$55+ Cheap flights from Florida Keys to Chicago (CHI)
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 2/20. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
Mar 18 — Mar 251
1 adult, Economy
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Find cheap flights from Florida Keys to Chicago 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
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Florida Keys to Chicago
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Cheapest flights from Florida Keys to ChicagoExplore the most affordable flight options available from Florida Keys to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 16, 2026.
Explore the most affordable flight options available from Florida Keys to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 16, 2026.
This Super.com deal was found by Cheapflights users on 2/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2012:40 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Mon 2/2311:33 am
ORD
- MIA
Nonstop3h 15m
Frontier
Deal found 2/16![Frontier logo]()
$71
This Kiwi.com deal was found by Cheapflights users on 2/14. 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 2/277:00 am
MIA
- ORD
Nonstop3h 38m
Multiple Airlines
Tue 3/37:23 pm
ORD
- MIA
Nonstop3h 16m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$72
This Flightnetwork deal was found by Cheapflights users on 2/16. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/277:00 am
MIA
- ORD
Nonstop3h 38m
Multiple Airlines
Sun 3/17:23 pm
ORD
- MIA
Nonstop3h 16m
Multiple Airlines
Deal found 2/16![Multiple Airlines logo]()
$73
This Cheapflightsfares deal was found by Cheapflights users on 2/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/1312:45 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Mon 3/169:50 am
ORD
- MIA
Nonstop3h 15m
Frontier
Deal found 2/13![Frontier logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 2/16. 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.
Thu 3/2611:13 am
MIA
- MDW
Nonstop3h 28m
Frontier
Mon 3/309:42 pm
MDW
- MIA
Nonstop3h 08m
Frontier
Deal found 2/16![Frontier logo]()
$74
This Cheapflightsfares deal was found by Cheapflights users on 2/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/77:15 am
MIA
- ORD
Nonstop3h 38m
Frontier
Mon 3/99:05 pm
ORD
- MIA
Nonstop3h 15m
Frontier
Deal found 2/15![Frontier logo]()
$75
This Spirit deal was found by Cheapflights users on 2/13. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:12 am
MIA
- ORD
Nonstop3h 27m
Spirit Airlines
Sun 3/87:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 2/14. 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.
Sat 2/288:00 am
MIA
- ORD
Nonstop3h 38m
Multiple Airlines
Sun 3/19:18 am
ORD
- MIA
Nonstop3h 18m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$77
This Expedia deal was found by Cheapflights users on 2/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/239:21 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Sun 4/263:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Deal found 2/14![Frontier logo]()
$78
This Flightnetwork deal was found by Cheapflights users on 2/14. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/263:50 pm
MIA
- ORD
Nonstop3h 28m
Spirit Airlines
Sun 3/19:18 am
ORD
- MIA
Nonstop3h 18m
Spirit Airlines
Deal found 2/14![Spirit Airlines logo]()
$79
This Super.com deal was found by Cheapflights users on 2/13. 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.
Fri 3/611:13 am
MIA
- MDW
Nonstop3h 28m
Frontier
Mon 3/96:00 am
MDW
- MIA
Nonstop3h 13m
Frontier
Deal found 2/13![Frontier logo]()
$79
This Booking.com deal was found by Cheapflights users on 2/13. 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.
Sat 3/146:00 am
MIA
- ORD
Nonstop3h 25m
Spirit Airlines
Mon 3/164:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$80
Best flights from Florida Keys to ChicagoDiscover carefully curated flight deals from Florida Keys to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 16, 2026.
Discover carefully curated flight deals from Florida Keys to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 16, 2026.
This Priceline deal was found by Cheapflights users on 2/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/263:50 pm
MIA
- ORD
Nonstop3h 28m
Multiple Airlines
Mon 3/211:33 am
ORD
- MIA
Nonstop3h 15m
Multiple Airlines
Deal found 2/16![Multiple Airlines logo]()
$73
This Spirit deal was found by Cheapflights users on 2/14. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/77:12 am
MIA
- ORD
Nonstop3h 27m
Spirit Airlines
Sun 3/87:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Deal found 2/14![Spirit Airlines logo]()
$80
This United Airlines deal was found by Cheapflights users on 2/14. 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.
