$45+ 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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Apr 17 — Apr 241
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 October, booked 41 days in advance, depart on a Monday or Sunday and return on a Thursday
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 March 18, 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 March 18, 2026.
This Super.com deal was found by Cheapflights users on 3/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/204:58 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Thu 4/239:21 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 3/13![Frontier logo]()
$99
This Frontier deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” 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.
Sun 4/193:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Thu 4/239:21 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 3/15![Frontier logo]()
$100
This Cheapflightsfares deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” 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.
Sun 4/124:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Sat 4/184:59 pm
MIA
- ORD
1 stop5h 13m
Spirit Airlines
Deal found 3/16![Spirit Airlines logo]()
$101
This CheapOair deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/134:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Sat 4/184:59 pm
MIA
- ORD
1 stop5h 13m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$102
This Super.com deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/23:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Sun 5/107:00 am
MIA
- ORD
Nonstop3h 37m
Frontier
Deal found 3/15![Frontier logo]()
$103
This Expedia deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” 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.
Sat 4/253:52 pm
ORD
- MIA
Nonstop3h 19m
Multiple Airlines
Sun 5/310:41 am
MIA
- ORD
Nonstop3h 24m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$104
This Cheapflightsfares deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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 4/84:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Mon 4/139:45 pm
MIA
- ORD
1 stop12h 05m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$105
This Priceline deal was found by Cheapflights users on 3/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/149:45 am
ORD
- MIA
1 stop9h 59m
Multiple Airlines
Thu 4/169:21 pm
MIA
- ORD
Nonstop3h 38m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$106
This Booking.com deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
- MIA
Nonstop3h 05m
Spirit Airlines
Mon 4/139:45 pm
MIA
- ORD
1 stop12h 05m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$107
This Trip.com deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” 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 4/116:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Wed 4/151:10 pm
MIA
- MDW
1 stop7h 21m
Frontier
Deal found 3/16![Frontier logo]()
$107
This CheapOair deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/114:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Sat 4/184:59 pm
MIA
- ORD
1 stop5h 13m
Spirit Airlines
Deal found 3/18![Spirit Airlines logo]()
$108
This Trip.com deal was found by Cheapflights users on 3/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:30 am
MDW
- MIA
Nonstop3h 10m
Multiple Airlines
Tue 4/143:12 pm
MIA
- MDW
1 stop8h 02m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$108
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 March 18, 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 March 18, 2026.
This Spirit deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/2610:55 am
ORD
- MIA
Nonstop3h 05m
Spirit Airlines
Sat 3/286:00 am
MIA
- ORD
Nonstop3h 25m
Spirit Airlines
Deal found 3/16![Spirit Airlines logo]()
$225
This Southwest deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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 4/257:50 am
MDW
- MIA
Nonstop3h 00m
Southwest
Thu 4/305:30 am
MIA
- MDW
1 stop5h 55m
Southwest
Deal found 3/17![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/247:10 am
ORD
- MIA
1 stop7h 27m
Delta
Wed 4/18:00 am
MIA
- ORD
1 stop6h 17m
Delta
Deal found 3/16![Delta logo]()
$381
This United Airlines deal was found by Cheapflights users on 3/13. 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 5/87:14 am
ORD
- MIA
Nonstop3h 23m
United Airlines
Sun 5/107:40 pm
MIA
- ORD
Nonstop3h 40m
United Airlines
Deal found 3/13![United Airlines logo]()
$413
This Southwest deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:50 pm
MDW
- MIA
Nonstop3h 00m
Southwest
Thu 5/76:20 am
MIA
- MDW
1 stop6h 40m
Southwest
Deal found 3/16![Southwest logo]()
$247
This KAYAK deal was found by Cheapflights users on 3/13. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/255:00 pm
ORD
- MIA
1 stop5h 43m
American Airlines
Thu 3/266:19 am
MIA
- ORD
Nonstop3h 34m
American Airlines
Deal found 3/13![American Airlines logo]()
$517
This Southwest deal was found by Cheapflights users on 3/13. 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.
Fri 5/86:50 pm
MDW
- MIA
Nonstop3h 00m
Southwest
Sun 5/106:10 am
MIA
- MDW
2 stops6h 50m
Southwest
Deal found 3/13![Southwest logo]()
$252
This Southwest deal was found by Cheapflights users on 3/13. 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.
