$92+ 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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Aug 31 — Sep 71
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 January or September, booked 65 days in advance, depart on a Monday or Saturday 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 August 1, 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 August 1, 2026.
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/269:25 am
MDW
- MIA
Nonstop3h 00m
Southwest
Sat 8/296:30 am
MIA
- MDW
1 stop5h 10m
Southwest
Deal found 7/30![Southwest logo]()
$177
This United Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 9/16:00 am
ORD
- MIA
1 stop7h 46m
United Airlines
Tue 9/812:17 pm
MIA
- ORD
Nonstop3h 31m
United Airlines
Deal found 7/30![United Airlines logo]()
$177
This Trip.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 10/1412:03 pm
MDW
- MIA
1 stop5h 19m
Frontier
Tue 10/276:45 am
MIA
- MDW
1 stop5h 13m
Frontier
Deal found 7/31![Frontier logo]()
$178
This Cheapflightsfares deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/196:30 am
ORD
- MIA
1 stop17h 16m
Frontier
Mon 9/215:50 am
MIA
- ORD
1 stop19h 33m
Frontier
Deal found 7/31![Frontier logo]()
$178
This Mytrip deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/1912:56 pm
ORD
- MIA
1 stop23h 46m
Frontier
Thu 9/246:46 pm
MIA
- ORD
1 stop6h 59m
Frontier
Deal found 7/31![Frontier logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 9/177:25 am
ORD
- MIA
1 stop7h 18m
Frontier
Mon 9/219:30 pm
MIA
- ORD
1 stop15h 21m
Frontier
Deal found 7/30![Frontier logo]()
$180
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/107:55 am
MDW
- MIA
1 stop7h 15m
Southwest
Mon 9/147:15 am
MIA
- MDW
Nonstop3h 05m
Southwest
Deal found 7/29![Southwest logo]()
$181
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/117:30 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Mon 9/143:57 pm
MIA
- ORD
Nonstop3h 33m
United Airlines
Deal found 7/31![United Airlines logo]()
$181
This Priceline deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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.
Thu 11/127:25 am
MDW
- MIA
1 stop9h 47m
Frontier
Mon 11/166:45 am
MIA
- MDW
1 stop5h 13m
Frontier
Deal found 7/30![Frontier logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/187:10 am
ORD
- MIA
1 stop8h 11m
Frontier
Thu 8/209:48 pm
MIA
- ORD
1 stop26h 39m
Frontier
Deal found 7/30![Frontier logo]()
$182
This Cheapflightsfares deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 10/157:00 am
ORD
- MIA
1 stop12h 33m
Frontier
Mon 10/192:23 pm
MIA
- ORD
1 stop23h 09m
Frontier
Deal found 7/30![Frontier logo]()
$183
This Super.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/2112:44 am
ORD
- MIA
1 stop8h 31m
Frontier
Sat 8/223:07 pm
MIA
- ORD
1 stop6h 01m
Frontier
Deal found 7/30![Frontier logo]()
$184
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 August 1, 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 August 1, 2026.
This United Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 10/213:00 pm
ORD
- MIA
1 stop7h 44m
United Airlines
Mon 10/269:00 am
MIA
- ORD
Nonstop3h 34m
United Airlines
Deal found 7/29![United Airlines logo]()
$191
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/92:05 pm
MDW
- MIA
1 stop6h 50m
Southwest
Mon 9/147:15 am
MIA
- MDW
Nonstop3h 05m
Southwest
Deal found 7/29![Southwest logo]()
$191
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:10 pm
MDW
- MIA
1 stop6h 57m
Delta
Tue 8/2510:35 am
MIA
- MDW
1 stop6h 40m
Delta
Deal found 7/31![Delta logo]()
$286
This Southwest deal was found by Cheapflights users on 7/27. 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.
