$45+ 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 3/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Apr 1 — Apr 81
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 January, booked 86 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 March 2, 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 March 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 4/183:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Mon 4/2010:17 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 2/26![Frontier logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 4/254:28 pm
ORD
- MIA
1 stop7h 21m
Frontier
Thu 4/309:21 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 2/26![Frontier logo]()
$92
This CheapOair deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 4/256:34 pm
ORD
- MIA
Nonstop3h 08m
Multiple Airlines
Thu 4/309:21 pm
MIA
- ORD
Nonstop3h 38m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:18 am
ORD
- MIA
Nonstop3h 18m
Multiple Airlines
Fri 3/1312:45 pm
MIA
- ORD
Nonstop3h 38m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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
Wed 4/297:04 pm
MIA
- ORD
1 stop28h 35m
Frontier
Deal found 2/26![Frontier logo]()
$95
This Expedia deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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.
Mon 3/97:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Tue 3/107:12 am
MIA
- ORD
Nonstop3h 27m
Spirit Airlines
Deal found 2/26![Spirit Airlines logo]()
$96
This Super.com deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 3/99:05 pm
ORD
- MIA
Nonstop3h 15m
Frontier
Fri 3/1312:45 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 2/26![Frontier logo]()
$97
This Cheapflightsfares deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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.
Mon 3/97:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Fri 3/136:00 am
MIA
- ORD
Nonstop3h 25m
Spirit Airlines
Deal found 2/26![Spirit Airlines logo]()
$98
This CheapOair deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 5/23:52 pm
ORD
- MIA
Nonstop3h 19m
Multiple Airlines
Sat 5/97:00 am
MIA
- ORD
1 stop8h 20m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$99
This Frontier deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:00 am
MDW
- MIA
Nonstop3h 13m
Frontier
Sat 3/1411:13 am
MIA
- MDW
Nonstop3h 28m
Frontier
Deal found 3/1![Frontier logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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.
Mon 3/1610:55 am
ORD
- MIA
Nonstop3h 05m
Spirit Airlines
Thu 3/196:00 am
MIA
- ORD
Nonstop3h 25m
Spirit Airlines
Deal found 2/26![Spirit Airlines logo]()
$100
This Frontier deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Fri 4/1011:35 am
MIA
- MDW
Nonstop3h 26m
Frontier
Deal found 3/2![Frontier logo]()
$100
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 March 2, 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 March 2, 2026.
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/138:15 am
MDW
- MIA
1 stop7h 35m
Southwest
Mon 5/186:05 am
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 2/27![Southwest logo]()
$242
This Delta deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/16:07 pm
MDW
- MIA
1 stop5h 45m
Delta
Tue 4/146:00 am
MIA
- MDW
1 stop7h 07m
Delta
Deal found 3/1![Delta logo]()
$252
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/316:07 pm
MDW
- MIA
1 stop5h 45m
Delta
Tue 4/74:44 pm
MIA
- MDW
1 stop6h 47m
Delta
Deal found 2/28![Delta logo]()
$288
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:50 pm
MDW
- MIA
Nonstop3h 00m
Southwest
Tue 4/216:40 am
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 3/1![Southwest logo]()
$290
This Southwest deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/177:40 am
MDW
- MIA
Nonstop3h 00m
Southwest
Sat 3/216:25 am
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 2/28![Southwest logo]()
$321
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/316:07 pm
MDW
- MIA
1 stop5h 45m
Delta
Fri 4/36:00 am
MIA
- MDW
1 stop4h 56m
Delta
Deal found 2/28![Delta logo]()
$328
This United Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/278:52 am
ORD
- MIA
Nonstop3h 23m
United Airlines
Tue 4/712:24 pm
MIA
- ORD
Nonstop3h 39m
United Airlines
Deal found 3/1![United Airlines logo]()
$739
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/233:45 pm
MDW
- MIA
Nonstop2h 55m
Southwest
Tue 5/266:40 am
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 3/1![Southwest logo]()
$362
This Delta deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/317:10 am
ORD
- MIA
2 stops14h 16m
Delta
Sat 4/46:00 am
MIA
- ORD
1 stop5h 06m
Delta
Deal found 2/26![Delta logo]()
$363
This Southwest deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:50 pm
MDW
- MIA
Nonstop3h 00m
Southwest
Mon 4/137:15 pm
MIA
- MDW
1 stop5h 15m
Southwest
Deal found 2/26![Southwest logo]()
$370
This Delta deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/305:59 pm
ORD
- MIA
1 stop5h 53m
Delta
Fri 4/36:00 am
MIA
