$64+ 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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Jun 7 — Jun 141
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 76 days in advance, depart on a Monday or Sunday 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 May 8, 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 May 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/96:55 am
ORD
- MIA
1 stop8h 36m
Frontier
Tue 6/1611:19 am
MIA
- ORD
1 stop9h 31m
Frontier
Deal found 5/6![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/47:05 am
ORD
- MIA
1 stop5h 48m
Frontier
Tue 8/1111:19 am
MIA
- ORD
1 stop9h 34m
Frontier
Deal found 5/5![Frontier logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/101:29 pm
ORD
- MIA
1 stop8h 34m
Frontier
Tue 6/168:30 am
MIA
- ORD
1 stop12h 20m
Frontier
Deal found 5/6![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/106:00 am
MDW
- MIA
1 stop6h 49m
Frontier
Tue 6/1611:19 am
MIA
- MDW
1 stop11h 52m
Frontier
Deal found 5/6![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/21:29 pm
ORD
- MIA
1 stop8h 18m
Frontier
Tue 6/911:19 am
MIA
- ORD
1 stop9h 34m
Frontier
Deal found 5/5![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/212:27 pm
MDW
- MIA
1 stop9h 20m
Frontier
Tue 6/96:00 am
MIA
- MDW
1 stop6h 12m
Frontier
Deal found 5/5![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/261:50 pm
ORD
- MIA
1 stop7h 57m
Frontier
Thu 5/2811:23 am
MIA
- ORD
1 stop9h 18m
Frontier
Deal found 5/4![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
MDW
- MIA
1 stop6h 20m
Frontier
Mon 6/18:10 am
MIA
- MDW
1 stop28h 02m
Frontier
Deal found 5/4![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:50 pm
ORD
- MIA
1 stop7h 57m
Frontier
Tue 6/211:23 am
MIA
- ORD
1 stop9h 06m
Frontier
Deal found 5/4![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
MDW
- MIA
1 stop6h 20m
Frontier
Wed 6/105:26 pm
MIA
- MDW
1 stop5h 45m
Frontier
Deal found 5/4![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:55 am
ORD
- MIA
1 stop8h 32m
Frontier
Mon 6/18:10 am
MIA
- ORD
1 stop24h 45m
Frontier
Deal found 5/4![Frontier logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/261:50 pm
ORD
- MIA
1 stop7h 57m
Frontier
Tue 6/211:23 am
MIA
- ORD
1 stop9h 06m
Frontier
Deal found 5/4![Frontier logo]()
$145
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 May 8, 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 May 8, 2026.
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/210:15 am
MDW
- MIA
1 stop5h 35m
Southwest
Wed 6/36:40 am
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 5/7![Southwest logo]()
$209
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/243:22 pm
ORD
- MIA
1 stop5h 55m
Delta
Tue 7/72:09 pm
MIA
- ORD
1 stop7h 24m
Delta
Deal found 5/7![Delta logo]()
$229
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/184:12 pm
MIA
- ORD
Nonstop3h 45m
United Airlines
Deal found 5/5![United Airlines logo]()
$258
This KAYAK deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 7/85:59 pm
ORD
- MIA
Nonstop3h 21m
American Airlines
Sun 7/129:50 pm
MIA
- ORD
Nonstop3h 36m
American Airlines
Deal found 5/7![American Airlines logo]()
$380
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/17:50 am
MDW
- MIA
1 stop4h 20m
Southwest
Wed 6/36:40 am
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 5/6![Southwest logo]()
$216
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:45 am
MDW
- MIA
1 stop6h 00m
Southwest
Wed 6/104:00 pm
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 5/4![Southwest logo]()
$220
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1011:50 am
MDW
- MIA
2 stops8h 30m
Southwest
Tue 6/161:45 pm
MIA
- MDW
2 stops7h 05m
Southwest
Deal found 5/6![Southwest logo]()
$229
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:10 pm
MDW
- MIA
1 stop6h 33m
Delta
Tue 5/266:00 am
MIA
- MDW
1 stop5h 00m
Delta
Deal found 5/3![Delta logo]()
$307
This United Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:00 am
ORD
- MIA
1 stop7h 52m
United Airlines
Wed 7/85:40 pm
MIA
- ORD
Nonstop3h 41m
United Airlines
Deal found 5/2![United Airlines logo]()
$323
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/256:00 am
MDW
- MIA
1 stop6h 04m
Delta
Tue 6/301:38 pm
MIA
- MDW
1 stop5h 53m
Delta
Deal found 5/5![Delta logo]()
$311
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/246:00 pm
MDW
- MIA
Nonstop2h 55m
Southwest
Wed 5/276:40 am
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 5/5![Southwest logo]()
$258
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:05 pm
