$114+ Cheap flights from Key West (EYW) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
Oct 20 — Oct 271
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Key West 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
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.Cheap flight deals from Key West to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Key West to ChicagoExplore the most affordable flight options available from Key West to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 20, 2026.
Explore the most affordable flight options available from Key West to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:34 am -
1 stop24h 17m
Fri 10/237:44 pm -
2 stops38h 37m
Deal found 9/18![Multiple Airlines logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Sat 10/1710:04 am -
2 stops9h 27m
Sat 10/319:51 am -
1 stop24h 28m
Deal found 9/16![Multiple Airlines logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Fri 10/1610:59 am -
1 stop21h 52m
Tue 10/208:04 am -
2 stops24h 20m
Deal found 9/17![Multiple Airlines logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Fri 10/1610:14 am -
1 stop6h 26m
Tue 10/206:21 am -
2 stops26h 03m
Deal found 9/17![Multiple Airlines logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/2912:01 pm -
2 stops11h 42m
Sat 10/319:51 am -
1 stop26h 47m
Deal found 9/19![Multiple Airlines logo]()
$353
This American Airlines deal was found by Cheapflights users on 9/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:49 pm -
Nonstop3h 55m
Mon 12/712:10 pm -
Nonstop3h 22m
Deal found 9/17![American Airlines logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/310:04 am -
2 stops48h 16m
Wed 10/73:50 pm -
1 stop17h 29m
Deal found 9/17![Multiple Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Fri 10/28:34 am -
1 stop15h 25m
Tue 10/67:11 am -
2 stops25h 13m
Deal found 9/17![Multiple Airlines logo]()
$370
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/410:59 am -
2 stops32h 24m
Wed 10/73:50 pm -
1 stop17h 29m
Deal found 9/17![Multiple Airlines logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Thu 10/110:59 am -
1 stop13h 00m
Tue 10/67:11 am -
2 stops25h 13m
Deal found 9/17![Multiple Airlines logo]()
$376
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/410:59 am -
1 stop13h 00m
Tue 10/67:11 am -
2 stops25h 13m
Deal found 9/17![Multiple Airlines logo]()
$378
This American Airlines deal was found by Cheapflights users on 9/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/161:43 pm -
1 stop7h 12m
Tue 10/208:05 am -
1 stop5h 31m
Deal found 9/17![American Airlines logo]()
$379
Best flights from Key West to ChicagoDiscover carefully curated flight deals from Key West to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 20, 2026.
Discover carefully curated flight deals from Key West to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 20, 2026.
This American Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:56 pm -
1 stop5h 40m
Mon 12/78:05 am -
1 stop6h 01m
Deal found 9/20![American Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 9/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/52:06 pm -
1 stop5h 59m
Mon 12/75:30 am -
1 stop6h 41m
Deal found 9/17![Delta logo]()
$379
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/294:10 pm -
Nonstop3h 50m
Sun 11/111:00 am -
Nonstop3h 29m
Deal found 9/15![United Airlines logo]()
$517
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Thu 10/291:43 pm -
1 stop7h 12m
Sun 11/16:59 am -
1 stop8h 15m
Deal found 9/15![American Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 9/16. 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.
Thu 11/126:05 pm -
1 stop5h 49m
Tue 11/1711:27 am -
1 stop7h 33m
Deal found 9/16![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 9/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/22:00 pm -
1 stop7h 56m
Tue 10/61:23 pm -
1 stop5h 38m
Deal found 9/17![Delta logo]()
$439
This American Airlines deal was found by Cheapflights users on 9/15. 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 9/301:47 pm -
1 stop5h 20m
Sun 10/45:00 am -
1 stop7h 17m
Deal found 9/15![American Airlines logo]()
$439
This Delta deal was found by Cheapflights users on 9/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:10 pm -
1 stop5h 23m
Tue 10/2012:49 pm -
1 stop6h 12m
Deal found 9/17![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 9/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:40 am -
1 stop5h 00m
Tue 10/610:59 am -
1 stop5h 16m
Deal found 9/17![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 9/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/111:42 am -
1 stop5h 55m
Sun 10/46:40 am -
1 stop5h 13m
Deal found 9/17![Delta logo]()
$469
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/174:20 pm -
Nonstop3h 39m
Sat 10/3110:58 am -
Nonstop3h 31m
Deal found 9/16![United Airlines logo]()
$730
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:19 pm -
1 stop5h 25m
Sun 10/46:05 am -
1 stop5h 48m
Deal found 9/15![Delta logo]()
$469
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 9/302:00 pm -
1 stop7h 56m
Sun 10/46:40 am -
1 stop5h 13m
Deal found 9/19![Delta logo]()
$475
This American Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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.
