$95+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Jul 4 — Jul 111
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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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 June 4, 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 June 4, 2026.
This Frontier deal was found by Cheapflights users on 5/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:00 am
MDW
- MIA
1 stop9h 31m
Frontier
Wed 9/211:19 am
MIA
- MDW
1 stop11h 52m
Frontier
Deal found 5/30![Frontier logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 9/92:03 pm
ORD
- MIA
1 stop6h 01m
Frontier
Mon 9/146:45 am
MIA
- ORD
1 stop6h 17m
Frontier
Deal found 6/3![Frontier logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/147:05 am
ORD
- MIA
1 stop5h 48m
Frontier
Tue 7/218:30 am
MIA
- ORD
1 stop24h 23m
Frontier
Deal found 6/3![Frontier logo]()
$207
This Frontier deal was found by Cheapflights users on 5/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:00 am
MDW
- MIA
1 stop9h 31m
Frontier
Wed 9/166:45 am
MIA
- MDW
1 stop5h 13m
Frontier
Deal found 5/30![Frontier logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 8/1211:06 am
MDW
- MIA
1 stop5h 41m
Frontier
Mon 8/176:42 pm
MIA
- MDW
1 stop17h 30m
Frontier
Deal found 6/3![Frontier logo]()
$214
This Frontier deal was found by Cheapflights users on 5/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:00 am
MDW
- MIA
1 stop9h 31m
Frontier
Thu 9/106:45 am
MIA
- MDW
1 stop5h 13m
Frontier
Deal found 5/30![Frontier logo]()
$218
This Trip.com deal was found by Cheapflights users on 6/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1712:11 pm
MDW
- MIA
1 stop9h 54m
Frontier
Wed 8/195:26 pm
MIA
- MDW
1 stop5h 45m
Frontier
Deal found 6/1![Frontier logo]()
$221
This Orbitz deal was found by Cheapflights users on 5/31. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/112:11 pm
MDW
- MIA
1 stop7h 18m
Frontier
Tue 8/45:28 pm
MIA
- MDW
1 stop5h 35m
Frontier
Deal found 5/31![Frontier logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 10/12:03 pm
ORD
- MIA
1 stop6h 01m
Frontier
Mon 10/56:45 am
MIA
- ORD
1 stop6h 17m
Frontier
Deal found 6/3![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/1412:44 am
ORD
- MIA
1 stop8h 31m
Frontier
Thu 8/206:00 am
MIA
- ORD
1 stop11h 10m
Frontier
Deal found 6/3![Frontier logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 8/46:05 am
MDW
- MIA
1 stop6h 48m
Frontier
Wed 8/56:42 pm
MIA
- MDW
1 stop16h 09m
Frontier
Deal found 6/3![Frontier logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 8/47:05 am
ORD
- MIA
1 stop5h 48m
Frontier
Sat 8/88:30 am
MIA
- ORD
1 stop12h 23m
Frontier
Deal found 6/3![Frontier logo]()
$225
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 June 4, 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 June 4, 2026.
This Southwest deal was found by Cheapflights users on 5/31. 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.
Wed 7/155:35 am
MDW
- MIA
1 stop8h 35m
Southwest
Wed 7/224:00 pm
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 5/31![Southwest logo]()
$249
This United Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/226:05 pm
ORD
- MIA
Nonstop3h 22m
United Airlines
Tue 7/284:53 pm
MIA
- ORD
1 stop8h 52m
United Airlines
Deal found 6/3![United Airlines logo]()
$286
This United Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 9/17:30 am
ORD
- MIA
1 stop7h 25m
United Airlines
Sun 9/64:13 pm
MIA
- ORD
Nonstop3h 33m
United Airlines
Deal found 6/3![United Airlines logo]()
$288
This Southwest deal was found by Cheapflights users on 6/1. 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.
