$125+ Cheap flights from Chicago (CHI) to Key West (EYW)
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 11/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EYW
Sep 27 — Oct 41
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Key West 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 West are usually found in June or July, booked 70 days in advance, depart on a Tuesday or Monday and return on a Wednesday
Cheap flight deals from Chicago to Key West
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Cheapest flights from Chicago to Key WestExplore the most affordable flight options available from Chicago to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 28, 2026.
Explore the most affordable flight options available from Chicago to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:50 pm -
1 stop14h 54m
Mon 10/510:59 am -
1 stop13h 00m
Deal found 8/25![Multiple Airlines logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/33:50 pm -
1 stop21h 23m
Wed 10/710:04 am -
2 stops9h 19m
Deal found 8/27![Multiple Airlines logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/33:50 pm -
1 stop17h 29m
Tue 10/61:16 pm -
2 stops23h 35m
Deal found 8/27![Multiple Airlines logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/149:51 am -
1 stop26h 05m
Fri 11/204:06 pm -
2 stops33h 10m
Deal found 8/23![Multiple Airlines logo]()
$288
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/249:00 am -
1 stop24h 19m
Thu 10/2912:01 pm -
2 stops11h 42m
Deal found 8/27![Multiple Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/138:04 am -
2 stops24h 20m
Sun 10/1810:59 am -
1 stop21h 32m
Deal found 8/26![Multiple Airlines logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/32:31 pm -
1 stop18h 48m
Wed 12/910:45 am -
1 stop24h 03m
Deal found 8/24![Multiple Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/168:04 am -
2 stops24h 20m
Mon 10/1910:59 am -
1 stop21h 52m
Deal found 8/27![Multiple Airlines logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:00 am -
2 stops24h 47m
Sun 10/188:41 pm -
1 stop11h 50m
Deal found 8/25![Multiple Airlines logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:25 am -
2 stops24h 59m
Mon 10/510:59 am -
1 stop13h 00m
Deal found 8/25![Multiple Airlines logo]()
$308
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/612:49 pm -
1 stop6h 12m
Tue 10/136:10 pm -
1 stop5h 23m
Deal found 8/23![Delta logo]()
$331
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1011:27 am -
1 stop4h 43m
Sat 11/146:05 pm -
1 stop5h 49m
Deal found 8/24![Delta logo]()
$339
Best flights from Chicago to Key WestDiscover carefully curated flight deals from Chicago to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 28, 2026.
Discover carefully curated flight deals from Chicago to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 28, 2026.
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/306:49 am -
1 stop5h 10m
Wed 12/96:06 pm -
1 stop6h 46m
Deal found 8/24![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/66:00 am -
1 stop6h 29m
Sat 10/104:00 pm -
Nonstop2h 27m
Deal found 8/26![United Airlines logo]()
$517
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/49:56 am -
1 stop6h 15m
Wed 12/96:06 pm -
2 stops17h 53m
Deal found 8/24![Delta logo]()
$434
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/31:02 pm -
1 stop6h 00m
Tue 12/87:25 am -
1 stop5h 40m
Deal found 8/25![Delta logo]()
$478
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/711:28 am -
1 stop4h 43m
Sat 12/126:06 pm -
1 stop5h 49m
Deal found 8/27![Delta logo]()
$479
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/16:25 pm -
2 stops16h 42m
Sat 1/96:20 pm -
1 stop5h 55m
Deal found 8/25![United Airlines logo]()
$736
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/311:35 am -
1 stop7h 25m
Tue 10/66:10 pm -
1 stop5h 23m
Deal found 8/27![Delta logo]()
$568
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:05 am -
1 stop5h 48m
Tue 9/226:19 pm -
1 stop5h 25m
Deal found 8/25![Delta logo]()
$574
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 12/196:20 pm -
2 stops19h 03m
Thu 12/241:35 pm -
1 stop6h 15m
Deal found 8/27![United Airlines logo]()
$770
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/911:27 am -
1 stop4h 43m
Thu 11/127:25 am -
1 stop5h 34m
Deal found 8/25![Delta logo]()
$617
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/317:00 am -
Nonstop3h 41m
Mon 1/44:04 pm -
Nonstop3h 49m
Deal found 8/25![United Airlines logo]()
$839
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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.
