
Nonstop3h 38m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/267:50 am
ORD
- MIA
Nonstop3h 08m
Multiple Airlines
Thu 4/309:21 pm
MIA
- ORD
Nonstop3h 38m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 4/286:08 pm
ORD
- MIA
1 stop16h 55m
Frontier
Thu 4/309:21 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 4/14![Frontier logo]()
$108
This WAYA deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/29:16 am
ORD
- MIA
1 stop5h 48m
Multiple Airlines
Thu 5/72:13 pm
MIA
- ORD
Nonstop3h 37m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$110
This WAYA deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/25:50 am
ORD
- MIA
1 stop7h 25m
Frontier
Thu 5/72:13 pm
MIA
- ORD
Nonstop3h 37m
Frontier
Deal found 4/16![Frontier logo]()
$112
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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.
Sat 5/23:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Tue 5/511:23 am
MIA
- ORD
1 stop9h 28m
Frontier
Deal found 4/14![Frontier logo]()
$115
This Mytrip deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:16 am
ORD
- MIA
1 stop5h 48m
Spirit Airlines
Thu 5/79:30 pm
MIA
- ORD
Nonstop3h 26m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
MDW
- MIA
1 stop5h 56m
Multiple Airlines
Sat 5/24:59 pm
MIA
- MDW
1 stop6h 15m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$136
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/711:23 am
MIA
- ORD
1 stop9h 28m
Frontier
Deal found 4/14![Frontier logo]()
$109
This Spirit deal was found by Cheapflights users on 4/18. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/37:50 am
ORD
- MIA
Nonstop3h 08m
Spirit Airlines
Thu 5/79:30 pm
MIA
- ORD
Nonstop3h 26m
Spirit Airlines
Deal found 4/18![Spirit Airlines logo]()
$114
This Gotogate deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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.
Sun 5/311:28 am
ORD
- MIA
1 stop10h 03m
Multiple Airlines
Thu 5/72:13 pm
MIA
- ORD
Nonstop3h 37m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$116
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/106:50 am
ORD
- MIA
1 stop8h 37m
Frontier
Thu 5/142:17 pm
MIA
- ORD
Nonstop3h 37m
Frontier
Deal found 4/14![Frontier logo]()
$113
One-way flights from Chicago to IslamoradaSearch for one-way flight options from Chicago to Islamorada. Find affordable one-way fares based on user searches. Data last updated April 19, 2026.
Search for one-way flight options from Chicago to Islamorada. Find affordable one-way fares based on user searches. Data last updated April 19, 2026.
This Frontier deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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
Deal found 4/15![Frontier logo]()
$47
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/109:20 am
ORD
- MIA
Nonstop3h 08m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$49
This Spirit deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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.
Mon 5/259:20 am
ORD
- MIA
Nonstop3h 08m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$50
This Mytrip deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/319:20 am
ORD
- MIA
Nonstop3h 08m
Spirit Airlines
Deal found 4/16![Spirit Airlines logo]()
$51
This CheapOair deal was found by Cheapflights users on 4/19. 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.
Mon 5/49:20 am
ORD
- MIA
Nonstop3h 08m
Spirit Airlines
Deal found 4/19![Spirit Airlines logo]()
$54
This CheapOair deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/111:28 am
ORD
- MIA
1 stop10h 03m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$60
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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.
Fri 5/12:15 pm
MDW
- MIA
1 stop24h 49m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$67
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/144:05 pm
ORD
- MIA
1 stop7h 39m
Frontier
Deal found 4/14![Frontier logo]()
$68
This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/37:50 am
ORD
- MIA
Nonstop3h 08m
Spirit Airlines
Deal found 4/16![Spirit Airlines logo]()
$70
This Trip.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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.
Tue 5/196:00 am
MDW
- MIA
1 stop9h 27m
Frontier
Deal found 4/16![Frontier logo]()
$71
This Trip.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:00 am
MDW
- MIA
1 stop15h 47m
Frontier
Deal found 4/14![Frontier logo]()
$72
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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.