ORD
- MIA
Nonstop3h 22m
United Airlines
Sun 5/315:39 pm
MIA
- ORD
Nonstop3h 44m
United Airlines
Deal found 5/4![United Airlines logo]()
$355
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/247:00 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Sat 8/17:07 am
MIA
- ORD
1 stop8h 46m
United Airlines
Deal found 5/5![United Airlines logo]()
$370
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/252:40 pm
ORD
- MIA
2 stops6h 20m
Southwest
Thu 5/286:20 am
MIA
- ORD
2 stops7h 30m
Southwest
Deal found 5/4![Southwest logo]()
$339
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:05 pm
ORD
- MIA
Nonstop3h 22m
United Airlines
Mon 8/35:40 pm
MIA
- ORD
Nonstop3h 41m
United Airlines
Deal found 5/5![United Airlines logo]()
$381
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/2710:30 am
ORD
- MIA
1 stop9h 03m
United Airlines
Wed 7/14:12 pm
MIA
- ORD
Nonstop3h 45m
United Airlines
Deal found 5/7![United Airlines logo]()
$387
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 5/2710:15 am
MDW
- MIA
1 stop5h 35m
Southwest
Sun 5/316:45 am
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 5/6![Southwest logo]()
$354
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/296:50 pm
MDW
- MIA
Nonstop3h 00m
Southwest
Mon 6/16:05 am
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 5/5![Southwest logo]()
$355
This United Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:00 am
ORD
- MIA
1 stop8h 38m
United Airlines
Mon 6/15:39 pm
MIA
- ORD
Nonstop3h 43m
United Airlines
Deal found 5/3![United Airlines logo]()
$410
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1610:00 am
MDW
- MIA
1 stop4h 25m
Southwest
Mon 5/186:20 am
MIA
- MDW
2 stops6h 30m
Southwest
Deal found 5/2![Southwest logo]()
$362
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:00 am
ORD
- MIA
1 stop7h 38m
United Airlines
Wed 8/55:40 pm
MIA
- ORD
Nonstop3h 41m
United Airlines
Deal found 5/4![United Airlines logo]()
$413
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:45 pm
MDW
- MIA
Nonstop3h 00m
Southwest
Tue 5/196:15 am
MIA
- MDW
1 stop6h 25m
Southwest
Deal found 5/3![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2711:55 am
ORD
- MIA
2 stops9h 00m
Southwest
Sun 5/316:10 am
MIA
- ORD
2 stops7h 40m
Southwest
Deal found 5/4![Southwest logo]()
$424
Last-minute flights from Chicago to Key LargoDiscover last-minute flight deals from Chicago to Key Largo. Data last updated May 8, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Key Largo. Data last updated May 8, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/261:50 pm
ORD
- MIA
1 stop7h 57m
Frontier
Thu 5/2811:23 am
MIA
- ORD
1 stop9h 18m
Frontier
Deal found 5/4![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/261:50 pm
ORD
- MIA
1 stop7h 57m
Frontier
Tue 6/211:23 am
MIA
- ORD
1 stop9h 06m
Frontier
Deal found 5/4![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
MDW
- MIA
1 stop6h 20m
Frontier
Mon 6/18:10 am
MIA
- MDW
1 stop28h 02m
Frontier
Deal found 5/4![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:50 pm
ORD
- MIA
1 stop7h 57m
Frontier
Tue 6/211:23 am
MIA
- ORD
1 stop9h 06m
Frontier
Deal found 5/4![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
MDW
- MIA
1 stop6h 20m
Frontier
Wed 6/311:23 am
MIA
- MDW
1 stop11h 39m
Frontier
Deal found 5/3![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:55 am
ORD
- MIA
1 stop8h 32m
Frontier
Mon 6/18:10 am
MIA
- ORD
1 stop24h 45m
Frontier
Deal found 5/4![Frontier logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/212:27 pm
MDW
- MIA
1 stop9h 20m
Frontier
Tue 6/96:00 am
MIA
- MDW
1 stop6h 12m
Frontier
Deal found 5/5![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/21:29 pm
ORD
- MIA
1 stop8h 18m
Frontier
Tue 6/911:19 am
MIA
- ORD
1 stop9h 34m
Frontier
Deal found 5/5![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
MDW
- MIA
1 stop6h 20m
Frontier
Wed 6/105:26 pm
MIA
- MDW
1 stop5h 45m
Frontier
Deal found 5/4![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/96:55 am
ORD
- MIA
1 stop8h 36m
Frontier
Tue 6/1611:19 am
MIA
- ORD
1 stop9h 31m
Frontier
Deal found 5/6![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/106:00 am
MDW
- MIA
1 stop6h 49m
Frontier
Tue 6/1611:19 am
MIA
- MDW
1 stop11h 52m
Frontier
Deal found 5/6![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/101:29 pm
ORD
- MIA
1 stop8h 34m
Frontier
Tue 6/168:30 am
MIA
- ORD
1 stop12h 20m
Frontier
Deal found 5/6![Frontier logo]()
$132
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 May 8, 2026.