Thu 4/307:25 pm
MIA
- ORD
Nonstop3h 40m
United Airlines
Sun 5/310:35 am
ORD
- MIA
Nonstop3h 22m
United Airlines
Deal found 2/14![United Airlines logo]()
$111
This Cheapflightsfares deal was found by Cheapflights users on 2/16. 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 4/199:21 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Sat 4/253:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Deal found 2/16![Frontier logo]()
$118
This Southwest deal was found by Cheapflights users on 2/14. 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.
Thu 4/236:05 am
MIA
- MDW
Nonstop3h 15m
Southwest
Mon 4/276:50 pm
MDW
- MIA
Nonstop3h 00m
Southwest
Deal found 2/14![Southwest logo]()
$153
This Spirit deal was found by Cheapflights users on 2/13. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:12 am
MIA
- ORD
Nonstop3h 27m
Spirit Airlines
Sun 3/17:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$82
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:00 am
MIA
- MDW
1 stop4h 54m
Delta
Mon 3/91:10 pm
MDW
- MIA
1 stop7h 08m
Delta
Deal found 2/12![Delta logo]()
$217
This CheapOair deal was found by Cheapflights users on 2/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/136:00 am
MIA
- ORD
Nonstop3h 25m
Spirit Airlines
Mon 3/164:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Deal found 2/16![Spirit Airlines logo]()
$100
This Spirit deal was found by Cheapflights users on 2/15. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/207:12 am
MIA
- ORD
Nonstop3h 27m
Spirit Airlines
Sun 2/229:18 am
ORD
- MIA
Nonstop3h 18m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$104
This Frontier deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/611:13 am
MIA
- MDW
Nonstop3h 28m
Frontier
Mon 3/92:41 pm
MDW
- MIA
1 stop9h 06m
Frontier
Deal found 2/12![Frontier logo]()
$133
This American Airlines deal was found by Cheapflights users on 2/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:53 pm
EYW
- ORD
Nonstop3h 47m
American Airlines
Tue 3/101:53 pm
ORD
- EYW
Nonstop3h 26m
American Airlines
Deal found 2/16![American Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1211:13 am
MIA
- MDW
Nonstop3h 28m
Frontier
Thu 3/196:44 pm
MDW
- MIA
1 stop17h 00m
Frontier
Deal found 2/12![Frontier logo]()
$136
This Cheapflightsfares deal was found by Cheapflights users on 2/16. 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.
Tue 3/174:06 pm
MIA
- ORD
Nonstop3h 25m
Spirit Airlines
Tue 3/244:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Deal found 2/16![Spirit Airlines logo]()
$119
This Spirit deal was found by Cheapflights users on 2/16. 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.
Wed 3/47:12 am
MIA
- ORD
Nonstop3h 27m
Spirit Airlines
Sun 3/87:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Deal found 2/16![Spirit Airlines logo]()
$120
This Southwest deal was found by Cheapflights users on 2/15. 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.
Thu 4/166:05 am
MIA
- MDW
Nonstop3h 15m
Southwest
Mon 4/208:10 am
MDW
- MIA
Nonstop3h 00m
Southwest
Deal found 2/15![Southwest logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 2/16. 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.
Thu 3/511:01 am
EYW
- ORD
1 stop9h 36m
Multiple Airlines
Tue 3/102:43 pm
ORD
- EYW
1 stop20h 07m
Multiple Airlines
Deal found 2/16![Multiple Airlines logo]()
$211
This Southwest deal was found by Cheapflights users on 2/14. 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 3/206:40 am
MIA
- MDW
Nonstop3h 15m
Southwest
Mon 3/237:30 pm
MDW
- MIA
Nonstop3h 00m
Southwest
Deal found 2/14![Southwest logo]()
$195
This WAYA deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/1311:13 am
MIA
- MDW
Nonstop3h 28m
Frontier
Tue 3/176:00 am
MDW
- MIA
1 stop5h 46m
Frontier
Deal found 2/12![Frontier logo]()
$186
This Southwest deal was found by Cheapflights users on 2/15. 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.
Fri 4/176:05 am
MIA
- MDW
Nonstop3h 15m
Southwest
Sun 4/196:45 pm
MDW
- MIA
Nonstop3h 00m
Southwest
Deal found 2/15![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 2/15. 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.