Fri 5/12:15 pm
MDW
- MIA
1 stop23h 00m
Frontier
Deal found 4/15![Frontier logo]()
$73
Find flight deals from Chicago to Islamorada
Keep the following information in mind while searching for Chicago to Islamorada flight deals. Data was last updated April 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $106 (Priceline) |
One-way from | $47 (Frontier) |
Popular in | December |
Cheapest in | September |
Average price | $268 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Islamorada 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 19, 2026.
Use the filters below to find and compare flights from Chicago to Islamorada that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 5/13
7:14 am-11:37 am
Nonstop3h 23m
Miami
Wed 5/20
7:40 pm-10:20 pm
Nonstop3h 40m
$199
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 5/23
1:59 pm-11:11 pm
1 stop8h 12m
Miami
Tue 5/26
6:33 am-1:19 pm
1 stop7h 46m
$243
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 4/29
1:36 pm-9:50 pm
1 stop7h 14m
Miami
Fri 5/1
6:00 am-10:09 am
1 stop5h 09m
$245
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Fri 5/15
6:50 pm-10:50 pm
Nonstop3h 00m
Miami
Thu 5/21
5:25 pm-10:45 pm
1 stop6h 20m
$249
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 5/13
8:15 am-4:50 pm
1 stop7h 35m
Miami
Sun 5/17
6:45 am-8:55 am
Nonstop3h 10m
$288
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Tue 5/5
10:35 am-2:57 pm
Nonstop3h 22m
Miami
Sat 5/9
6:10 pm-11:44 pm
1 stop6h 34m
$299
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Sat 5/30
7:00 am-11:24 am
Nonstop3h 24m
Miami
Wed 6/3
4:53 pm-12:45 am
1 stop8h 52m
$311
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 5/30
3:45 pm-7:40 pm
Nonstop2h 55m
Miami
Sat 6/6
7:15 am-5:05 pm
1 stop10h 50m
$314
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 5/27
7:00 am-11:24 am
Nonstop3h 24m
Miami
Sat 5/30
5:39 pm-8:23 pm
Nonstop3h 44m
$317
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 5/13
7:55 am-11:55 am
Nonstop3h 00m
Miami
Mon 5/18
6:20 am-12:00 pm
1 stop6h 40m
$317
Showing 1-10 of 45 resultsSorted by cheapest first
Best time to book a flight from Chicago to Islamorada
Have a flexible travel schedule? Discover the best time to fly to Islamorada from Chicago with our price prediction graph.
MDW-MIA
ORD-MIA
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 Islamorada
CHI-I5L
MDW-MIA
ORD-MIA
How far ahead should I book a flight from Chicago to Islamorada?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Islamorada. Price data was last updated on April 17, 2026.
The best time to book flights from Chicago to Islamorada is 76 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest time of day to fly from CHI to I5L?
Find hourly flight availability from Chicago to Islamorada. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 19, 2026.
When flying from Chicago to Islamorada, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 13% versus a flight in the afternoon.
What is the cheapest day to fly from Chicago to Islamorada?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Islamorada. Price data was last updated on April 11, 2026.
Travelers seeking maximum savings on their Chicago to Islamorada flight should consider departing on Wednesday at noon when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Islamorada
Explore weekly flight availability from Chicago to Islamorada. 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 19, 2026.
The most flights from CHI to I5L are scheduled on a Friday (60 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (35 on average).
How much does it cost to fly round-trip from Chicago to Islamorada?
Reviews of airlines servicing Islamorada
Get insights into the airlines that provide service to Islamorada. 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 Islamorada. Reviews last updated April 19, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican Airlines from Chicago to Islamorada. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
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 Islamorada. 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 Islamorada
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Complete your trip
Complete your trip to Islamorada by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Islamorada by cabin class
Find flights from Chicago to Islamorada, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Islamorada flights
Browse other Chicago and Islamorada flight options. Last updated on April 19, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on April 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 9 airlines flying from Chicago to Islamorada
Discover the top 9 airlines that operate flights from Chicago to Islamorada. 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 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$56 | Average$187 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$69 | Average$230 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$84 | Average$142 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$89 | Average$260 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$108 | Average$370 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$368 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$156 | Average$369 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$176 | Average$249 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$176 | Average$375 | FlexibilityNo cancel fee | On-time63% |