$87+ Cheap flights from Chicago (CHI) to Key Largo, 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Sep 14 — Sep 211
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Key Largo 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 Key Largo are usually found in January or September, booked 65 days in advance, depart on a Monday or Saturday and return on a Thursday
Cheap flight deals from Chicago to Key Largo
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Cheapest flights from Chicago to Key LargoExplore the most affordable flight options available from Chicago to Key Largo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 15, 2026.
Explore the most affordable flight options available from Chicago to Key Largo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/1110:26 am -
1 stop9h 07m
Tue 9/155:32 am -
1 stop7h 19m
Deal found 8/10![Frontier logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/157:25 am -
1 stop9h 34m
Tue 9/225:32 am -
1 stop7h 19m
Deal found 8/10![Frontier logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/86:05 am -
1 stop6h 27m
Tue 9/155:32 am -
1 stop13h 14m
Deal found 8/11![Frontier logo]()
$174
This Cheapflightsfares deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/68:00 am -
1 stop13h 21m
Mon 11/97:00 am -
1 stop13h 55m
Deal found 8/14![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/121:06 pm -
1 stop7h 54m
Tue 9/155:32 am -
1 stop13h 14m
Deal found 8/11![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 9/167:28 pm -
1 stop14h 02m
Sun 9/208:50 pm -
1 stop17h 40m
Deal found 8/13![Frontier logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 8/316:05 am -
1 stop6h 27m
Wed 9/25:28 pm -
1 stop6h 19m
Deal found 8/11![Frontier logo]()
$176
This Cheapflightsfares deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 10/3111:06 am -
1 stop17h 42m
Fri 11/68:00 am -
1 stop14h 34m
Deal found 8/11![Frontier logo]()
$177
This Frontier deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1112:54 pm -
1 stop8h 06m
Mon 9/215:34 pm -
1 stop7h 10m
Deal found 8/14![Frontier logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:20 am -
1 stop6h 22m
Mon 9/145:32 am -
1 stop13h 51m
Deal found 8/13![Frontier logo]()
$178
This Super.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/26:05 am -
1 stop6h 27m
Tue 9/85:28 pm -
1 stop6h 19m
Deal found 8/11![Frontier logo]()
$178
This Frontier deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:01 pm -
1 stop7h 59m
Wed 10/75:32 am -
1 stop7h 19m
Deal found 8/10![Frontier logo]()
$179
Best flights from Chicago to Key LargoDiscover carefully curated flight deals from Chicago to Key Largo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 15, 2026.
Discover carefully curated flight deals from Chicago to Key Largo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 15, 2026.
This United Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 10/97:30 am -
Nonstop3h 25m
Tue 10/134:01 pm -
Nonstop3h 31m
Deal found 8/13![United Airlines logo]()
$226
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 -
2 stops7h 35m
Sat 10/36:45 am -
2 stops9h 05m
Deal found 8/12![Southwest logo]()
$255
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:27 pm -
1 stop6h 45m
Mon 10/191:19 pm -
1 stop5h 41m
Deal found 8/12![Delta logo]()
$393
This United Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:30 am -
Nonstop3h 25m
Sat 10/37:00 am -
1 stop6h 54m
Deal found 8/12![United Airlines logo]()
$235
This United Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 9/97:30 am -
1 stop7h 25m
Wed 9/163:57 pm -
Nonstop3h 33m
Deal found 8/13![United Airlines logo]()
$235
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/129:55 am -
2 stops8h 25m
Sat 9/197:00 am -
2 stops6h 30m
Deal found 8/14![Southwest logo]()
$284
This United Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/87:30 am -
Nonstop3h 24m
Thu 9/105:37 pm -
1 stop7h 51m
Deal found 8/12![United Airlines logo]()
$246
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 -
1 stop4h 30m
Fri 9/187:15 am -
Nonstop3h 05m
Deal found 8/12![Southwest logo]()
$291
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 10/97:30 am -
Nonstop3h 25m
Sat 10/178:54 am -
1 stop8h 40m
Deal found 8/11![United Airlines logo]()
$290
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/239:25 am -
Nonstop3h 00m
Fri 10/26:40 am -
Nonstop3h 05m
Deal found 8/11![Southwest logo]()
$324
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:25 am -
Nonstop3h 25m
Wed 10/712:29 pm -
Nonstop3h 31m
Deal found 8/10![United Airlines logo]()
$315
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/241:20 pm -
2 stops7h 50m
Thu 10/16:10 pm -
2 stops6h 45m
Deal found 8/10![Southwest logo]()
$351
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:30 am -
Nonstop3h 24m
Mon 9/213:57 pm -
Nonstop3h 33m
Deal found 8/11![United Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/68:55 am -
1 stop10h 10m
Tue 9/811:50 am -
2 stops8h 15m
Deal found 8/10![Southwest logo]()
$363
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/610:48 am -
Nonstop3h 22m
Tue 9/85:01 pm -
1 stop8h 58m
Deal found 8/10![United Airlines logo]()
$342
This Southwest deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 9/38:00 am -
Nonstop3h 10m
Sat 9/57:00 am -
1 stop6h 35m
Deal found 8/13![Southwest logo]()
$395
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 8/287:25 am -
1 stop6h 55m