Thu 4/166:05 pm
MIA
- MDW
Nonstop3h 20m
Southwest
Sun 4/196:45 pm
MDW
- MIA
Nonstop3h 00m
Southwest
Deal found 2/15![Southwest logo]()
$207
This United Airlines deal was found by Cheapflights users on 2/13. 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.
Sat 5/164:47 pm
EYW
- ORD
1 stop8h 58m
United Airlines
Mon 5/1810:43 am
ORD
- EYW
Nonstop3h 24m
United Airlines
Deal found 2/13![United Airlines logo]()
$278
This American Airlines deal was found by Cheapflights users on 2/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/187:45 am
EYW
- ORD
1 stop7h 31m
American Airlines
Tue 3/241:53 pm
ORD
- EYW
Nonstop3h 26m
American Airlines
Deal found 2/13![American Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 2/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/21:06 pm
EYW
- ORD
1 stop27h 46m
Multiple Airlines
Fri 3/65:58 pm
ORD
- EYW
2 stops37h 08m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$276
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/16:30 am
MIA
- MDW
Nonstop3h 15m
Southwest
Sat 4/47:00 pm
MDW
- MIA
Nonstop3h 00m
Southwest
Deal found 2/12![Southwest logo]()
$208
This American Airlines deal was found by Cheapflights users on 2/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:46 pm
EYW
- ORD
Nonstop3h 49m
American Airlines
Mon 4/138:39 am
ORD
- EYW
1 stop6h 01m
American Airlines
Deal found 2/14![American Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 2/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:10 am
EYW
- MDW
1 stop5h 49m
Delta
Sat 2/286:00 am
MDW
- EYW
1 stop6h 48m
Delta
Deal found 2/14![Delta logo]()
$509
This Delta deal was found by Cheapflights users on 2/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/97:30 am
EYW
- MDW
1 stop5h 32m
Delta
Mon 4/1312:53 pm
MDW
- EYW
1 stop5h 47m
Delta
Deal found 2/13![Delta logo]()
$553
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/182:44 pm
EYW
- MDW
2 stops30h 22m
Multiple Airlines
Sun 7/267:41 pm
MDW
- EYW
1 stop14h 49m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$524
This Delta deal was found by Cheapflights users on 2/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/311:48 am
EYW
- MDW
1 stop5h 29m
Delta
Mon 6/81:05 pm
MDW
- EYW
1 stop5h 39m
Delta
Deal found 2/13![Delta logo]()
$594
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/182:44 pm
EYW
- RFD
2 stops22h 40m
Multiple Airlines
Sun 7/2611:27 am
RFD
- EYW
1 stop25h 03m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$736
Last-minute flights from Florida Keys to ChicagoDiscover last-minute flight deals from Florida Keys to Chicago. Data last updated February 16, 2026 and is based on user searches.
Discover last-minute flight deals from Florida Keys to Chicago. Data last updated February 16, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 2/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2012:40 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Mon 2/2311:33 am
ORD
- MIA
Nonstop3h 15m
Frontier
Deal found 2/16![Frontier logo]()
$71
This CheapOair deal was found by Cheapflights users on 2/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2012:40 pm
MIA
- ORD
Nonstop3h 38m
Multiple Airlines
Mon 2/237:23 pm
ORD
- MIA
Nonstop3h 16m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$78
This Flightnetwork deal was found by Cheapflights users on 2/14. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/263:50 pm
MIA
- ORD
Nonstop3h 28m
Spirit Airlines
Sun 3/19:18 am
ORD
- MIA
Nonstop3h 18m
Spirit Airlines
Deal found 2/14![Spirit Airlines logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 2/14. 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 2/277:00 am
MIA
- ORD
Nonstop3h 38m
Multiple Airlines
Tue 3/37:23 pm
ORD
- MIA
Nonstop3h 16m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$72
This Booking.com deal was found by Cheapflights users on 2/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/277:12 am
MIA
- ORD
Nonstop3h 27m
Multiple Airlines
Mon 3/211:33 am
ORD
- MIA
Nonstop3h 15m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$73
This Kiwi.com deal was found by Cheapflights users on 2/14. 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.