Wed 7/83:00 pm
MDW
- MIA
2 stops6h 15m
Southwest
Wed 7/2211:25 am
MIA
- MDW
2 stops8h 40m
Southwest
Deal found 6/1![Southwest logo]()
$308
This United Airlines deal was found by Cheapflights users on 6/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/176:05 pm
ORD
- MIA
Nonstop3h 22m
United Airlines
Wed 6/244:06 pm
MIA
- ORD
Nonstop3h 43m
United Airlines
Deal found 6/2![United Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/83:00 pm
MDW
- MIA
2 stops6h 15m
Southwest
Sat 7/117:15 am
MIA
- MDW
1 stop10h 50m
Southwest
Deal found 6/3![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/1011:00 am
MDW
- MIA
1 stop4h 25m
Southwest
Tue 7/144:00 pm
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 6/3![Southwest logo]()
$327
This United Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/296:05 pm
ORD
- MIA
Nonstop3h 22m
United Airlines
Mon 8/34:53 pm
MIA
- ORD
1 stop8h 52m
United Airlines
Deal found 6/3![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1112:20 pm
MDW
- MIA
1 stop6h 40m
Southwest
Fri 8/147:15 am
MIA
- MDW
Nonstop3h 05m
Southwest
Deal found 6/4![Southwest logo]()
$331
This United Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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
Fri 8/145:01 pm
MIA
- ORD
1 stop7h 25m
United Airlines
Deal found 6/3![United Airlines logo]()
$345
This Southwest deal was found by Cheapflights users on 6/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:00 am
MDW
- MIA
Nonstop3h 10m
Southwest
Fri 8/217:15 am
MIA
- MDW
Nonstop3h 05m
Southwest
Deal found 6/2![Southwest logo]()
$335
This United Airlines deal was found by Cheapflights users on 5/31. 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 9/2110:32 am
ORD
- MIA
Nonstop3h 22m
United Airlines
Tue 9/291:20 pm
MIA
- ORD
1 stop6h 21m
United Airlines
Deal found 5/31![United Airlines logo]()
$353
This Southwest deal was found by Cheapflights users on 5/30. 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 6/1312:50 pm
MDW
- MIA
2 stops8h 15m
Southwest
Sat 6/207:15 am
MIA
- MDW
1 stop10h 50m
Southwest
Deal found 5/30![Southwest logo]()
$348
This United Airlines deal was found by Cheapflights users on 5/30. 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.
Thu 6/257:00 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Tue 6/304:12 pm
MIA
- ORD
Nonstop3h 45m
United Airlines
Deal found 5/30![United Airlines logo]()
$364
This United Airlines deal was found by Cheapflights users on 6/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:05 am
ORD
- MIA
1 stop6h 42m
United Airlines
Mon 9/145:01 pm
MIA
- ORD
1 stop7h 26m
United Airlines
Deal found 6/2![United Airlines logo]()
$378
This Southwest deal was found by Cheapflights users on 5/30. 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.
Thu 7/308:00 am
MDW
- MIA
Nonstop3h 00m
Southwest
Fri 7/315:25 am
MIA
- MDW
1 stop4h 50m
Southwest
Deal found 5/30![Southwest logo]()
$413
This Southwest deal was found by Cheapflights users on 5/30. 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 6/132:40 pm
MDW
- MIA
Nonstop3h 00m
Southwest
Thu 6/185:25 am
MIA
- MDW
1 stop4h 50m
Southwest
Deal found 5/30![Southwest logo]()
$427
This United Airlines deal was found by Cheapflights users on 5/31. 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.
Wed 6/1710:40 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Sun 6/215:39 pm
MIA
- ORD
Nonstop3h 43m
United Airlines
Deal found 5/31![United Airlines logo]()
$432
This Southwest deal was found by Cheapflights users on 6/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/188:00 am
MDW
- MIA
2 stops13h 30m
Southwest
Fri 7/245:25 am
MIA
- MDW
2 stops9h 00m
Southwest
Deal found 6/2![Southwest logo]()
$429
This United Airlines deal was found by Cheapflights users on 5/30. 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.
Thu 6/256:05 pm
ORD
- MIA
Nonstop3h 22m
United Airlines
Mon 6/294:12 pm
MIA
- ORD
Nonstop3h 45m
United Airlines
Deal found 5/30![United Airlines logo]()
$436
This Southwest deal was found by Cheapflights users on 5/31. 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 6/206:30 am
MDW
- MIA
2 stops8h 55m
Southwest
Sat 6/276:10 am
MIA
- MDW
2 stops6h 50m
Southwest
Deal found 5/31![Southwest logo]()
$432
This United Airlines deal was found by Cheapflights users on 5/30. 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.