Mon 10/510:24 am -
1 stop6h 07m
Fri 10/98:43 am -
1 stop7h 15m
Deal found 9/19![American Airlines logo]()
$807
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 9/3011:42 am -
1 stop5h 55m
Sat 10/310:44 am -
1 stop5h 39m
Deal found 9/19![Delta logo]()
$505
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:06 pm -
1 stop5h 48m
Mon 12/79:37 am -
2 stops9h 24m
Deal found 9/20![Delta logo]()
$719
This Delta deal was found by Cheapflights users on 9/16. 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.
Thu 10/111:42 am -
2 stops7h 51m
Mon 10/51:00 pm -
1 stop6h 00m
Deal found 9/16![Delta logo]()
$749
This Delta deal was found by Cheapflights users on 9/16. 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.
Sat 10/176:11 pm -
1 stop5h 22m
Sat 10/316:04 am -
1 stop7h 16m
Deal found 9/16![Delta logo]()
$844
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:40 am -
2 stops11h 20m
Sun 11/19:29 am -
2 stops6h 46m
Deal found 9/15![Delta logo]()
$969
Last-minute flights from Key West to ChicagoDiscover last-minute flight deals from Key West to Chicago. Data last updated September 20, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to Chicago. Data last updated September 20, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Thu 10/110:59 am -
1 stop13h 00m
Tue 10/67:11 am -
2 stops25h 13m
Deal found 9/17![Multiple Airlines logo]()
$376
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/110:59 am -
1 stop13h 00m
Mon 10/510:26 am -
2 stops25h 10m
Deal found 9/16![Multiple Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Fri 10/28:34 am -
1 stop15h 25m
Tue 10/67:11 am -
2 stops25h 13m
Deal found 9/17![Multiple Airlines logo]()
$370
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/310:04 am -
2 stops48h 16m
Wed 10/73:50 pm -
1 stop17h 29m
Deal found 9/17![Multiple Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/410:59 am -
2 stops32h 24m
Wed 10/73:50 pm -
1 stop17h 29m
Deal found 9/17![Multiple Airlines logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:34 am -
1 stop24h 17m
Fri 10/237:44 pm -
2 stops38h 37m
Deal found 9/18![Multiple Airlines logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Fri 10/1610:59 am -
1 stop21h 52m
Tue 10/208:04 am -
2 stops24h 20m
Deal found 9/17![Multiple Airlines logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Fri 10/1610:14 am -
1 stop6h 26m
Tue 10/206:21 am -
2 stops26h 03m
Deal found 9/17![Multiple Airlines logo]()
$337
This American Airlines deal was found by Cheapflights users on 9/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/161:43 pm -
1 stop7h 12m
Tue 10/208:05 am -
1 stop5h 31m
Deal found 9/17![American Airlines logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Sat 10/1710:04 am -
2 stops9h 27m
Sat 10/319:51 am -
1 stop24h 28m
Deal found 9/16![Multiple Airlines logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/2912:01 pm -
2 stops11h 42m
Sat 10/319:51 am -
1 stop26h 47m
Deal found 9/19![Multiple Airlines logo]()
$353
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Thu 10/291:43 pm -
1 stop7h 12m
Sun 11/112:10 pm -
Nonstop3h 22m
Deal found 9/15![American Airlines logo]()
$369
One-way flights from Key West to ChicagoSearch for one-way flight options from Key West to Chicago. Find affordable one-way fares based on user searches. Data last updated September 20, 2026.
