$126+ Cheap flights from Key West (EYW) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
Sep 1 — Sep 81
Round-trip
1 adult, Economy
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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
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Key West to Chicago
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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 August 2, 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 August 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 9/312:05 pm
EYW
- ORD
1 stop12h 03m
Multiple Airlines
Mon 9/78:05 am
ORD
- EYW
2 stops27h 29m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
Thu 9/1010:59 am
EYW
- ORD
1 stop24h 21m
Multiple Airlines
Sun 9/1310:26 am
ORD
- EYW
2 stops24h 53m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 8/1. 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.
Thu 10/110:59 am
EYW
- ORD
1 stop13h 00m
Multiple Airlines
Sat 10/314:44 pm
ORD
- EYW
1 stop19h 54m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Mon 8/2412:07 pm
EYW
- ORD
1 stop12h 01m
Multiple Airlines
Sun 8/307:05 am
ORD
- EYW
2 stops52h 29m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 10/310:04 am
EYW
- RFD
2 stops24h 14m
Multiple Airlines
Mon 10/56:31 pm
RFD
- EYW
1 stop17h 05m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$297
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/34:56 pm
EYW
- ORD
Nonstop3h 52m
American Airlines
Mon 9/711:59 am
ORD
- EYW
Nonstop3h 19m
American Airlines
Deal found 7/30![American Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 8/2. 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.
Sat 9/1211:30 am
EYW
- ORD
1 stop7h 37m
American Airlines
Sat 9/198:05 am
ORD
- EYW
1 stop7h 04m
American Airlines
Deal found 8/2![American Airlines logo]()
$323
This American Airlines deal was found by Cheapflights users on 7/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/271:35 pm
EYW
- ORD
1 stop5h 19m
American Airlines
Wed 9/26:00 am
ORD
- EYW
1 stop6h 08m
American Airlines
Deal found 7/28![American Airlines logo]()
$331
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 10/17:40 am
EYW
- MDW
1 stop5h 14m
Delta
Sat 10/311:35 am
MDW
- EYW
1 stop7h 25m
Delta
Deal found 7/31![Delta logo]()
$331
This Delta deal was found by Cheapflights users on 7/28. 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 8/2711:48 am
EYW
- MDW
1 stop5h 27m
Delta
Wed 9/26:05 am
MDW
- EYW
1 stop5h 55m
Delta
Deal found 7/28![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 8/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1211:42 am
EYW
- MDW
1 stop4h 42m
Delta
Sat 9/1911:35 am
MDW
- EYW
1 stop7h 25m
Delta
Deal found 8/2![Delta logo]()
$381
This Delta deal was found by Cheapflights users on 8/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:15 pm
EYW
- MDW
1 stop5h 21m
Delta
Wed 8/126:05 am
MDW
- EYW
1 stop5h 55m
Delta
Deal found 8/2![Delta logo]()
$387
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 August 2, 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 August 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 9/312:05 pm
EYW
- ORD
1 stop12h 03m
Multiple Airlines
Mon 9/78:05 am
ORD
- EYW
2 stops27h 29m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$263
This American Airlines deal was found by Cheapflights users on 7/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/34:56 pm
EYW
- ORD
Nonstop3h 52m
American Airlines
Mon 9/711:59 am
ORD
- EYW
Nonstop3h 19m
American Airlines
Deal found 7/29![American Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 10/17:40 am
EYW
- MDW
1 stop5h 14m
Delta
Sat 10/311:35 am
MDW
- EYW
1 stop7h 25m
Delta
Deal found 7/31![Delta logo]()
$331
This United Airlines deal was found by Cheapflights users on 7/29. 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.
Mon 12/213:50 pm
EYW
- ORD
1 stop8h 47m
United Airlines
Tue 12/299:00 am
ORD
- EYW
Nonstop3h 11m
United Airlines
Deal found 7/29![United Airlines logo]()
$497
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 10/310:04 am
EYW
- RFD
2 stops24h 14m
Multiple Airlines
Mon 10/56:31 pm
RFD
- EYW
1 stop17h 05m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$297
This American Airlines deal was found by Cheapflights users on 7/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/271:35 pm
EYW
- ORD
1 stop5h 19m
American Airlines
Wed 9/26:00 am
ORD
- EYW
1 stop6h 08m
American Airlines
Deal found 7/28![American Airlines logo]()
$331
This Delta deal was found by Cheapflights users on 7/28. 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 8/2711:48 am
EYW
- MDW
1 stop5h 27m
Delta
Wed 9/26:05 am
MDW
- EYW
1 stop5h 55m
Delta
Deal found 7/28![Delta logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
Thu 8/277:53 pm
EYW
- ORD
2 stops25h 06m
Multiple Airlines
Wed 9/27:44 pm
ORD
- EYW
1 stop14h 41m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 8/1. 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.