Mon 10/53:35 pm -
2 stops20h 54m
Thu 10/82:15 pm -
2 stops18h 10m
Deal found 8/26![United Airlines logo]()
$892
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/16:00 am -
1 stop7h 01m
Wed 1/66:00 pm -
1 stop5h 10m
Deal found 8/24![Delta logo]()
$671
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/169:40 pm -
2 stops14h 49m
Wed 9/232:20 pm -
2 stops16h 37m
Deal found 8/27![United Airlines logo]()
$908
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/29:58 am -
1 stop6h 26m
Wed 1/611:45 am -
1 stop5h 40m
Deal found 8/23![Delta logo]()
$684
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/612:49 pm -
1 stop6h 12m
Tue 10/137:40 am -
2 stops10h 07m
Deal found 8/23![Delta logo]()
$695
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/149:30 am -
2 stops9h 30m
Wed 11/186:05 pm -
1 stop5h 49m
Deal found 8/27![Delta logo]()
$699
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:49 am -
1 stop5h 22m
Sat 12/127:25 am -
2 stops7h 34m
Deal found 8/27![Delta logo]()
$699
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 1/79:30 am -
2 stops6h 41m
Thu 1/146:00 pm -
1 stop5h 10m
Deal found 8/26![Delta logo]()
$723
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/310:55 am -
2 stops8h 06m
Sat 11/76:11 pm -
1 stop6h 46m
Deal found 8/24![Delta logo]()
$730
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/219:30 am -
2 stops9h 30m
Tue 11/246:05 pm -
1 stop5h 49m
Deal found 8/24![Delta logo]()
$750
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2111:10 am -
1 stop7h 33m
Sun 1/2411:45 am -
2 stops9h 52m
Deal found 8/23![Delta logo]()
$763
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/285:30 am -
1 stop6h 38m
Sun 1/317:00 am -
2 stops10h 37m
Deal found 8/23![Delta logo]()
$769
Last-minute flights from Chicago to Key WestDiscover last-minute flight deals from Chicago to Key West. Data last updated August 28, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Key West. Data last updated August 28, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:59 pm -
1 stop16h 26m
Mon 8/3112:07 pm -
1 stop12h 01m
Deal found 8/25![Multiple Airlines logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/93:50 pm -
1 stop18h 45m
Sat 9/1210:04 am -
2 stops9h 19m
Deal found 8/27![Multiple Airlines logo]()
$342
This American Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:29 am -
1 stop7h 20m
Tue 9/227:47 pm -
1 stop5h 46m
Deal found 8/23![American Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:29 am -
1 stop5h 42m
Wed 9/2311:30 am -
1 stop7h 37m
Deal found 8/25![American Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/161:00 pm -
1 stop6h 00m
Tue 9/226:19 pm -
1 stop5h 25m
Deal found 8/26![Delta logo]()
$359
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/225:00 am -
1 stop4h 57m
Mon 9/286:27 pm -
1 stop6h 32m
Deal found 8/26![American Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2310:05 am -
1 stop8h 12m
Tue 9/291:47 pm -
1 stop5h 20m
Deal found 8/23![American Airlines logo]()
$323
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2310:48 am -
1 stop5h 35m
Tue 9/296:19 pm -
1 stop5h 25m
Deal found 8/23![Delta logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/243:50 pm -
1 stop17h 29m
Thu 10/110:59 am -
1 stop13h 00m
Deal found 8/24![Multiple Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/243:50 pm -
1 stop17h 29m
Mon 9/2810:59 am -
1 stop13h 00m
Deal found 8/26![Multiple Airlines logo]()
$347
This American Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2611:50 am -
1 stop5h 05m
Tue 9/297:47 pm -
1 stop5h 46m
Deal found 8/23![American Airlines logo]()
$355
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:05 am -
1 stop5h 48m
Tue 9/296:19 pm -
1 stop5h 25m
Deal found 8/23![Delta logo]()
$381
One-way flights from Chicago to Key WestSearch for one-way flight options from Chicago to Key West. Find affordable one-way fares based on user searches. Data last updated August 28, 2026.
Search for one-way flight options from Chicago to Key West. Find affordable one-way fares based on user searches. Data last updated August 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/267:28 pm -
1 stop20h 03m
Deal found 8/25![Multiple Airlines logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/297:11 am -
2 stops25h 13m
Deal found 8/26![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/227:11 am -
2 stops25h 13m
Deal found 8/26![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/108:46 am -
1 stop24h 33m
Deal found 8/26![Multiple Airlines logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/248:46 am -
1 stop24h 33m
Deal found 8/27![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/511:45 am -
2 stops22h 40m
Deal found 8/27![Multiple Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/68:00 am -
2 stops24h 24m
Deal found 8/23![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:20 am -
2 stops28h 01m
Deal found 8/26![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/243:50 pm -
1 stop17h 29m
Deal found 8/26![Multiple Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/226:25 am -
2 stops25h 59m
Deal found 8/26![Multiple Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/186:25 am -
2 stops25h 59m
Deal found 8/27![Multiple Airlines logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:25 am -
2 stops27h 56m
Deal found 8/27![Multiple Airlines logo]()
$164
Find flight deals from Chicago to Key West
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Key West (EYW). 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 August 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $276 (Kiwi.com) |
One-way from | $125 (Kiwi.com) |
Popular in | March |
Cheapest in | June |
Average price | $387 |
Good round-trip deal | $339 or less |
Good one-way deal | $238 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Key West 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 August 28, 2026.
