$103+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Jul 25 — Aug 11
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 September or January, booked 76 days in advance, depart on a Monday or Saturday and return on a Friday
Cheap flight deals from Chicago to Key Largo
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Best
Last-minute
One-way
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 June 25, 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 June 25, 2026.
This deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:05 am
MDW
- MIA
1 stop6h 48m
Frontier
Tue 7/145:28 pm
MIA
- MDW
1 stop5h 35m
Frontier
Deal found 6/21![Frontier logo]()
$225
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/16:05 pm
ORD
- MIA
Nonstop3h 22m
United Airlines
Tue 8/48:48 am
MIA
- ORD
1 stop7h 05m
United Airlines
Deal found 6/22![United Airlines logo]()
$225
This Frontier deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 10/246:40 am
MDW
- MIA
1 stop10h 42m
Frontier
Tue 10/276:45 am
MIA
- MDW
1 stop5h 13m
Frontier
Deal found 6/21![Frontier logo]()
$226
This Frontier deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/611:06 am
MDW
- MIA
1 stop5h 41m
Frontier
Wed 8/1210:50 am
MIA
- MDW
1 stop12h 13m
Frontier
Deal found 6/21![Frontier logo]()
$227
This Southwest deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/205:30 am
MDW
- MIA
1 stop8h 10m
Southwest
Mon 8/247:00 am
MIA
- MDW
2 stops8h 10m
Southwest
Deal found 6/21![Southwest logo]()
$228
This Cheapflightsfares deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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.
Wed 7/159:57 pm
ORD
- MIA
1 stop30h 54m
Frontier
Tue 7/2110:15 pm
MIA
- ORD
1 stop32h 22m
Frontier
Deal found 6/21![Frontier logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/156:05 am
MDW
- MIA
1 stop6h 48m
Frontier
Wed 7/225:28 pm
MIA
- MDW
1 stop5h 35m
Frontier
Deal found 6/21![Frontier logo]()
$229
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 7/2911:45 am
MDW
- MIA
Nonstop3h 00m
Southwest
Sat 8/112:45 pm
MIA
- MDW
1 stop7h 40m
Southwest
Deal found 6/20![Southwest logo]()
$231
This United Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/146:00 am
ORD
- MIA
1 stop9h 16m
United Airlines
Wed 7/2212:30 pm
MIA
- ORD
Nonstop3h 43m
United Airlines
Deal found 6/21![United Airlines logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 9/511:45 am
MDW
- MIA
1 stop7h 44m
Frontier
Tue 9/85:28 pm
MIA
- MDW
1 stop6h 19m
Frontier
Deal found 6/25![Frontier logo]()
$232
This Cheapflightsfares deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/115:30 pm
ORD
- MIA
1 stop29h 51m
Frontier
Sat 8/1510:15 pm
MIA
- ORD
1 stop32h 22m
Frontier
Deal found 6/22![Frontier logo]()
$232
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/63:10 pm
MDW
- MIA
2 stops5h 55m
Southwest
Thu 8/134:50 pm
MIA
- MDW
2 stops6h 30m
Southwest
Deal found 6/22![Southwest logo]()
$233
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 June 25, 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 June 25, 2026.
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/277:30 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Sat 8/2911:30 am
MIA
- ORD
1 stop8h 00m
United Airlines
Deal found 6/23![United Airlines logo]()
$244
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1411:45 am
MDW
- MIA
Nonstop3h 00m
Southwest
Thu 7/232:50 pm
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 6/20![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:55 pm
ORD
- MIA
1 stop5h 57m
Delta
Sun 11/87:00 am
MIA
- ORD
1 stop6h 06m
Delta
Deal found 6/21![Delta logo]()
$344
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/256:05 pm
ORD
- MIA
Nonstop3h 22m
United Airlines
Mon 7/274:10 pm
MIA
- ORD
Nonstop3h 43m
United Airlines
Deal found 6/22![United Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/1112:50 pm
MDW
- MIA
2 stops8h 20m
Southwest
Tue 7/2111:45 am
MIA
- MDW
1 stop5h 10m
Southwest
Deal found 6/22![Southwest logo]()
$299
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/141:15 pm
ORD
- MIA
1 stop6h 39m
Delta
Sun 11/226:00 am
MIA
- ORD
1 stop5h 07m
Delta
Deal found 6/24![Delta logo]()
$344
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/145:00 am
MDW
- MIA
1 stop5h 25m
Southwest
Mon 8/177:15 am
MIA
- MDW
Nonstop3h 05m
Southwest
Deal found 6/22![Southwest logo]()
$313
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/157:00 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Sat 7/186:30 am
MIA
- ORD
1 stop9h 21m
United Airlines
Deal found 6/22![United Airlines logo]()
$321
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/71:05 pm
MDW
- MIA
1 stop6h 49m
Delta
Sun 12/136:00 am
MIA
- MDW
1 stop6h 56m
Delta
Deal found 6/23![Delta logo]()
$347
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/73:10 pm
MDW
- MIA
2 stops5h 55m
Southwest
Thu 8/136:25 pm
MIA
- MDW
1 stop4h 55m
Southwest
Deal found 6/23![Southwest logo]()
$328
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 10/155:55 pm