Fri 6/267:00 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Mon 6/297:07 am
MIA
- ORD
1 stop7h 01m
United Airlines
Deal found 5/30![United Airlines logo]()
$446
Last-minute flights from Chicago to IslamoradaDiscover last-minute flight deals from Chicago to Islamorada. Data last updated June 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Islamorada. Data last updated June 4, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 5/30. 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.
Sat 6/131:29 pm
ORD
- MIA
1 stop6h 06m
Frontier
Sat 6/206:00 am
MIA
- ORD
1 stop19h 48m
Frontier
Deal found 5/30![Frontier logo]()
$286
This Cheapflightsfares deal was found by Cheapflights users on 5/30. 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.
Sat 6/139:48 pm
ORD
- MIA
1 stop31h 06m
Frontier
Tue 6/168:30 am
MIA
- ORD
1 stop12h 20m
Frontier
Deal found 5/30![Frontier logo]()
$287
This Super.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2412:04 pm
MDW
- MIA
1 stop9h 59m
Frontier
Tue 6/305:26 pm
MIA
- MDW
1 stop5h 45m
Frontier
Deal found 6/4![Frontier logo]()
$237
This Southwest deal was found by Cheapflights users on 6/1. 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.
Wed 6/2411:45 am
MDW
- MIA
Nonstop3h 00m
Southwest
Tue 6/304:00 pm
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 6/1![Southwest logo]()
$239
This Frontier deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/2711:59 am
MDW
- MIA
1 stop7h 36m
Frontier
Tue 7/75:28 pm
MIA
- MDW
1 stop5h 35m
Frontier
Deal found 6/3![Frontier logo]()
$243
This Priceline deal was found by Cheapflights users on 6/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/3012:27 pm
MDW
- MIA
1 stop9h 36m
Frontier
Tue 7/76:50 am
MIA
- MDW
1 stop11h 01m
Frontier
Deal found 6/2![Frontier logo]()
$230
This Super.com deal was found by Cheapflights users on 6/1. 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.
Wed 7/112:04 pm
MDW
- MIA
1 stop9h 59m
Frontier
Wed 7/85:28 pm
MIA
- MDW
1 stop5h 35m
Frontier
Deal found 6/1![Frontier logo]()
$228
This Frontier deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Wed 7/112:04 pm
MDW
- MIA
1 stop9h 59m
Frontier
Wed 7/156:50 am
MIA
- MDW
1 stop10h 00m
Frontier
Deal found 6/3![Frontier logo]()
$231
This Super.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Wed 7/156:05 am
MDW
- MIA
1 stop9h 28m
Frontier
Thu 8/205:26 pm
MIA
- MDW
1 stop5h 45m
Frontier
Deal found 6/3![Frontier logo]()
$233
This Frontier deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Wed 7/156:05 am
MDW
- MIA
1 stop6h 48m
Frontier
Sat 7/186:50 am
MIA
- MDW
1 stop11h 36m
Frontier
Deal found 6/3![Frontier logo]()
$244
This Expedia deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Wed 7/296:05 am
MDW
- MIA
1 stop9h 28m
Frontier
Sat 8/86:50 am
MIA
- MDW
1 stop11h 36m
Frontier
Deal found 6/3![Frontier logo]()
$235
This Expedia deal was found by Cheapflights users on 6/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:05 am
MDW
- MIA
1 stop9h 28m
Frontier
Tue 8/45:28 pm
MIA
- MDW
1 stop5h 35m
Frontier
Deal found 6/1![Frontier logo]()
$218
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 June 4, 2026.