Sun 5/176:45 pm
MDW
- MIA
Nonstop3h 00m
Southwest
Fri 5/226:05 am
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 3/13![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/23:45 pm
MDW
- MIA
Nonstop2h 55m
Southwest
Mon 5/46:40 am
MIA
- MDW
1 stop6h 25m
Southwest
Deal found 3/17![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” 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 4/65:25 am
MDW
- MIA
1 stop6h 55m
Southwest
Thu 4/166:40 am
MIA
- MDW
2 stops7h 30m
Southwest
Deal found 3/15![Southwest logo]()
$302
This United Airlines deal was found by Cheapflights users on 3/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/47:00 am
ORD
- MIA
Nonstop3h 22m
United Airlines
Sat 4/116:15 am
MIA
- ORD
1 stop9h 30m
United Airlines
Deal found 3/14![United Airlines logo]()
$461
This Southwest deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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 4/147:55 am
MDW
- MIA
Nonstop3h 00m
Southwest
Wed 4/1512:10 pm
MIA
- MDW
1 stop9h 10m
Southwest
Deal found 3/17![Southwest logo]()
$307
This United Airlines deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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 4/306:13 pm
ORD
- MIA
Nonstop3h 20m
United Airlines
Sun 5/34:20 pm
MIA
- ORD
Nonstop3h 40m
United Airlines
Deal found 3/17![United Airlines logo]()
$507
This Southwest deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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 5/14:35 pm
MDW
- MIA
1 stop4h 25m
Southwest
Mon 5/46:05 am
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 3/17![Southwest logo]()
$317
This United Airlines deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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 3/213:46 pm
ORD
- MIA
1 stop6h 20m
United Airlines
Mon 3/234:10 pm
MIA
- ORD
Nonstop3h 45m
United Airlines
Deal found 3/17![United Airlines logo]()
$520
This Southwest deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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 4/83:00 pm
MDW
- MIA
1 stop4h 40m
Southwest
Sat 4/118:25 am
MIA
- MDW
1 stop5h 45m
Southwest
Deal found 3/17![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/161:55 pm
ORD
- MIA
1 stop5h 25m
Southwest
Mon 5/185:30 am
MIA
- ORD
2 stops11h 00m
Southwest
Deal found 3/15![Southwest logo]()
$345
This Southwest deal was found by Cheapflights users on 3/14. 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.
Fri 4/172:40 pm
ORD
- MIA
2 stops6h 20m
Southwest
Mon 4/205:30 am
MIA
- ORD
2 stops11h 00m
Southwest
Deal found 3/14![Southwest logo]()
$362
This Southwest deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/205:55 am
ORD
- MIA
2 stops14h 15m
Southwest
Wed 5/2712:35 pm
MIA
- ORD
2 stops10h 20m
Southwest
Deal found 3/17![Southwest logo]()
$363
This Southwest deal was found by Cheapflights users on 3/14. 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 5/42:40 pm
ORD
- MIA
2 stops6h 20m
Southwest
Sun 5/106:10 am
MIA
- ORD
2 stops7h 40m
Southwest
Deal found 3/14![Southwest logo]()
$415
This Southwest deal was found by Cheapflights users on 3/14. 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.
Tue 3/242:40 pm
ORD
- MIA
1 stop6h 00m
Southwest
Thu 3/266:15 am
MIA
- ORD
2 stops7h 35m
Southwest
Deal found 3/14![Southwest logo]()
$484
Last-minute flights from Chicago to Key LargoDiscover last-minute flight deals from Chicago to Key Largo. Data last updated March 18, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Key Largo. Data last updated March 18, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 3/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:30 am
MDW
- MIA
Nonstop3h 10m
Multiple Airlines
Tue 4/143:12 pm
MIA
- MDW
1 stop8h 02m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$108
This Cheapflightsfares deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/44:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Mon 4/139:45 pm
MIA
- ORD
1 stop12h 05m
Spirit Airlines
Deal found 3/18![Spirit Airlines logo]()
$109
This Booking.com deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
- MIA
Nonstop3h 05m
Spirit Airlines
Mon 4/139:45 pm
MIA
- ORD
1 stop12h 05m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$107
This Cheapflightsfares deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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 4/84:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Mon 4/139:45 pm
MIA
- ORD
1 stop12h 05m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$105
This Trip.com deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” 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 4/116:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Wed 4/151:10 pm
MIA
- MDW
1 stop7h 21m
Frontier
Deal found 3/16![Frontier logo]()
$107
This CheapOair deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/114:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Sat 4/184:59 pm
MIA
- ORD
1 stop5h 13m
Spirit Airlines
Deal found 3/18![Spirit Airlines logo]()
$108
This Cheapflightsfares deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” 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.
Sun 4/124:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Sat 4/184:59 pm
MIA
- ORD
1 stop5h 13m
Spirit Airlines
Deal found 3/16![Spirit Airlines logo]()
$101
This CheapOair deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/134:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Sat 4/184:59 pm
MIA
- ORD
1 stop5h 13m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$102
This Priceline deal was found by Cheapflights users on 3/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/149:45 am
ORD
- MIA
1 stop9h 59m
Multiple Airlines
Thu 4/169:21 pm
MIA
- ORD
Nonstop3h 38m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$106
This Frontier deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” 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.
Sun 4/193:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Thu 4/239:21 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 3/15![Frontier logo]()
$100
This Super.com deal was found by Cheapflights users on 3/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/204:58 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Thu 4/239:21 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 3/13![Frontier logo]()
$99
This Expedia deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” 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.
Sat 4/253:52 pm
ORD
- MIA
Nonstop3h 19m
Multiple Airlines
Sun 5/310:41 am
MIA
- ORD
Nonstop3h 24m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$104
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 March 18, 2026.