ORD
- MIA
1 stop5h 57m
Delta
Sun 10/188:00 am
MIA
- ORD
1 stop5h 37m
Delta
Deal found 6/24![Delta logo]()
$355
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/2210:33 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Mon 7/275:32 pm
MIA
- ORD
Nonstop3h 41m
United Airlines
Deal found 6/23![United Airlines logo]()
$367
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 7/2210:00 am
MDW
- MIA
1 stop5h 25m
Southwest
Sun 7/265:35 am
MIA
- MDW
2 stops6h 40m
Southwest
Deal found 6/24![Southwest logo]()
$336
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 12/115:55 pm
ORD
- MIA
1 stop5h 57m
Delta
Mon 12/147:30 pm
MIA
- ORD
1 stop5h 20m
Delta
Deal found 6/22![Delta logo]()
$366
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 11/127:20 am
MDW
- MIA
1 stop7h 35m
Southwest
Sun 11/156:50 am
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 6/23![Southwest logo]()
$337
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/2310:33 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Thu 7/308:48 am
MIA
- ORD
1 stop8h 51m
United Airlines
Deal found 6/22![United Airlines logo]()
$409
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 10/312:25 pm
MDW
- MIA
2 stops8h 45m
Southwest
Sun 10/115:25 am
MIA
- MDW
2 stops8h 50m
Southwest
Deal found 6/20![Southwest logo]()
$341
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/215:55 pm
ORD
- MIA
1 stop5h 57m
Delta
Thu 12/317:00 am
MIA
- ORD
1 stop5h 06m
Delta
Deal found 6/24![Delta logo]()
$403
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 11/298:30 pm
MDW
- MIA
Nonstop3h 00m
Southwest
Thu 12/312:35 pm
MIA
- MDW
Nonstop3h 20m
Southwest
Deal found 6/25![Southwest logo]()
$345
This United Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/237:30 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Fri 8/2812:17 pm
MIA
- ORD
Nonstop3h 31m
United Airlines
Deal found 6/20![United Airlines logo]()
$427
This Southwest deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/161:55 pm
MDW
- MIA
2 stops7h 55m
Southwest
Sat 8/227:00 am
MIA
- MDW
2 stops6h 30m
Southwest
Deal found 6/21![Southwest logo]()
$349
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/131:20 pm
MDW
- MIA
2 stops7h 45m
Southwest
Sun 8/165:50 am
MIA
- MDW
1 stop5h 05m
Southwest
Deal found 6/23![Southwest logo]()
$352
Last-minute flights from Chicago to Key LargoDiscover last-minute flight deals from Chicago to Key Largo. Data last updated June 25, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Key Largo. Data last updated June 25, 2026 and is based on user searches.
This deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:05 am
MDW
- MIA
1 stop6h 48m
Frontier
Tue 7/145:28 pm
MIA
- MDW
1 stop5h 35m
Frontier
Deal found 6/21![Frontier logo]()
$225
This United Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/146:00 am
ORD
- MIA
1 stop9h 16m
United Airlines
Wed 7/2212:30 pm
MIA
- ORD
Nonstop3h 43m
United Airlines
Deal found 6/21![United Airlines logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/149:33 pm
MIA
- ORD
1 stop26h 54m
Frontier
Deal found 6/23![Frontier logo]()
$235
This Cheapflightsfares deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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.
Wed 7/159:57 pm
ORD
- MIA
1 stop30h 54m
Frontier
Tue 7/2110:15 pm
MIA
- ORD
1 stop32h 22m
Frontier
Deal found 6/21![Frontier logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/156:05 am
MDW
- MIA
1 stop6h 48m
Frontier
Wed 7/225:28 pm
MIA
- MDW
1 stop5h 35m
Frontier
Deal found 6/21![Frontier logo]()
$229
This Frontier deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 7/1812:11 pm
MDW
- MIA
1 stop7h 18m
Frontier
Wed 7/225:28 pm
MIA
- MDW
1 stop5h 35m
Frontier
Deal found 6/24![Frontier logo]()
$236
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/2211:45 am
MDW
- MIA
Nonstop3h 00m
Southwest
Tue 7/2811:45 am
MIA
- MDW
1 stop5h 10m
Southwest
Deal found 6/22![Southwest logo]()
$227
This Frontier deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/251:50 pm
ORD
- MIA
1 stop5h 39m
Frontier
Tue 8/411:19 am
MIA
- ORD
1 stop9h 34m
Frontier
Deal found 6/25![Frontier logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/277:05 am
ORD
- MIA
1 stop5h 48m
Frontier
Tue 8/1110:50 am
MIA
- ORD
1 stop10h 03m
Frontier
Deal found 6/21![Frontier logo]()
$236
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 7/2911:45 am
MDW
- MIA
Nonstop3h 00m
Southwest
Sat 8/112:45 pm
MIA
- MDW
1 stop7h 40m
Southwest
Deal found 6/20![Southwest logo]()
$231
This Trip.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/296:05 am
MDW
- MIA
1 stop6h 48m
Frontier
Wed 8/56:50 am
MIA
- MDW
1 stop10h 00m
Frontier
Deal found 6/23![Frontier logo]()
$235
This Cheapflightsfares deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/307:05 am
ORD
- MIA
1 stop8h 28m
Frontier
Tue 8/49:33 pm
MIA
- ORD
1 stop26h 54m
Frontier
Deal found 6/25![Frontier logo]()
$237
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 June 25, 2026.