Mon 9/75:55 am
MDW
- MIA
1 stop4h 55m
Southwest
Thu 9/104:50 pm
MIA
- MDW
2 stops6h 35m
Southwest
Deal found 7/27![Southwest logo]()
$196
This United Airlines deal was found by Cheapflights users on 7/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:05 am
ORD
- MIA
1 stop6h 41m
United Airlines
Thu 9/175:37 pm
MIA
- ORD
1 stop7h 51m
United Airlines
Deal found 7/28![United Airlines logo]()
$211
This Southwest deal was found by Cheapflights users on 7/28. 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 9/113:20 pm
MDW
- MIA
1 stop4h 30m
Southwest
Mon 9/147:15 am
MIA
- MDW
Nonstop3h 05m
Southwest
Deal found 7/28![Southwest logo]()
$196
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/1911:45 am
MDW
- MIA
2 stops7h 35m
Southwest
Thu 9/246:25 pm
MIA
- MDW
1 stop5h 00m
Southwest
Deal found 7/31![Southwest logo]()
$216
This United Airlines deal was found by Cheapflights users on 7/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/247:30 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Wed 8/263:57 pm
MIA
- ORD
Nonstop3h 33m
United Airlines
Deal found 7/27![United Airlines logo]()
$261
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/81:00 pm
MDW
- MIA
2 stops6h 15m
Southwest
Tue 9/152:20 pm
MIA
- MDW
2 stops9h 35m
Southwest
Deal found 7/31![Southwest logo]()
$221
This United Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 9/810:30 am
ORD
- MIA
Nonstop3h 21m
United Airlines
Thu 9/103:57 pm
MIA
- ORD
Nonstop3h 33m
United Airlines
Deal found 7/30![United Airlines logo]()
$261
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:32 am
ORD
- MIA
Nonstop3h 22m
United Airlines
Sun 9/612:17 pm
MIA
- ORD
Nonstop3h 31m
United Airlines
Deal found 7/31![United Airlines logo]()
$269
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 10/312:10 pm
MDW
- MIA
Nonstop3h 10m
Southwest
Tue 10/612:35 pm
MIA
- MDW
Nonstop3h 05m
Southwest
Deal found 7/30![Southwest logo]()
$253
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/810:30 am
ORD
- MIA
Nonstop3h 21m
United Airlines
Mon 9/1412:17 pm
MIA
- ORD
Nonstop3h 31m
United Airlines
Deal found 7/31![United Airlines logo]()
$281
This Southwest deal was found by Cheapflights users on 8/1. 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.
Thu 8/278:00 am
MDW
- MIA
Nonstop3h 10m
Southwest
Sat 8/296:30 am
MIA
- MDW
1 stop5h 10m
Southwest
Deal found 8/1![Southwest logo]()
$269
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1010:30 am
ORD
- MIA
Nonstop3h 21m
United Airlines
Mon 9/143:57 pm
MIA
- ORD
Nonstop3h 33m
United Airlines
Deal found 7/31![United Airlines logo]()
$285
This United Airlines deal was found by Cheapflights users on 7/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/302:27 pm
ORD
- MIA
Nonstop3h 22m
United Airlines
Sun 11/89:00 am
MIA
- ORD
Nonstop3h 34m
United Airlines
Deal found 7/28![United Airlines logo]()
$321
This Southwest deal was found by Cheapflights users on 8/1. 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 9/2611:45 am
MDW
- MIA
2 stops7h 35m
Southwest
Mon 9/284:50 pm
MIA
- MDW
2 stops6h 35m
Southwest
Deal found 8/1![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 7/28. 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.