Use the filters below to find and compare flights from Chicago to Key West that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoKey West
ORD Chicago O'Hare Intl - EYW Key West
ORDEYW
Chicago O'Hare Intl
Mon 11/30
6:49 am-12:59 pm
1 stop5h 10m
Key West
Wed 12/9
6:06 pm-11:52 pm
1 stop6h 46m
$359
ChicagoKey West
ORD Chicago O'Hare Intl - EYW Key West
ORDEYW
Chicago O'Hare Intl
Fri 12/4
9:56 am-5:11 pm
1 stop6h 15m
Key West
Wed 12/9
6:06 pm-10:59 am
2 stops17h 53m
$434
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Thu 12/3
1:02 pm-8:02 pm
1 stop6h 00m
Key West
Tue 12/8
7:25 am-12:05 pm
1 stop5h 40m
$478
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Mon 12/7
11:28 am-5:11 pm
1 stop4h 43m
Key West
Sat 12/12
6:06 pm-10:55 pm
1 stop5h 49m
$479
ChicagoKey West
ORD Chicago O'Hare Intl - EYW Key West
ORDEYW
Chicago O'Hare Intl
Tue 10/6
6:00 am-1:29 pm
1 stop6h 29m
Key West
Sat 10/10
4:00 pm-5:27 pm
Nonstop2h 27m
$517
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Sat 10/3
11:35 am-8:00 pm
1 stop7h 25m
Key West
Tue 10/6
6:10 pm-10:33 pm
1 stop5h 23m
$568
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Wed 9/16
6:05 am-12:53 pm
1 stop5h 48m
Key West
Tue 9/22
6:19 pm-10:44 pm
1 stop5h 25m
$574
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Mon 11/9
11:27 am-5:10 pm
1 stop4h 43m
Key West
Thu 11/12
7:25 am-11:59 am
1 stop5h 34m
$617
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Fri 1/1
6:00 am-2:01 pm
1 stop7h 01m
Key West
Wed 1/6
6:00 pm-10:10 pm
1 stop5h 10m
$671
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Sat 1/2
9:58 am-5:24 pm
1 stop6h 26m
Key West
Wed 1/6
11:45 am-4:25 pm
1 stop5h 40m
$684
Showing 1-10 of 45 resultsSorted by cheapest first
Compare providers for flights from Chicago to Key West
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 Chicago to Key West in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Key West flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Key West flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Key West flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Key West 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 Chicago-Key West 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 Chicago to Key West
Have a flexible travel schedule? Discover the best time to fly to Key West from Chicago with our price prediction graph.
CHI-EYW
ORD-EYW
MDW-EYW
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 West
CHI-EYW
ORD-EYW
MDW-EYW
What is the cheapest month to book a flight from Chicago to Key West?
Currently, August is the cheapest month in which you can book a flight from Chicago to Key West (average of $368). Flying from Chicago to Key West in March is currently the most expensive (average of $519). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to EYW?
Find hourly flight availability from Chicago to Key West. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 28, 2026.
When flying from Chicago to Key West, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How much does it cost to fly round-trip from Chicago to Key West?
Airfare is below average for this route at the moment.
Chicago to Key West flights typically cost between $358 and $498 in October.The cheapest round-trip price found within the last 5 days was $276 on Multiple Airlines (Oct 1-Oct 5).
How far ahead should I book a flight from Chicago to Key West?
The best time to book flights from Chicago to Key West is 85 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
The best insider tips for Chicago to Key West 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 Chicago to Key West trip
Our travel experts
Reviews of airlines servicing Key West
Get insights into the airlines that provide service to Key West. 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 West. Reviews last updated August 28, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andAmerican Airlines from Chicago to Key West to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.8
Boarding
8.1
Entertainment
7.8
Overall
7.8
Crew
8.5
Food
7.2
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Comfort
7.8
Boarding
8.1
Entertainment
7.8
Overall
7.8
Crew
8.5
Food
7.2
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Comfort
7.8
Boarding
8.1
Entertainment
7.8
Overall
7.8
Crew
8.5
Food
7.2
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Comfort
7.8
Boarding
8.1
Entertainment
7.8
Overall
7.8
Crew
8.5
Food
7.2
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Related info for your journey
Find useful and relevant information for your journey from Chicago to Key West. 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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Other flights to Key West
Explore flights to Key West departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 28, 2026.
Chicago and Key West flights
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Popular flight searches
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Top 3 airlines flying from Chicago to Key West
Discover the top 3 airlines that operate flights from Chicago to Key West. 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 August 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$206 | Average$462 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$249 | Average$410 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$304 | Average$471 | FlexibilityNo cancel fee | On-time71% |