Search for one-way flight options from Chicago to Key Largo. Find affordable one-way fares based on user searches. Data last updated June 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/189:10 am
ORD
- MIA
1 stop28h 23m
Frontier
Deal found 6/21![Frontier logo]()
$103
This Frontier deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 8/196:05 am
MDW
- MIA
1 stop6h 27m
Frontier
Deal found 6/24![Frontier logo]()
$105
This Frontier deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 6/24![Frontier logo]()
$105
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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
Deal found 6/25![Southwest logo]()
$107
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/75:25 pm
MDW
- MIA
1 stop6h 27m
Delta
Deal found 6/23![Delta logo]()
$109
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:22 pm
ORD
- MIA
1 stop5h 33m
Delta
Deal found 6/23![Delta logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 10/57:25 am
MDW
- MIA
1 stop12h 39m
Frontier
Deal found 6/20![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 10/52:03 pm
ORD
- MIA
1 stop6h 01m
Frontier
Deal found 6/20![Frontier logo]()
$111
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/179:00 am
MDW
- MIA
1 stop6h 25m
Southwest
Deal found 6/23![Southwest logo]()
$112
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:40 am
ORD
- MIA
1 stop7h 14m
Delta
Deal found 6/23![Delta logo]()
$112
This Cheapflightsfares deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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.
Wed 7/151:50 pm
ORD
- MIA
1 stop8h 15m
Frontier
Deal found 6/23![Frontier logo]()
$113
This Frontier deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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
Deal found 6/24![Frontier logo]()
$115
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 June 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $225 (United Airlines) |
One-way from | $103 (Kiwi.com) |
Popular in | June |
Cheapest in | September |
Average price | $366 |
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 June 25, 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 - MIA
ORDMIA
Chicago O'Hare Intl
Thu 8/27
7:30 am-11:54 am
Nonstop3h 24m
Miami
Sat 8/29
11:30 am-6:30 pm
1 stop8h 00m
$244
Quickest round-trip
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 7/14
11:45 am-3:45 pm
Nonstop3h 00m
Miami
Thu 7/23
2:50 pm-5:00 pm
Nonstop3h 10m
$277
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Sat 7/25
6:05 pm-10:27 pm
Nonstop3h 22m
Miami
Mon 7/27
4:10 pm-6:53 pm
Nonstop3h 43m
$277
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 7/11
12:50 pm-10:10 pm
2 stops8h 20m
Miami
Tue 7/21
11:45 am-3:55 pm
1 stop5h 10m
$299
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Fri 8/14
5:00 am-11:25 am
1 stop5h 25m
Miami
Mon 8/17
7:15 am-9:20 am
Nonstop3h 05m
$313
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 7/15
7:00 am-11:24 am
Nonstop3h 24m
Miami
Sat 7/18
6:30 am-2:51 pm
1 stop9h 21m
$321
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Fri 8/7
3:10 pm-10:05 pm
2 stops5h 55m
Miami
Thu 8/13
6:25 pm-10:20 pm
1 stop4h 55m
$328
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 7/22
10:00 am-4:25 pm
1 stop5h 25m
Miami
Sun 7/26
5:35 am-11:15 am
2 stops6h 40m
$336
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Thu 11/12
7:20 am-3:55 pm
1 stop7h 35m
Miami
Sun 11/15
6:50 am-9:00 am
Nonstop3h 10m
$337
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 10/3
12:25 pm-10:10 pm
2 stops8h 45m
Miami
Sun 10/11
5:25 am-1:15 pm
2 stops8h 50m
$341
Showing 1-10 of 43 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 June 25, 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 12% versus a flight in the afternoon.
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 June 25, 2026.
The most flights from CHI to KE9 are scheduled on a Thursday (55 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (34 on average).
How much does it cost to fly round-trip from Chicago to Key Largo?
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 June 20, 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 June 25, 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.
Crew
8.6
Overall
7.9
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Overall
7.9
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Overall
7.9
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Overall
7.9
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Overall
7.9
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Overall
7.9
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
Find useful and relevant information for your journey from Chicago to 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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Complete your trip
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Chicago and Key Largo flights
Browse other Chicago and Key Largo flight options. Last updated on June 25, 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 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Key Largo flights
Consider these flights traveling from Chicago to Key Largo.
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 June 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$56 | Average$202 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$84 | Average$134 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$89 | Average$258 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$108 | Average$378 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$157 | Average$378 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$367 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$176 | Average$370 | FlexibilityNo cancel fee | On-time63% |