- ORD
1 stop4h 59m
Delta
Deal found 3/1![Delta logo]()
$408
This Southwest deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:55 am
ORD
- MIA
2 stops14h 15m
Southwest
Thu 6/45:55 am
MIA
- ORD
2 stops8h 35m
Southwest
Deal found 2/28![Southwest logo]()
$385
This Delta deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/306:07 pm
MDW
- MIA
1 stop5h 45m
Delta
Fri 4/36:00 am
MIA
- MDW
1 stop4h 56m
Delta
Deal found 3/2![Delta logo]()
$408
This Southwest deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:10 pm
MDW
- MIA
2 stops7h 50m
Southwest
Mon 4/206:40 am
MIA
- MDW
2 stops7h 30m
Southwest
Deal found 2/28![Southwest logo]()
$395
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/177:45 am
MDW
- MIA
1 stop4h 25m
Southwest
Sun 5/247:20 am
MIA
- MDW
2 stops8h 55m
Southwest
Deal found 2/27![Southwest logo]()
$395
This Delta deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/279:50 am
ORD
- MIA
1 stop6h 31m
Delta
Sat 4/46:00 am
MIA
- ORD
1 stop5h 06m
Delta
Deal found 2/26![Delta logo]()
$469
This Southwest deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/173:05 pm
ORD
- MIA
2 stops16h 45m
Southwest
Sun 4/196:10 am
MIA
- ORD
2 stops7h 40m
Southwest
Deal found 2/26![Southwest logo]()
$398
This Southwest deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 5/247:35 pm
ORD
- MIA
2 stops17h 55m
Southwest
Fri 5/296:20 am
MIA
- ORD
2 stops7h 30m
Southwest
Deal found 2/26![Southwest logo]()
$413
This Southwest deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 3/317:35 pm
ORD
- MIA
2 stops17h 50m
Southwest
Fri 4/36:15 am
MIA
- ORD
2 stops7h 35m
Southwest
Deal found 2/26![Southwest logo]()
$517
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/225:19 pm
ORD
- MIA
1 stop5h 22m
Delta
Sat 5/307:12 am
MIA
- ORD
2 stops10h 17m
Delta
Deal found 2/28![Delta logo]()
$772
This Delta deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/279:10 am
ORD
- MIA
1 stop7h 31m
Delta
Sun 5/316:00 am
MIA
- ORD
2 stops8h 01m
Delta
Deal found 3/1![Delta logo]()
$790
This Delta deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/142:05 pm
ORD
- MIA
1 stop6h 13m
Delta
Fri 3/207:40 am
MIA
- ORD
2 stops10h 03m
Delta
Deal found 2/27![Delta logo]()
$836
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:00 am
ORD
- MIA
2 stops16h 00m
Southwest
Sun 3/86:45 am
MIA
- ORD
2 stops16h 10m
Southwest
Deal found 2/27![Southwest logo]()
$779
Last-minute flights from Chicago to IslamoradaDiscover last-minute flight deals from Chicago to Islamorada. Data last updated March 2, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Islamorada. Data last updated March 2, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:18 am
ORD
- MIA
Nonstop3h 18m
Multiple Airlines
Fri 3/61:00 pm
MIA
- ORD
Nonstop3h 38m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:18 am
ORD
- MIA
Nonstop3h 18m
Multiple Airlines
Fri 3/1312:45 pm
MIA
- ORD
Nonstop3h 38m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/211:33 am
ORD
- MIA
Nonstop3h 15m
Multiple Airlines
Wed 3/117:12 am
MIA
- ORD
Nonstop3h 27m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$95
This Frontier deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:00 am
MDW
- MIA
Nonstop3h 13m
Frontier
Sat 3/1411:13 am
MIA
- MDW
Nonstop3h 28m
Frontier
Deal found 3/1![Frontier logo]()
$99
This Expedia deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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.
Mon 3/97:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Tue 3/107:12 am
MIA
- ORD
Nonstop3h 27m
Spirit Airlines
Deal found 2/26![Spirit Airlines logo]()
$96
This Super.com deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 3/99:05 pm
ORD
- MIA
Nonstop3h 15m
Frontier
Fri 3/1312:45 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 2/26![Frontier logo]()
$97
This Cheapflightsfares deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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.
Mon 3/97:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Fri 3/136:00 am
MIA
- ORD
Nonstop3h 25m
Spirit Airlines
Deal found 2/26![Spirit Airlines logo]()
$98
This Cheapflightsfares deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Sat 3/146:00 am
MIA
- ORD
Nonstop3h 25m
Spirit Airlines
Deal found 3/2![Spirit Airlines logo]()
$99
This Frontier deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/96:00 am
MDW
- MIA
Nonstop3h 13m
Frontier
Sat 3/1411:13 am
MIA
- MDW
Nonstop3h 28m
Frontier
Deal found 2/28![Frontier logo]()
$104
This Cheapflightsfares deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/107:25 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Sat 3/144:06 pm
MIA
- ORD
Nonstop3h 25m
Spirit Airlines
Deal found 2/27![Spirit Airlines logo]()
$103
This Super.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/156:00 am
MDW
- MIA
Nonstop3h 13m
Frontier
Thu 3/1911:13 am
MIA
- MDW
Nonstop3h 28m
Frontier
Deal found 2/28![Frontier logo]()
$103
This Cheapflightsfares deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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.
