$114+ Cheap flights from Chicago (CHI) to Key West (EYW)
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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EYW
Nov 1 — Nov 81
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 43 days in advance, depart on a Tuesday or Saturday and return on a Wednesday
Cheap flight deals from Chicago to Key West
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Best
Last-minute
One-way
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 October 2, 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 October 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/306:16 am -
2 stops26h 08m
Fri 11/610:14 am -
1 stop10h 05m
Deal found 9/30![Multiple Airlines logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 11/96:08 am -
2 stops29h 28m
Fri 11/1310:14 am -
1 stop5h 12m
Deal found 10/1![Multiple Airlines logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 11/187:28 pm -
2 stops13h 51m
Mon 11/2312:59 pm -
1 stop12h 44m
Deal found 9/29![Multiple Airlines logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 11/147:15 am -
2 stops24h 49m
Fri 11/204:06 pm -
1 stop9h 37m
Deal found 9/29![Multiple Airlines logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 12/17:32 pm -
2 stops19h 18m
Fri 12/412:59 pm -
1 stop10h 12m
Deal found 9/30![Multiple Airlines logo]()
$291
This American Airlines deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/212:10 pm -
Nonstop3h 22m
Wed 11/116:25 pm -
Nonstop3h 55m
Deal found 10/2![American Airlines logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 11/147:15 am -
2 stops26h 04m
Sat 11/2110:04 am -
1 stop15h 39m
Deal found 9/28![Multiple Airlines logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 10/302:26 pm -
2 stops17h 36m
Fri 11/610:14 am -
1 stop10h 05m
Deal found 10/1![Allegiant Air logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 12/178:41 pm -
1 stop14h 38m
Tue 12/2212:01 pm -
1 stop22h 47m
Deal found 9/29![Multiple Airlines logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/287:28 pm -
2 stops13h 51m
Sun 11/110:59 am -
1 stop22h 47m
Deal found 9/29![Multiple Airlines logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 12/168:15 am -
2 stops26h 06m
Mon 12/2112:59 pm -
1 stop21h 49m
Deal found 9/29![Multiple Airlines logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 12/212:28 pm -
2 stops21h 52m
Sun 12/610:59 am -
1 stop10h 43m
Deal found 9/30![Multiple Airlines logo]()
$356
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 October 2, 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 October 2, 2026.
This Delta deal was found by Cheapflights users on 9/27. 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 12/511:28 am -
1 stop7h 33m
Thu 12/106:06 pm -
1 stop5h 48m
Deal found 9/27![Delta logo]()
$379
This United Airlines deal was found by Cheapflights users on 9/27. 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.
Tue 12/297:00 am -
Nonstop3h 41m
Thu 1/73:04 pm -
1 stop8h 11m
Deal found 9/27![United Airlines logo]()
$557
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/2712:49 pm -
1 stop6h 12m
Tue 11/34:00 pm -
1 stop7h 33m
Deal found 9/30![Delta logo]()
$406
This Delta deal was found by Cheapflights users on 9/27. 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.
Sun 12/135:30 am -
1 stop6h 41m
Sat 12/266:20 pm -
1 stop6h 39m
Deal found 9/27![Delta logo]()
$406
This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 stop6h 55m
Wed 1/66:00 pm -
1 stop5h 10m
Deal found 9/29![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 12/811:28 am -
1 stop7h 33m
Sat 12/126:06 pm -
1 stop5h 48m
Deal found 9/28![Delta logo]()
$439
This United Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 3/12:20 pm -
2 stops23h 05m
Wed 3/316:20 pm -
1 stop5h 55m
Deal found 10/1![United Airlines logo]()
$636
This Delta deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 3/16:00 am -
1 stop6h 08m
Wed 3/316:00 pm -
1 stop5h 10m
Deal found 10/1![Delta logo]()
$466
This United Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/2711:00 am -
Nonstop3h 29m
Sat 10/312:50 pm -
1 stop7h 40m
Deal found 9/28![United Airlines logo]()
$638
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 12/101:02 pm -
1 stop5h 59m
Sat 12/126:06 pm -
1 stop5h 48m
Deal found 9/28![Delta logo]()
$469
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 12/119:59 am -
1 stop6h 11m
Sat 12/126:06 pm -
1 stop6h 50m
Deal found 9/28![Delta logo]()
$469
This United Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 1/610:25 am -
Nonstop3h 47m
Sun 1/105:51 pm -
Nonstop3h 49m
Deal found 10/1![United Airlines logo]()
$694
This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/295:27 am -
1 stop6h 26m
Mon 11/22:00 pm -
1 stop7h 38m
Deal found 9/29![Delta logo]()
$469
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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.
Sun 10/186:00 am -
1 stop6h 29m
Sat 10/244:20 pm -
Nonstop3h 39m
Deal found 9/29![United Airlines logo]()
$697
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 stop6h 55m
Sat 1/96:00 pm -
1 stop5h 10m
Deal found 9/28![Delta logo]()
$517
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 1/76:00 am -
1 stop6h 08m
Thu 1/146:00 pm -
1 stop5h 10m
Deal found 9/28![Delta logo]()
$614
This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 1/1610:35 am -
1 stop5h 36m
Sat 1/236:00 pm -
1 stop5h 10m
Deal found 9/29![Delta logo]()
$614
This Delta deal was found by Cheapflights users on 9/27. 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.