Sat 2/288:00 am
MIA
- ORD
Nonstop3h 38m
Multiple Airlines
Tue 3/37:23 pm
ORD
- MIA
Nonstop3h 16m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$77
This Spirit deal was found by Cheapflights users on 2/13. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:12 am
MIA
- ORD
Nonstop3h 27m
Spirit Airlines
Sun 3/87:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$76
This Super.com deal was found by Cheapflights users on 2/13. 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.
Fri 3/611:13 am
MIA
- MDW
Nonstop3h 28m
Frontier
Mon 3/96:00 am
MDW
- MIA
Nonstop3h 13m
Frontier
Deal found 2/13![Frontier logo]()
$79
This Expedia deal was found by Cheapflights users on 2/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/77:12 am
MIA
- ORD
Nonstop3h 27m
Spirit Airlines
Mon 3/97:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$75
This Cheapflightsfares deal was found by Cheapflights users on 2/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/1312:45 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Mon 3/169:50 am
ORD
- MIA
Nonstop3h 15m
Frontier
Deal found 2/13![Frontier logo]()
$74
This Cheapflightsfares deal was found by Cheapflights users on 2/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/147:15 am
MIA
- ORD
Nonstop3h 38m
Frontier
Mon 3/169:50 am
ORD
- MIA
Nonstop3h 15m
Frontier
Deal found 2/13![Frontier logo]()
$80
This Kiwi.com deal was found by Cheapflights users on 2/16. 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.
Thu 3/2611:13 am
MIA
- MDW
Nonstop3h 28m
Frontier
Mon 3/309:42 pm
MDW
- MIA
Nonstop3h 08m
Frontier
Deal found 2/16![Frontier logo]()
$74
One-way flights from Florida Keys to ChicagoSearch for one-way flight options from Florida Keys to Chicago. Find affordable one-way fares based on user searches. Data last updated February 16, 2026.
Search for one-way flight options from Florida Keys to Chicago. Find affordable one-way fares based on user searches. Data last updated February 16, 2026.
This Super.com deal was found by Cheapflights users on 2/15. 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.
Fri 2/207:12 am
MIA
- ORD
Nonstop3h 27m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$55
This CheapOair deal was found by Cheapflights users on 2/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:28 am
MIA
- MDW
Nonstop3h 28m
Frontier
Deal found 2/16![Frontier logo]()
$55
This American Airlines deal was found by Cheapflights users on 2/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1510:00 pm
MIA
- ORD
Nonstop3h 25m
American Airlines
Deal found 2/15![American Airlines logo]()
$56
This Southwest deal was found by Cheapflights users on 2/15. 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.
Fri 5/16:05 am
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 2/15![Southwest logo]()
$56
This American Airlines deal was found by Cheapflights users on 2/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/178:40 pm
MIA
- ORD
Nonstop3h 37m
American Airlines
Deal found 2/15![American Airlines logo]()
$57
This Super.com deal was found by Cheapflights users on 2/13. 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.
Wed 4/87:20 am
MIA
- ORD
Nonstop3h 30m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$59
This Cheapflightsfares deal was found by Cheapflights users on 2/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:00 am
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 2/13![Frontier logo]()
$60
This Super.com deal was found by Cheapflights users on 2/15. 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.
Sun 5/39:21 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 2/15![Frontier logo]()
$63
This Kiwi.com deal was found by Cheapflights users on 2/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/78:08 pm
MIA
- ORD
1 stop13h 35m
Frontier
Deal found 2/15![Frontier logo]()
$64
This Super.com deal was found by Cheapflights users on 2/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/249:45 pm
MIA
- ORD
1 stop12h 05m
Spirit Airlines
Deal found 2/16![Spirit Airlines logo]()
$65
This Cheapflightsfares deal was found by Cheapflights users on 2/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/177:00 am
MIA
- ORD
1 stop8h 20m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$66
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:00 am
MIA
- ORD
1 stop13h 29m
Frontier
Deal found 2/13![Frontier logo]()
$68
Find flight deals from Florida Keys to Chicago
Keep the following information in mind while searching for Florida Keys to Chicago flight deals. Data was last updated February 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $72 (Kiwi.com) |
One-way from | $55 (Super.com) |
Cheapflights Fare Finder
Customize your flight search to find flights from Florida Keys to Chicago 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 February 16, 2026.
Use the filters below to find and compare flights from Florida Keys to Chicago that are best for you.