Tue 9/14:00 pm -
Nonstop3h 05m
Deal found 8/11![Southwest logo]()
$404
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/148:40 am -
1 stop9h 12m
Tue 9/153:57 pm -
Nonstop3h 33m
Deal found 8/10![United Airlines logo]()
$385
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 10/232:45 pm -
2 stops7h 10m
Sun 10/256:20 am -
2 stops8h 35m
Deal found 8/11![Southwest logo]()
$414
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/167:30 am -
Nonstop3h 24m
Fri 9/2512:29 pm -
Nonstop3h 31m
Deal found 8/10![United Airlines logo]()
$409
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/48:00 am -
Nonstop3h 10m
Sun 9/67:40 am -
1 stop5h 00m
Deal found 8/10![Southwest logo]()
$415
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 10/275:00 am -
1 stop6h 09m
Sun 11/17:00 am -
Nonstop3h 31m
Deal found 8/10![United Airlines logo]()
$427
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 10/218:50 am -
2 stops9h 02m
Thu 10/227:00 am -
1 stop6h 54m
Deal found 8/11![United Airlines logo]()
$450
Last-minute flights from Chicago to Key LargoDiscover last-minute flight deals from Chicago to Key Largo. Data last updated August 15, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Key Largo. Data last updated August 15, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 8/316:05 am -
1 stop6h 27m
Wed 9/25:28 pm -
1 stop6h 19m
Deal found 8/11![Frontier logo]()
$176
This Frontier deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/16:05 am -
1 stop6h 27m
Sat 9/55:28 pm -
1 stop6h 19m
Deal found 8/10![Frontier logo]()
$179
This Super.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/26:05 am -
1 stop6h 27m
Tue 9/85:28 pm -
1 stop6h 19m
Deal found 8/11![Frontier logo]()
$178
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/68:55 am -
1 stop10h 10m
Fri 9/114:00 pm -
1 stop7h 55m
Deal found 8/11![Southwest logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/86:05 am -
1 stop6h 27m
Tue 9/155:32 am -
1 stop13h 14m
Deal found 8/11![Frontier logo]()
$174
This Southwest deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 9/89:25 am -
Nonstop3h 00m
Fri 9/117:15 am -
Nonstop3h 05m
Deal found 8/13![Southwest logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/811:50 am -
1 stop10h 15m
Fri 9/119:30 pm -
1 stop21h 21m
Deal found 8/11![Frontier logo]()
$185
This Frontier deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1112:54 pm -
1 stop8h 06m
Mon 9/215:34 pm -
1 stop7h 10m
Deal found 8/14![Frontier logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/121:06 pm -
1 stop7h 54m
Tue 9/155:32 am -
1 stop13h 14m
Deal found 8/11![Frontier logo]()
$175
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1211:45 am -
2 stops7h 35m
Tue 9/154:00 pm -
Nonstop3h 05m
Deal found 8/14![Southwest logo]()
$186
This Frontier deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 9/191:06 pm -
1 stop7h 54m
Mon 9/215:34 pm -
1 stop7h 10m
Deal found 8/13![Frontier logo]()
$180
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/288:00 am -
Nonstop3h 10m
Mon 10/54:10 pm -
1 stop9h 05m
Deal found 8/14![Southwest logo]()
$181
One-way flights from Chicago to Key LargoSearch for one-way flight options from Chicago to Key Largo. Find affordable one-way fares based on user searches. Data last updated August 15, 2026.
Search for one-way flight options from Chicago to Key Largo. Find affordable one-way fares based on user searches. Data last updated August 15, 2026.
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/511:45 am -
2 stops7h 35m
Deal found 8/11![Southwest logo]()
$87
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 11/102:03 pm -
1 stop18h 20m
Deal found 8/10![Frontier logo]()
$87
This Super.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 10/56:25 am -
1 stop9h 04m
Deal found 8/12![Frontier logo]()
$89
This Trip.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1010:26 am -
1 stop9h 07m
Deal found 8/10![Frontier logo]()
$89
This Frontier deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 9/216:25 am -
1 stop9h 04m
Deal found 8/13![Frontier logo]()
$90
This Frontier deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 9/147:25 am -
1 stop11h 20m
Deal found 8/13![Frontier logo]()
$90
This Priceline deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/141:12 pm -
1 stop7h 47m
Deal found 8/14![Frontier logo]()
$91
This Super.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/252:46 pm -
1 stop22h 53m
Deal found 8/14![Frontier logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/86:05 am -
1 stop9h 16m
Deal found 8/10![Frontier logo]()
$92
This Cheapflightsfares deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:25 am -
1 stop11h 20m
Deal found 8/14![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/96:25 am -
1 stop13h 13m
Deal found 8/12![Frontier logo]()
$93
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1411:35 am -
Nonstop3h 10m
Deal found 8/14![Southwest logo]()
$96
Find flight deals from Chicago to Key Largo
Keep the following information in mind while searching for Chicago to Key Largo flight deals. Data was last updated August 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $173 (Kiwi.com) |
One-way from | $87 (Southwest) |
Popular in | July |
Cheapest in | January |
Average price | $303 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Key Largo 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 15, 2026.