Sat 8/159:05 am
MDW
- MIA
2 stops9h 10m
Southwest
Tue 8/187:30 am
MIA
- MDW
2 stops8h 55m
Southwest
Deal found 7/28![Southwest logo]()
$323
This Southwest deal was found by Cheapflights users on 7/27. 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 8/239:00 am
MDW
- MIA
Nonstop3h 05m
Southwest
Thu 8/277:15 am
MIA
- MDW
Nonstop3h 05m
Southwest
Deal found 7/27![Southwest logo]()
$335
This Southwest deal was found by Cheapflights users on 7/28. 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 9/118:00 am
MDW
- MIA
Nonstop3h 10m
Southwest
Fri 9/187:15 am
MIA
- MDW
Nonstop3h 05m
Southwest
Deal found 7/28![Southwest logo]()
$335
This United Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/107:00 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Sat 9/511:30 am
MIA
- ORD
1 stop9h 35m
United Airlines
Deal found 7/29![United Airlines logo]()
$407
This United Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:00 am
ORD
- MIA
1 stop8h 46m
United Airlines
Thu 8/203:57 pm
MIA
- ORD
Nonstop3h 33m
United Airlines
Deal found 7/29![United Airlines logo]()
$417
Last-minute flights from Chicago to IslamoradaDiscover last-minute flight deals from Chicago to Islamorada. Data last updated August 1, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Islamorada. Data last updated August 1, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/187:10 am
ORD
- MIA
1 stop8h 11m
Frontier
Thu 8/209:48 pm
MIA
- ORD
1 stop26h 39m
Frontier
Deal found 7/30![Frontier logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 8/1. 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.
Tue 8/181:59 pm
ORD
- MIA
1 stop8h 06m
Frontier
Wed 8/1911:10 am
MIA
- ORD
1 stop9h 58m
Frontier
Deal found 8/1![Frontier logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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.
Wed 8/191:59 pm
ORD
- MIA
1 stop8h 06m
Frontier
Wed 8/268:00 am
MIA
- ORD
1 stop8h 59m
Frontier
Deal found 7/30![Frontier logo]()
$179
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/199:25 am
MDW
- MIA
Nonstop3h 00m
Southwest
Mon 8/247:15 am
MIA
- MDW
Nonstop3h 05m
Southwest
Deal found 7/29![Southwest logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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.
Wed 8/191:59 pm
ORD
- MIA
1 stop8h 06m
Frontier
Mon 8/248:10 am
MIA
- ORD
1 stop12h 49m
Frontier
Deal found 7/30![Frontier logo]()
$185
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/198:15 am
MDW
- MIA
2 stops6h 15m
Southwest
Thu 8/207:15 am
MIA
- MDW
Nonstop3h 05m
Southwest
Deal found 7/29![Southwest logo]()
$186
This Kissandfly.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:30 am
ORD
- MIA
Nonstop3h 24m
Frontier
Mon 8/248:10 am
MIA
- ORD
1 stop12h 49m
Frontier
Deal found 7/30![Frontier logo]()
$178
This Super.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/2112:44 am
ORD
- MIA
1 stop8h 31m
Frontier
Sat 8/223:07 pm
MIA
- ORD
1 stop6h 01m
Frontier
Deal found 7/30![Frontier logo]()
$184
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/221:59 pm
ORD
- MIA
1 stop5h 30m
Frontier
Mon 8/318:10 am
MIA
- ORD
1 stop12h 49m
Frontier
Deal found 7/31![Frontier logo]()
$186
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/269:25 am
MDW
- MIA
Nonstop3h 00m
Southwest
Sat 8/296:30 am
MIA
- MDW
1 stop5h 10m
Southwest
Deal found 7/30![Southwest logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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.
Wed 8/261:59 pm
ORD
- MIA
1 stop8h 06m
Frontier
Fri 8/2811:10 am
MIA
- ORD
1 stop9h 49m
Frontier
Deal found 7/30![Frontier logo]()
$187
This American Airlines deal was found by Cheapflights users on 8/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:59 pm
ORD
- MIA
Nonstop3h 18m
American Airlines
Sat 9/58:59 pm
MIA
- ORD
Nonstop3h 31m
American Airlines
Deal found 8/1![American Airlines logo]()
$181
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 August 1, 2026.
Search for one-way flight options from Chicago to Islamorada. Find affordable one-way fares based on user searches. Data last updated August 1, 2026.
This Frontier deal was found by Cheapflights users on 8/1. 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.