Fly from
Florida Keys
Fly to
Chicago
Route
Depart
Return
Price
MiamiChicago
MIA - ORD
MIAORD
Miami
Thu 2/26
3:50 pm-6:18 pm
Nonstop3h 28m
Chicago O'Hare Intl
Mon 3/2
11:33 am-3:48 pm
Nonstop3h 15m
$73
MiamiChicago
MIA - ORD
MIAORD
Miami
Sat 3/7
7:12 am-9:39 am
Nonstop3h 27m
Chicago O'Hare Intl
Sun 3/8
7:23 pm-11:39 pm
Nonstop3h 16m
$80
MiamiChicago
MIA - ORD
MIAORD
Miami
Thu 2/26
7:12 am-9:39 am
Nonstop3h 27m
Chicago O'Hare Intl
Sun 3/1
7:23 pm-11:39 pm
Nonstop3h 16m
$82
MiamiChicago
MIA - ORD
MIAORD
Miami
Fri 3/13
6:00 am-8:25 am
Nonstop3h 25m
Chicago O'Hare Intl
Mon 3/16
4:51 pm-8:57 pm
Nonstop3h 06m
$100
MiamiChicago
MIA - ORD
MIAORD
Miami
Fri 2/20
7:12 am-9:39 am
Nonstop3h 27m
Chicago O'Hare Intl
Sun 2/22
9:18 am-1:36 pm
Nonstop3h 18m
$104
MiamiChicago
MIA - ORD
MIAORD
Miami
Thu 4/30
7:25 pm-10:05 pm
Nonstop3h 40m
Chicago O'Hare Intl
Sun 5/3
10:35 am-2:57 pm
Nonstop3h 22m
$111
MiamiChicago
MIA - ORD
MIAORD
Miami
Sun 4/19
9:21 pm-11:59 pm
Nonstop3h 38m
Chicago O'Hare Intl
Sat 4/25
3:52 pm-8:11 pm
Nonstop3h 19m
$118
MiamiChicago
MIA - ORD
MIAORD
Miami
Tue 3/17
4:06 pm-6:31 pm
Nonstop3h 25m
Chicago O'Hare Intl
Tue 3/24
4:51 pm-8:57 pm
Nonstop3h 06m
$119
MiamiChicago
MIA - ORD
MIAORD
Miami
Wed 3/4
7:12 am-9:39 am
Nonstop3h 27m
Chicago O'Hare Intl
Sun 3/8
7:23 pm-11:39 pm
Nonstop3h 16m
$120
MiamiChicago
MIA - MDW
MIAMDW
Miami
Fri 3/6
11:13 am-1:41 pm
Nonstop3h 28m
Chicago Midway
Mon 3/9
2:41 pm-12:47 am
1 stop9h 06m
$133
Showing 1-10 of 60 results
Best time to book a flight from Florida Keys to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Florida Keys with our price prediction graph.
MIA-ORD
MIA-MDW
EYW-ORD
EYW-MDW
EYW-RFD
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 Florida Keys to Chicago
zzEOA-CHI
MIA-ORD
MIA-MDW
EYW-ORD
EYW-MDW
What is the cheapest time of day to fly from EOA to CHI?
Find hourly flight availability from Florida Keys to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 16, 2026.
When flying from Florida Keys to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Florida Keys to Chicago
Explore weekly flight availability from Florida Keys to Chicago. 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 February 16, 2026.
The most flights from zzEOA to CHI are scheduled on a Monday (7 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated February 16, 2026.
Get a feel of what it's like to fly with Southwest, United Airlines, and American Airlines from Florida Keys to Chicago by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Related info for your journey
Find useful and relevant information for your journey from Florida Keys to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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Alternative routes for Florida Keys to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on February 16, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Florida Keys to Chicago by cabin class
Find flights from Florida Keys to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Florida Keys and Chicago flights
Browse other Florida Keys and Chicago flight options. Last updated on February 16, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Florida Keys to Chicago flights
Consider these flights traveling from Florida Keys to Chicago.
Top 2 airlines flying from Florida Keys to Chicago
Discover the top 2 airlines that operate flights from Florida Keys to Chicago. 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 February 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$249 | Average$364 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$309 | Average$457 | FlexibilityNo cancel fee | On-time71% |