Tue 12/295:25 am -
1 stop14h 33m
Tue 1/511:45 am -
1 stop7h 47m
Deal found 9/27![Delta logo]()
$614
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 11/91:05 pm -
1 stop5h 55m
Thu 11/127:30 am -
1 stop5h 29m
Deal found 9/28![Delta logo]()
$637
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 1/411:10 am -
1 stop7h 33m
Sun 1/107:00 am -
2 stops10h 37m
Deal found 9/30![Delta logo]()
$729
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 2/2411:10 am -
1 stop7h 33m
Sun 3/77:00 am -
2 stops10h 37m
Deal found 9/28![Delta logo]()
$729
Last-minute flights from Chicago to Key WestDiscover last-minute flight deals from Chicago to Key West. Data last updated October 2, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Key West. Data last updated October 2, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/287:28 pm -
2 stops13h 51m
Sun 11/110:59 am -
1 stop22h 47m
Deal found 9/29![Multiple Airlines logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/299:51 am -
1 stop20h 48m
Tue 11/31:16 pm -
2 stops24h 35m
Deal found 9/30![Multiple Airlines logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/299:51 am -
1 stop20h 48m
Mon 11/29:34 am -
2 stops28h 17m
Deal found 9/30![Multiple Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/306:16 am -
2 stops26h 08m
Fri 11/610:14 am -
1 stop10h 05m
Deal found 9/30![Multiple Airlines logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 10/302:26 pm -
2 stops17h 36m
Fri 11/610:14 am -
1 stop10h 05m
Deal found 10/1![Allegiant Air logo]()
$303
This American Airlines deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/212:10 pm -
Nonstop3h 22m
Wed 11/116:25 pm -
Nonstop3h 55m
Deal found 10/2![American Airlines logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 11/96:08 am -
2 stops29h 28m
Fri 11/1310:14 am -
1 stop5h 12m
Deal found 10/1![Multiple Airlines logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 11/147:15 am -
2 stops24h 49m
Fri 11/204:06 pm -
1 stop9h 37m
Deal found 9/29![Multiple Airlines logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 11/147:15 am -
2 stops26h 04m
Sat 11/2110:04 am -
1 stop15h 39m
Deal found 9/28![Multiple Airlines logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 11/156:08 am -
2 stops27h 11m
Sun 11/2210:59 am -
1 stop9h 48m
Deal found 10/1![Multiple Airlines logo]()
$369
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 11/187:28 pm -
2 stops13h 51m
Mon 11/2312:59 pm -
1 stop12h 44m
Deal found 9/29![Multiple Airlines logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 11/218:42 pm -
1 stop12h 37m
Tue 11/2411:04 am -
1 stop9h 43m
Deal found 10/1![Multiple Airlines logo]()
$365
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 October 2, 2026.
Search for one-way flight options from Chicago to Key West. Find affordable one-way fares based on user searches. Data last updated October 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/277:15 am -
2 stops25h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/317:15 am -
2 stops27h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/246:21 am -
2 stops28h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/287:15 am -
2 stops26h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/247:44 pm -
2 stops13h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/236:15 am -
2 stops26h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 11/47:35 pm -
2 stops37h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Multiple Airlines logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/267:44 pm -
2 stops36h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Multiple Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 12/3111:36 am -
2 stops21h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 11/164:31 pm -
3 stops19h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Multiple Airlines logo]()
$211
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 October 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $245 (Kiwi.com) |
One-way from | $114 (Kiwi.com) |
Popular in | November |
Cheapest in | June |
Average price | $419 |
Good round-trip deal | $402 or less |
Good one-way deal | $308 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 October 2, 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
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Mon 10/26
6:15 am-9:24 am
2 stops50h 09m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$153
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Mon 11/16
6:42 pm-9:24 am
2 stops37h 42m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$153
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Sat 10/24
6:21 am-11:21 am
2 stops28h 00m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$153
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Fri 10/23
6:15 am-9:24 am
3 stops26h 09m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$178
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Thu 12/31
11:36 am-10:19 am
2 stops21h 43m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$203
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Fri 10/9
6:52 am-9:24 am
2 stops25h 32m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$254
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Sat 12/26
8:07 pm-10:19 am
1 stop13h 12m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$306
Quickest round-trip
ChicagoKey West
ORD Chicago O'Hare Intl - EYW Key West
ORDEYW
Chicago O'Hare Intl
Fri 11/27
11:00 am-3:29 pm
Nonstop3h 29m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$309
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Sun 12/27
8:07 pm-11:21 am
3 stops38h 14m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$310
ChicagoKey West
ORD Chicago O'Hare Intl - EYW Key West
ORDEYW
Chicago O'Hare Intl
Wed 3/31
9:30 am-5:11 pm
1 stop6h 41m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$319
Showing 1-10 of 37 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 October.
| 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
MDW-EYW
ORD-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
MDW-EYW
ORD-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 $364). 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 October 2, 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 $349 and $547 in October.The cheapest round-trip price found within the last 5 days was $245 on Multiple Airlines (Oct 30-Nov 6).
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 October 2, 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.
Food
7.2
Comfort
7.8
Crew
8.5
Overall
7.8
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Food
7.2
Comfort
7.8
Crew
8.5
Overall
7.8
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Food
7.2
Comfort
7.8
Crew
8.5
Overall
7.8
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Food
7.2
Comfort
7.8
Crew
8.5
Overall
7.8
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
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 October 2, 2026.
Chicago and Key West flights
Browse other Chicago and Key West flight options. Last updated on October 2, 2026.
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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 October 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$196 | Average$426 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$249 | Average$415 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$304 | Average$471 | FlexibilityNo cancel fee | On-time71% |