Sat 10/36:19 pm
EYW
- ORD
1 stop6h 40m
Delta
Mon 10/56:40 am
ORD
- EYW
1 stop5h 13m
Delta
Deal found 8/1![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 8/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1211:42 am
EYW
- MDW
1 stop4h 42m
Delta
Sat 9/1911:35 am
MDW
- EYW
1 stop7h 25m
Delta
Deal found 8/2![Delta logo]()
$381
This Delta deal was found by Cheapflights users on 8/1. 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.
Sat 10/36:19 pm
EYW
- ORD
1 stop6h 40m
Delta
Sun 10/46:40 am
ORD
- EYW
1 stop5h 13m
Delta
Deal found 8/1![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 8/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:19 pm
EYW
- MDW
1 stop5h 25m
Delta
Mon 10/56:05 am
MDW
- EYW
1 stop5h 48m
Delta
Deal found 8/2![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 8/1. 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.
Fri 8/146:15 pm
EYW
- MDW
1 stop5h 21m
Delta
Thu 8/2012:46 pm
MDW
- EYW
1 stop6h 11m
Delta
Deal found 8/1![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 8/1. 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.
Fri 10/166:10 pm
EYW
- MDW
1 stop5h 23m
Delta
Sun 10/1812:45 pm
MDW
- EYW
1 stop6h 16m
Delta
Deal found 8/1![Delta logo]()
$417
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 10/76:10 pm
EYW
- ORD
1 stop6h 42m
Delta
Fri 10/911:21 am
ORD
- EYW
1 stop7h 40m
Delta
Deal found 7/31![Delta logo]()
$460
This Delta deal was found by Cheapflights users on 7/29. 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 9/311:48 am
EYW
- MDW
1 stop5h 27m
Delta
Mon 9/76:05 am
MDW
- EYW
1 stop5h 55m
Delta
Deal found 7/29![Delta logo]()
$569
This Delta deal was found by Cheapflights users on 8/1. 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.
Tue 10/67:40 am
EYW
- MDW
1 stop5h 10m
Delta
Thu 10/812:45 pm
MDW
- EYW
1 stop6h 16m
Delta
Deal found 8/1![Delta logo]()
$597
This Delta deal was found by Cheapflights users on 8/1. 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 11/26:11 pm
EYW
- MDW
1 stop5h 22m
Delta
Wed 11/46:04 am
MDW
- EYW
1 stop7h 16m
Delta
Deal found 8/1![Delta logo]()
$597
This Delta deal was found by Cheapflights users on 7/29. 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.
Mon 12/216:00 pm
EYW
- MDW
1 stop5h 10m
Delta
Tue 12/2910:35 am
MDW
- EYW
1 stop8h 08m
Delta
Deal found 7/29![Delta logo]()
$602
This Delta deal was found by Cheapflights users on 7/29. 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.
Tue 12/226:00 pm
EYW
- MDW
1 stop5h 10m
Delta
Wed 12/3010:35 am
MDW
- EYW
1 stop8h 08m
Delta
Deal found 7/29![Delta logo]()
$638
Last-minute flights from Key West to ChicagoDiscover last-minute flight deals from Key West to Chicago. Data last updated August 2, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to Chicago. Data last updated August 2, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/54:56 pm
EYW
- ORD
Nonstop3h 52m
American Airlines
Wed 8/1211:59 am
ORD
- EYW
Nonstop3h 19m
American Airlines
Deal found 7/30![American Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 8/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:15 pm
EYW
- MDW
1 stop5h 21m
Delta
Wed 8/126:05 am
MDW
- EYW
1 stop5h 55m
Delta
Deal found 8/2![Delta logo]()
$387
This Delta deal was found by Cheapflights users on 8/1. 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.
Fri 8/146:15 pm
EYW
- MDW
1 stop5h 21m
Delta
Thu 8/2012:46 pm
MDW
- EYW
1 stop6h 11m
Delta
Deal found 8/1![Delta logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/1412:07 pm
EYW
- ORD
1 stop12h 03m
Multiple Airlines
Thu 8/208:05 am
ORD
- EYW
2 stops10h 08m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$422
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Mon 8/2412:07 pm
EYW
- ORD
1 stop12h 01m
Multiple Airlines
Sun 8/307:05 am
ORD
- EYW
2 stops52h 29m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$285
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/264:56 pm
EYW
- ORD
Nonstop3h 52m
American Airlines
Mon 8/3111:59 am
ORD
- EYW
Nonstop3h 19m
American Airlines
Deal found 7/30![American Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 7/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/271:35 pm
EYW
- ORD
1 stop5h 19m
American Airlines
Wed 9/26:00 am
ORD
- EYW
1 stop6h 08m
American Airlines
Deal found 7/28![American Airlines logo]()
$331
This Delta deal was found by Cheapflights users on 7/28. 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 8/2711:48 am
EYW
- MDW
1 stop5h 27m
Delta
Wed 9/26:05 am
MDW
- EYW
1 stop5h 55m
Delta
Deal found 7/28![Delta logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
Thu 8/277:53 pm
EYW
- ORD
2 stops25h 06m
Multiple Airlines
Wed 9/27:44 pm
ORD
- EYW
1 stop14h 41m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$344
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 August 2, 2026.