Search for one-way flight options from Chicago to Islamorada. Find affordable one-way fares based on user searches. Data last updated June 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 8/121:50 pm
ORD
- MIA
1 stop23h 03m
Frontier
Deal found 6/3![Frontier logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 8/1211:06 am
MDW
- MIA
1 stop29h 41m
Frontier
Deal found 6/3![Frontier logo]()
$95
This Trip.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/306:00 am
MDW
- MIA
1 stop16h 03m
Frontier
Deal found 6/3![Frontier logo]()
$97
This Trip.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/246:55 am
ORD
- MIA
1 stop15h 08m
Frontier
Deal found 6/3![Frontier logo]()
$98
This Trip.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/246:00 am
MDW
- MIA
1 stop16h 03m
Frontier
Deal found 6/3![Frontier logo]()
$98
This Trip.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/61:50 pm
ORD
- MIA
1 stop8h 16m
Frontier
Deal found 6/4![Frontier logo]()
$110
This Trip.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 am
MDW
- MIA
1 stop9h 31m
Frontier
Deal found 6/3![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 10/12:03 pm
ORD
- MIA
1 stop6h 01m
Frontier
Deal found 6/3![Frontier logo]()
$111
This Cheapflightsfares deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:55 am
ORD
- MIA
1 stop5h 54m
Frontier
Deal found 6/4![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 6/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:00 am
MDW
- MIA
1 stop6h 29m
Frontier
Deal found 6/2![Frontier logo]()
$113
This SmartFares deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/711:30 am
ORD
- MIA
1 stop6h 48m
Delta
Deal found 6/3![Delta logo]()
$114
This Frontier deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Tue 10/139:20 am
ORD
- MIA
1 stop8h 02m
Frontier
Deal found 6/3![Frontier logo]()
$115
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 June 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $188 (Frontier) |
One-way from | $95 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $324 |
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 June 4, 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
MDW - MIA
MDWMIA
Chicago Midway
Wed 7/15
5:35 am-3:10 pm
1 stop8h 35m
Miami
Wed 7/22
4:00 pm-6:10 pm
Nonstop3h 10m
$249
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 7/22
6:05 pm-10:27 pm
Nonstop3h 22m
Miami
Tue 7/28
4:53 pm-12:45 am
1 stop8h 52m
$286
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Tue 9/1
7:30 am-3:55 pm
1 stop7h 25m
Miami
Sun 9/6
4:13 pm-6:46 pm
Nonstop3h 33m
$288
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 6/17
6:05 pm-10:27 pm
Nonstop3h 22m
Miami
Wed 6/24
4:06 pm-6:49 pm
Nonstop3h 43m
$307
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 7/8
3:00 pm-10:15 pm
2 stops6h 15m
Miami
Wed 7/22
11:25 am-7:05 pm
2 stops8h 40m
$308
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 7/8
3:00 pm-10:15 pm
2 stops6h 15m
Miami
Sat 7/11
7:15 am-5:05 pm
1 stop10h 50m
$309
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Fri 7/10
11:00 am-4:25 pm
1 stop4h 25m
Miami
Tue 7/14
4:00 pm-6:10 pm
Nonstop3h 10m
$327
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 8/11
12:20 pm-8:00 pm
1 stop6h 40m
Miami
Fri 8/14
7:15 am-9:20 am
Nonstop3h 05m
$331
Quickest round-trip
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Thu 8/13
8:00 am-12:10 pm
Nonstop3h 10m
Miami
Fri 8/21
7:15 am-9:20 am
Nonstop3h 05m
$335
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 7/29
6:05 pm-10:27 pm
Nonstop3h 22m
Miami
Mon 8/3
4:53 pm-12:45 am
1 stop8h 52m
$337
Showing 1-10 of 44 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 June 4, 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 afternoon.
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 June 4, 2026.
The most flights from CHI to I5L are scheduled on a Wednesday (50 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (15 on average).
How much does it cost to fly round-trip from Chicago to Islamorada?
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 May 30, 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 June 4, 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
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
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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Alternative routes for Chicago to Islamorada
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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 June 4, 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 June 4, 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 June 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$56 | Average$199 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$84 | Average$136 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$89 | Average$284 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$108 | Average$391 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$155 | Average$327 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$157 | Average$377 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$176 | Average$367 | FlexibilityNo cancel fee | On-time63% |