Search for one-way flight options from Key West to Chicago. Find affordable one-way fares based on user searches. Data last updated September 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Wed 10/2110:04 am -
2 stops9h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Sat 11/1410:04 am -
2 stops9h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 1/612:19 pm -
1 stop21h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Tue 10/201:16 pm -
2 stops30h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Thu 10/228:36 pm -
1 stop12h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Allegiant Air logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1510:59 am -
1 stop23h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Wed 10/2110:04 am -
2 stops23h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Tue 10/61:16 pm -
2 stops29h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Wed 10/1410:04 am -
2 stops9h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/171:16 pm -
2 stops30h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/2410:04 am -
2 stops14h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Wed 10/2110:04 am -
2 stops14h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$132
Find flight deals from Key West to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Key West (EYW) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $249 (Kiwi.com) |
One-way from | $114 (Kiwi.com) |
Good round-trip deal | $339 or less |
Good one-way deal | $293 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Key West 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 7,457,451 searches. Data last updated September 20, 2026.
Use the filters below to find and compare flights from Key West to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Key WestChicago
EYW Key West - RFD Chicago Greater Rockford
EYWRFD
Key West
Thu 10/22
8:36 pm-7:54 am
1 stop12h 18m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$124
Key WestChicago
EYW Key West - RFD Chicago Greater Rockford
EYWRFD
Key West
Wed 10/21
10:04 am-8:50 am
2 stops23h 46m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$127
Key WestChicago
EYW Key West - RFD Chicago Greater Rockford
EYWRFD
Key West
Sat 10/24
10:04 am-9:30 am
2 stops24h 26m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
Key WestChicago
EYW Key West - RFD Chicago Greater Rockford
EYWRFD
Key West
Fri 10/23
2:03 pm-7:06 pm
1 stop6h 03m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$160
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Tue 12/1
5:05 pm-8:01 pm
Nonstop3h 56m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$214
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Wed 3/17
5:45 pm-8:40 pm
Nonstop3h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$309
Quickest round-trip
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Fri 12/18
5:52 pm-8:40 pm
Nonstop3h 48m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$309
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Tue 11/17
6:05 pm-11:54 pm
1 stop6h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$319
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Sat 10/17
11:38 am-4:58 pm
1 stop6h 20m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$319
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Sat 11/14
6:05 pm-11:54 pm
1 stop6h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$319
Showing 1-10 of 39 resultsSorted by cheapest first
Compare providers for flights from Key West to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Key West to Chicago in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Key West-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Key West-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Key West-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Key West-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Key West-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Key West to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Key West with our price prediction graph.
EYW-CHI
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 Key West to Chicago
EYW-CHI
EYW-ORD
EYW-MDW
EYW-RFD
No data available for this route at this time. Please check back soon.
The best insider tips for Key West to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Key West to Chicago trip
Our travel experts
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 September 20, 2026.
See what other customers who have flown with American Airlines from Key West to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
7.9
Boarding
7.4
Entertainment
6.8
Comfort
7.2
Food
6.4
Overall
7.0
Reviews
1 / 20
2.0
MediocreAnonymous,Aug 2025
BNA - ORD
Crew
7.9
Boarding
7.4
Entertainment
6.8
Comfort
7.2
Food
6.4
Overall
7.0
Reviews
1 / 20
2.0
MediocreAnonymous,Aug 2025
BNA - ORD
Related info for your journey
Find useful and relevant information for your journey from Key West 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 locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Key West
Popular flights
Top destinations
Alternative routes for Key West 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 September 20, 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 Key West to Chicago by cabin class
Find flights from Key West to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Key West and Chicago flights
Browse other Key West and Chicago flight options. Last updated on September 20, 2026.
Other flights from Key West
Browse through other flights departing from Key West. Flights are based on user searches made on Cheapflights and were last updated on September 20, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Key West to Chicago flights
Consider these flights traveling from Key West to Chicago.
Top airline flying from Key West to Chicago
Discover the top airline that operate flights from Key West 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 7,457,451 searches. Data last updated September 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$319 | Average$409 | FlexibilityNo cancel fee | On-time71% |