Search for one-way flight options from Chicago to Key Largo. Find affordable one-way fares based on user searches. Data last updated March 18, 2026.
This Frontier deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/183:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Deal found 3/18![Frontier logo]()
$45
This Kiwi.com deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/44:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$46
This Kiwi.com deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” 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 4/1410:55 am
ORD
- MIA
Nonstop3h 05m
Spirit Airlines
Deal found 3/16![Spirit Airlines logo]()
$47
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/37:55 am
ORD
- MIA
Nonstop3h 19m
Frontier
Deal found 3/14![Frontier logo]()
$48
This Booking.com deal was found by Cheapflights users on 3/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/204:58 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Deal found 3/13![Frontier logo]()
$50
This Kiwi.com deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/309:42 pm
MDW
- MIA
Nonstop3h 08m
Frontier
Deal found 3/17![Frontier logo]()
$53
This Kiwi.com deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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.
Sun 4/54:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$53
This CheapOair deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/296:00 am
MDW
- MIA
Nonstop3h 13m
Frontier
Deal found 3/17![Frontier logo]()
$54
This Frontier deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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.
Sun 4/57:25 am
ORD
- MIA
Nonstop3h 19m
Frontier
Deal found 3/17![Frontier logo]()
$55
This Super.com deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/36:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Deal found 3/17![Frontier logo]()
$59
This Super.com deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/309:28 am
ORD
- MIA
Nonstop3h 15m
Frontier
Deal found 3/17![Frontier logo]()
$59
This Mytrip deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/118:10 am
ORD
- MIA
Nonstop3h 05m
Spirit Airlines
Deal found 3/16![Spirit Airlines logo]()
$61
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 March 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $99 (Super.com) |
One-way from | $45 (Frontier) |
Popular in | December |
Cheapest in | September |
Average price | $318 |
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 March 18, 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 3/26
10:55 am-3:00 pm
Nonstop3h 05m
Miami
Sat 3/28
6:00 am-8:25 am
Nonstop3h 25m
$225
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 4/25
7:50 am-11:50 am
Nonstop3h 00m
Miami
Thu 4/30
5:30 am-10:25 am
1 stop5h 55m
$247
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Thu 4/30
6:50 pm-10:50 pm
Nonstop3h 00m
Miami
Thu 5/7
6:20 am-12:00 pm
1 stop6h 40m
$247
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Fri 5/8
6:50 pm-10:50 pm
Nonstop3h 00m
Miami
Sun 5/10
6:10 am-12:00 pm
2 stops6h 50m
$252
Quickest round-trip
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sun 5/17
6:45 pm-10:45 pm
Nonstop3h 00m
Miami
Fri 5/22
6:05 am-8:20 am
Nonstop3h 15m
$272
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 5/2
3:45 pm-7:40 pm
Nonstop2h 55m
Miami
Mon 5/4
6:40 am-12:05 pm
1 stop6h 25m
$297
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Mon 4/6
5:25 am-1:20 pm
1 stop6h 55m
Miami
Thu 4/16
6:40 am-1:10 pm
2 stops7h 30m
$302
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 4/14
7:55 am-11:55 am
Nonstop3h 00m
Miami
Wed 4/15
12:10 pm-8:20 pm
1 stop9h 10m
$307
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Fri 5/1
4:35 pm-10:00 pm
1 stop4h 25m
Miami
Mon 5/4
6:05 am-8:20 am
Nonstop3h 15m
$317
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 4/8
3:00 pm-8:40 pm
1 stop4h 40m
Miami
Sat 4/11
8:25 am-1:10 pm
1 stop5h 45m
$327
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.
ORD-MIA
MDW-MIA
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Key Largo
CHI-KE9
ORD-MIA
MDW-MIA
How far ahead should I book a flight from Chicago to Key Largo?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Key Largo. Price data was last updated on March 13, 2026.
The best time to book flights from Chicago to Key Largo is 41 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Chicago to Key Largo?
Currently, October is the cheapest month in which you can book a flight from Chicago to Key Largo (average of $49). Flying from Chicago to Key Largo in July is currently the most expensive (average of $118). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to 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 March 18, 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 in the evening, which can drop the price by up to 14% versus a flight in the afternoon.
What is the cheapest day to fly from Chicago to 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 March 14, 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. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to 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 March 18, 2026.
The most flights from CHI to KE9 are scheduled on a Monday (59 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (49 on average).
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 March 18, 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
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
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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Alternative routes for Chicago to Key Largo
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Complete your trip
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Search flights from Chicago to Key Largo by cabin class
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Chicago and Key Largo flights
Browse other Chicago and Key Largo flight options. Last updated on March 18, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on March 18, 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 9 airlines flying from Chicago to Key Largo
Discover the top 9 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 March 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$56 | Average$182 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$70 | Average$226 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$84 | Average$146 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$89 | Average$234 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$108 | Average$376 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$377 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$156 | Average$356 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$176 | Average$249 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$176 | Average$361 | FlexibilityNo cancel fee | On-time63% |