Mon 3/1610:55 am
ORD
- MIA
Nonstop3h 05m
Spirit Airlines
Thu 3/196:00 am
MIA
- ORD
Nonstop3h 25m
Spirit Airlines
Deal found 2/26![Spirit Airlines logo]()
$100
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 March 2, 2026.
Search for one-way flight options from Chicago to Islamorada. Find affordable one-way fares based on user searches. Data last updated March 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/244:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Deal found 2/26![Spirit Airlines logo]()
$45
This Gotogate deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Deal found 2/28![Spirit Airlines logo]()
$46
This Booking.com deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/96:00 am
MDW
- MIA
Nonstop3h 13m
Frontier
Deal found 2/27![Frontier logo]()
$49
This CheapOair deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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.
Tue 3/107:25 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Deal found 2/26![Spirit Airlines logo]()
$49
This CheapOair deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/174:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Deal found 2/27![Spirit Airlines logo]()
$50
This CheapOair deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/183:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Deal found 2/27![Frontier logo]()
$52
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/301:15 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Deal found 3/1![Frontier logo]()
$54
This Super.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Deal found 3/1![Frontier logo]()
$59
This Super.com deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 4/34:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Deal found 2/26![Spirit Airlines logo]()
$59
This Booking.com deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 4/66:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Deal found 2/26![Frontier logo]()
$60
This CheapOair deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 4/186:40 am
ORD
- MIA
Nonstop3h 02m
Spirit Airlines
Deal found 2/26![Spirit Airlines logo]()
$60
This Trip.com deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/212:15 pm
MDW
- MIA
1 stop9h 34m
Frontier
Deal found 2/27![Frontier logo]()
$61
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 March 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $91 (Kiwi.com) |
One-way from | $45 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $303 |
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 March 2, 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
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 5/13
8:15 am-4:50 pm
1 stop7h 35m
Miami
Mon 5/18
6:05 am-8:20 am
Nonstop3h 15m
$242
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 4/1
6:07 pm-12:52 am
1 stop5h 45m
Miami
Tue 4/14
6:00 am-12:07 pm
1 stop7h 07m
$252
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 3/31
6:07 pm-12:52 am
1 stop5h 45m
Miami
Tue 4/7
4:44 pm-10:31 pm
1 stop6h 47m
$288
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Fri 4/17
6:50 pm-10:50 pm
Nonstop3h 00m
Miami
Tue 4/21
6:40 am-8:50 am
Nonstop3h 10m
$290
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 3/17
7:40 am-11:40 am
Nonstop3h 00m
Miami
Sat 3/21
6:25 am-8:40 am
Nonstop3h 15m
$321
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 3/31
6:07 pm-12:52 am
1 stop5h 45m
Miami
Fri 4/3
6:00 am-9:56 am
1 stop4h 56m
$328
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 5/23
3:45 pm-7:40 pm
Nonstop2h 55m
Miami
Tue 5/26
6:40 am-8:50 am
Nonstop3h 10m
$362
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Tue 3/31
7:10 am-10:26 pm
2 stops14h 16m
Miami
Sat 4/4
6:00 am-10:06 am
1 stop5h 06m
$363
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Thu 4/9
6:50 pm-10:50 pm
Nonstop3h 00m
Miami
Mon 4/13
7:15 pm-11:30 pm
1 stop5h 15m
$370
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 5/27
5:55 am-9:10 pm
2 stops14h 15m
Miami
Thu 6/4
5:55 am-1:30 pm
2 stops8h 35m
$385
Showing 1-10 of 47 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.
ORD-MIA
MDW-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
ORD-MIA
MDW-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 February 27, 2026.
The best time to book flights from Chicago to Islamorada is 86 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 month to book a flight from Chicago to Islamorada?
Currently, October is the cheapest month in which you can book a flight from Chicago to Islamorada (average of $49). Flying from Chicago to Islamorada in July is currently the most expensive (average of $118). 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 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 March 2, 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 14% 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 February 21, 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 March 2, 2026.
The most flights from CHI to I5L are scheduled on a Sunday (60 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (26 on average).
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 March 2, 2026.
Read reviews from past customers who have flown Southwest, United Airlines, and American 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.
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Overall
8.0
Food
7.0
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 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 March 2, 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 March 2, 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 March 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$39 | Average$177 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$65 | Average$230 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$69 | Average$225 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$84 | Average$149 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$108 | Average$372 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$379 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$156 | Average$349 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$166 | Average$365 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$176 | Average$249 | FlexibilityNo cancel fee | On-time75% |