Mon 9/286:25 am
MDW
- MIA
1 stop9h 04m
Frontier
Deal found 8/1![Frontier logo]()
$92
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 10/157:00 am
ORD
- MIA
1 stop12h 33m
Frontier
Deal found 7/31![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/181:59 pm
ORD
- MIA
1 stop22h 33m
Frontier
Deal found 7/30![Frontier logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 9/176:30 am
ORD
- MIA
1 stop13h 03m
Frontier
Deal found 7/30![Frontier logo]()
$94
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/308:55 am
MDW
- MIA
1 stop5h 35m
Southwest
Deal found 7/29![Southwest logo]()
$96
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/247:30 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Deal found 7/31![United Airlines logo]()
$96
This American Airlines deal was found by Cheapflights users on 8/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/155:29 pm
ORD
- MIA
Nonstop3h 16m
American Airlines
Deal found 8/1![American Airlines logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/1811:50 am
MDW
- MIA
1 stop24h 42m
Frontier
Deal found 7/30![Frontier logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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.
Wed 8/197:05 am
ORD
- MIA
1 stop8h 16m
Frontier
Deal found 7/30![Frontier logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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.
Wed 9/166:30 am
ORD
- MIA
1 stop17h 16m
Frontier
Deal found 7/31![Frontier logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/112:46 pm
ORD
- MIA
1 stop22h 53m
Frontier
Deal found 7/29![Frontier logo]()
$103
This Trip.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/281:59 pm
ORD
- MIA
1 stop8h 06m
Frontier
Deal found 7/30![Frontier logo]()
$104
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 August 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $177 (Southwest) |
One-way from | $92 (Frontier) |
Popular in | July |
Cheapest in | January |
Average price | $294 |
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 August 1, 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 10/21
3:00 pm-11:44 pm
1 stop7h 44m
Miami
Mon 10/26
9:00 am-11:34 am
Nonstop3h 34m
$191
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 9/9
2:05 pm-9:55 pm
1 stop6h 50m
Miami
Mon 9/14
7:15 am-9:20 am
Nonstop3h 05m
$191
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Mon 9/7
5:55 am-11:50 am
1 stop4h 55m
Miami
Thu 9/10
4:50 pm-10:25 pm
2 stops6h 35m
$196
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Fri 9/11
3:20 pm-8:50 pm
1 stop4h 30m
Miami
Mon 9/14
7:15 am-9:20 am
Nonstop3h 05m
$196
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 9/16
7:05 am-2:46 pm
1 stop6h 41m
Miami
Thu 9/17
5:37 pm-12:28 am
1 stop7h 51m
$211
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 9/19
11:45 am-8:20 pm
2 stops7h 35m
Miami
Thu 9/24
6:25 pm-10:25 pm
1 stop5h 00m
$216
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 9/8
1:00 pm-8:15 pm
2 stops6h 15m
Miami
Tue 9/15
2:20 pm-10:55 pm
2 stops9h 35m
$221
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 10/3
12:10 pm-4:20 pm
Nonstop3h 10m
Miami
Tue 10/6
12:35 pm-2:40 pm
Nonstop3h 05m
$253
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Mon 8/24
7:30 am-11:54 am
Nonstop3h 24m
Miami
Wed 8/26
3:57 pm-6:30 pm
Nonstop3h 33m
$261
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Tue 9/8
10:30 am-2:51 pm
Nonstop3h 21m
Miami
Thu 9/10
3:57 pm-6:30 pm
Nonstop3h 33m
$261
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
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 August 1, 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 at noon, which can drop the price by up to 13% versus a flight in the evening.
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 August 1, 2026.
The most flights from CHI to I5L are scheduled on a Friday (55 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (13 on average).
How much does it cost to fly round-trip from Chicago to Islamorada?
Airfare is below average for this route at the moment.
Chicago to Islamorada flights typically cost between $214 and $374 in August.The cheapest round-trip price found within the last 5 days was $177 on Southwest (Aug 26-Aug 29).
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 August 1, 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. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
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 August 1, 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.
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
Find useful and relevant information for your journey from Chicago to 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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Complete your trip
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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 August 1, 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 August 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 7 airlines flying from Chicago to Islamorada
Discover the top 7 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 August 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$56 | Average$206 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$84 | Average$130 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$89 | Average$243 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$108 | Average$374 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$157 | Average$378 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$160 | Average$365 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$195 | Average$384 | FlexibilityNo cancel fee | On-time63% |