Search for one-way flight options from Key West to Chicago. Find affordable one-way fares based on user searches. Data last updated August 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 8/2611:46 am
EYW
- ORD
2 stops9h 22m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/3010:04 am
EYW
- ORD
2 stops9h 19m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 9/1610:04 am
EYW
- MDW
2 stops8h 47m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 10/2912:01 pm
EYW
- ORD
1 stop28h 25m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/11:14 pm
EYW
- ORD
2 stops31h 54m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 10/212:59 pm
EYW
- ORD
2 stops23h 52m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 10/112:01 pm
EYW
- ORD
2 stops24h 39m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/3112:07 pm
EYW
- ORD
1 stop12h 01m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 10/3110:04 am
EYW
- ORD
2 stops10h 40m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$137
This Delta deal was found by Cheapflights users on 7/30. 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 9/296:19 pm
EYW
- MDW
1 stop5h 25m
Delta
Deal found 7/30![Delta logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/1211:46 am
EYW
- MDW
2 stops11h 17m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 11/162:51 pm
EYW
- MDW
2 stops21h 07m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$181
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 August 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $263 (Kiwi.com) |
One-way from | $126 (Kiwi.com) |
Good round-trip deal | $343 or less |
Good one-way deal | $328 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 2,558,603 searches. Data last updated August 2, 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 - ORD
EYWORD
Key West
Thu 9/3
12:05 pm-11:08 pm
1 stop12h 03m
Chicago O'Hare Intl
Mon 9/7
8:05 am-12:34 pm
2 stops27h 29m
$263
Key WestChicago
EYW - RFD
EYWRFD
Key West
Sat 10/3
10:04 am-9:18 am
2 stops24h 14m
Chicago Greater Rockford
Mon 10/5
6:31 pm-12:36 pm
1 stop17h 05m
$297
Quickest round-trip
Key WestChicago
EYW - ORD
EYWORD
Key West
Thu 9/3
4:56 pm-7:48 pm
Nonstop3h 52m
Chicago O'Hare Intl
Mon 9/7
11:59 am-4:18 pm
Nonstop3h 19m
$319
Key WestChicago
EYW - MDW
EYWMDW
Key West
Thu 10/1
7:40 am-11:54 am
1 stop5h 14m
Chicago Midway
Sat 10/3
11:35 am-8:00 pm
1 stop7h 25m
$331
Key WestChicago
EYW - ORD
EYWORD
Key West
Thu 8/27
1:35 pm-5:54 pm
1 stop5h 19m
Chicago O'Hare Intl
Wed 9/2
6:00 am-1:08 pm
1 stop6h 08m
$331
Key WestChicago
EYW - MDW
EYWMDW
Key West
Thu 8/27
11:48 am-4:15 pm
1 stop5h 27m
Chicago Midway
Wed 9/2
6:05 am-1:00 pm
1 stop5h 55m
$339
Key WestChicago
EYW - ORD
EYWORD
Key West
Thu 8/27
7:53 pm-7:59 pm
2 stops25h 06m
Chicago O'Hare Intl
Wed 9/2
7:44 pm-11:25 am
1 stop14h 41m
$344
Key WestChicago
EYW - ORD
EYWORD
Key West
Sat 10/3
6:19 pm-11:59 pm
1 stop6h 40m
Chicago O'Hare Intl
Mon 10/5
6:40 am-12:53 pm
1 stop5h 13m
$359
Key WestChicago
EYW - MDW
EYWMDW
Key West
Sat 9/12
11:42 am-3:24 pm
1 stop4h 42m
Chicago Midway
Sat 9/19
11:35 am-8:00 pm
1 stop7h 25m
$381
Key WestChicago
EYW - ORD
EYWORD
Key West
Sat 10/3
6:19 pm-11:59 pm
1 stop6h 40m
Chicago O'Hare Intl
Sun 10/4
6:40 am-12:53 pm
1 stop5h 13m
$389
Showing 1-10 of 41 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 August.
| 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
What is the cheapest time of day to fly from EYW to CHI?
Find hourly flight availability from Key West to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 2, 2026.
When flying from Key West to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Key West to Chicago
Explore weekly flight availability from Key West to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 2, 2026.
The most flights from EYW to CHI are scheduled on a Saturday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).
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 August 2, 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.
Entertainment
6.8
Comfort
7.2
Boarding
7.5
Crew
7.9
Food
6.4
Overall
7.1
Reviews
1 / 20
2.0
MediocreAnonymous,Aug 2025
BNA - ORD
Entertainment
6.8
Comfort
7.2
Boarding
7.5
Crew
7.9
Food
6.4
Overall
7.1
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
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Porter
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Key West and Chicago flights
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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 2,558,603 searches. Data last updated August 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$329 | Average$460 | FlexibilityNo cancel fee | On-time71% |