Use the filters below to find and compare flights from Chicago to Key Largo that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMiami
ORD Chicago O'Hare Intl - MIA Miami
ORDMIA
Chicago O'Hare Intl
Fri 10/9
7:30 am-11:55 am
Nonstop3h 25m
Miami
Tue 10/13
4:01 pm-6:32 pm
Nonstop3h 31m
$226
ChicagoMiami
ORD Chicago O'Hare Intl - MIA Miami
ORDMIA
Chicago O'Hare Intl
Tue 9/29
7:30 am-11:55 am
Nonstop3h 25m
Miami
Sat 10/3
7:00 am-12:54 pm
1 stop6h 54m
$235
ChicagoMiami
ORD Chicago O'Hare Intl - MIA Miami
ORDMIA
Chicago O'Hare Intl
Wed 9/9
7:30 am-3:55 pm
1 stop7h 25m
Miami
Wed 9/16
3:57 pm-6:30 pm
Nonstop3h 33m
$235
ChicagoMiami
ORD Chicago O'Hare Intl - MIA Miami
ORDMIA
Chicago O'Hare Intl
Tue 9/8
7:30 am-11:54 am
Nonstop3h 24m
Miami
Thu 9/10
5:37 pm-12:28 am
1 stop7h 51m
$246
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Sat 9/26
11:45 am-8:20 pm
2 stops7h 35m
Miami
Sat 10/3
6:45 am-2:50 pm
2 stops9h 05m
$255
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Sat 9/12
9:55 am-7:20 pm
2 stops8h 25m
Miami
Sat 9/19
7:00 am-12:30 pm
2 stops6h 30m
$284
ChicagoMiami
ORD Chicago O'Hare Intl - MIA Miami
ORDMIA
Chicago O'Hare Intl
Fri 10/9
7:30 am-11:55 am
Nonstop3h 25m
Miami
Sat 10/17
8:54 am-4:34 pm
1 stop8h 40m
$290
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Fri 9/11
3:20 pm-8:50 pm
1 stop4h 30m
Miami
Fri 9/18
7:15 am-9:20 am
Nonstop3h 05m
$291
ChicagoMiami
ORD Chicago O'Hare Intl - MIA Miami
ORDMIA
Chicago O'Hare Intl
Sat 9/26
7:25 am-11:50 am
Nonstop3h 25m
Miami
Wed 10/7
12:29 pm-3:00 pm
Nonstop3h 31m
$315
Quickest round-trip
ChicagoMiami
MDW Chicago Midway - MIA Miami
MDWMIA
Chicago Midway
Wed 9/23
9:25 am-1:25 pm
Nonstop3h 00m
Miami
Fri 10/2
6:40 am-8:45 am
Nonstop3h 05m
$324
Showing 1-10 of 46 resultsSorted by cheapest first
Best time to book a flight from Chicago to Key Largo
Have a flexible travel schedule? Discover the best time to fly to Key Largo 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 Key Largo
CHI-KE9
MDW-MIA
ORD-MIA
What is the cheapest time of day to fly from CHI to KE9?
Find hourly flight availability from Chicago to Key Largo. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 15, 2026.
When flying from Chicago to Key Largo, 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 Key Largo
Explore weekly flight availability from Chicago to Key Largo. 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 15, 2026.
The most flights from CHI to KE9 are scheduled on a Wednesday (49 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (41 on average).
How much does it cost to fly round-trip from Chicago to Key Largo?
Airfare is below average for this route at the moment.
Chicago to Key Largo flights typically cost between $222 and $381 in September.The cheapest round-trip price found within the last 5 days was $173 on Frontier (Sep 11-Sep 15).
What is the cheapest day to fly from Chicago to Key Largo?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Key Largo. Price data was last updated on August 8, 2026.
Travelers seeking maximum savings on their Chicago to Key Largo 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 Key Largo
Get insights into the airlines that provide service to Key Largo. 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 Key Largo. Reviews last updated August 15, 2026.
Read through reviews of airlines operating flights from Chicago to Key Largo, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
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 Key Largo. 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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Chicago and Key Largo flights
Browse other Chicago and Key Largo flight options. Last updated on August 15, 2026.
Other flights from Chicago
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Popular flight searches
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Chicago to Key Largo flights
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Top 7 airlines flying from Chicago to Key Largo
Discover the top 7 airlines that operate flights from Chicago to Key Largo. 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 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$56 | Average$210 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$84 | Average$130 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$89 | Average$257 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$108 | Average$373 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$157 | Average$378 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$161 | Average$365 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$166 | Average$387 | FlexibilityNo cancel fee | On-time63% |