Search for one-way flight options from Chicago to Key Largo. Find affordable one-way fares based on user searches. Data last updated May 8, 2026.
This Trip.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:55 am
ORD
- MIA
1 stop14h 52m
Frontier
Deal found 5/7![Frontier logo]()
$64
This Trip.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:00 am
MDW
- MIA
1 stop9h 31m
Frontier
Deal found 5/6![Frontier logo]()
$64
This Trip.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/31:29 pm
ORD
- MIA
1 stop8h 18m
Frontier
Deal found 5/5![Frontier logo]()
$65
This Trip.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:04 pm
MDW
- MIA
1 stop9h 43m
Frontier
Deal found 5/5![Frontier logo]()
$65
This Trip.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:50 pm
ORD
- MIA
1 stop7h 57m
Frontier
Deal found 5/4![Frontier logo]()
$69
This Trip.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
MDW
- MIA
1 stop9h 27m
Frontier
Deal found 5/4![Frontier logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/161:29 pm
ORD
- MIA
1 stop8h 34m
Frontier
Deal found 5/5![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/16:00 am
MDW
- MIA
1 stop16h 03m
Frontier
Deal found 5/5![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/212:27 pm
MDW
- MIA
1 stop9h 20m
Frontier
Deal found 5/3![Frontier logo]()
$71
This WAYA deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:55 am
ORD
- MIA
1 stop8h 32m
Frontier
Deal found 5/4![Frontier logo]()
$74
This WAYA deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:00 am
MDW
- MIA
1 stop9h 27m
Frontier
Deal found 5/4![Frontier logo]()
$74
This Trip.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:00 am
MDW
- MIA
1 stop9h 27m
Frontier
Deal found 5/5![Frontier logo]()
$77
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 May 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $129 (Kiwi.com) |
One-way from | $64 (Trip.com) |
Popular in | December |
Cheapest in | September |
Average price | $284 |
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 May 8, 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
MDW - MIA
MDWMIA
Chicago Midway
Tue 6/2
10:15 am-4:50 pm
1 stop5h 35m
Miami
Wed 6/3
6:40 am-8:50 am
Nonstop3h 10m
$209
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Mon 6/1
7:50 am-1:10 pm
1 stop4h 20m
Miami
Wed 6/3
6:40 am-8:50 am
Nonstop3h 10m
$216
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 5/30
7:45 am-2:45 pm
1 stop6h 00m
Miami
Wed 6/10
4:00 pm-6:10 pm
Nonstop3h 10m
$220
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 6/24
3:22 pm-10:17 pm
1 stop5h 55m
Miami
Tue 7/7
2:09 pm-8:33 pm
1 stop7h 24m
$229
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 6/10
11:50 am-9:20 pm
2 stops8h 30m
Miami
Tue 6/16
1:45 pm-7:50 pm
2 stops7h 05m
$229
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 7/15
7:00 am-11:24 am
Nonstop3h 24m
Miami
Sat 7/18
4:12 pm-6:57 pm
Nonstop3h 45m
$258
Quickest round-trip
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sun 5/24
6:00 pm-9:55 pm
Nonstop2h 55m
Miami
Wed 5/27
6:40 am-8:50 am
Nonstop3h 10m
$258
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 5/23
5:10 pm-12:43 am
1 stop6h 33m
Miami
Tue 5/26
6:00 am-10:00 am
1 stop5h 00m
$307
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Thu 6/25
6:00 am-1:04 pm
1 stop6h 04m
Miami
Tue 6/30
1:38 pm-6:31 pm
1 stop5h 53m
$311
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Sat 7/4
6:00 am-2:52 pm
1 stop7h 52m
Miami
Wed 7/8
5:40 pm-8:21 pm
Nonstop3h 41m
$323
Showing 1-10 of 47 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
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 May 8, 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 13% 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 May 2, 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 May 8, 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 (27 on average).
How much does it cost to fly round-trip from Chicago to Key Largo?
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 May 8, 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.
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Food
7.0
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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Alternative routes for Chicago to Key Largo
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Complete your trip
Complete your trip to Key Largo by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Key Largo by cabin class
Find flights from Chicago to Key Largo, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Key Largo flights
Browse other Chicago and Key Largo flight options. Last updated on May 8, 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 May 8, 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 May 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$56 | Average$185 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$68 | Average$232 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$84 | Average$138 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$89 | Average$272 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$108 | Average$385 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$155 | Average$367 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$156 | Average$370 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$176 | Average$249 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$176 | Average$367 | FlexibilityNo cancel fee | On-time63% |