$144+ 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
Jul 15 — Jul 221
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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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 June 15, 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 June 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/141:14 pm
EYW
- MDW
2 stops9h 49m
Multiple Airlines
Thu 7/162:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$297
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/94:11 pm
EYW
- ORD
Nonstop3h 48m
American Airlines
Sun 7/1211:30 am
ORD
- EYW
Nonstop3h 21m
American Airlines
Deal found 6/15![American Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/911:04 am
EYW
- MDW
2 stops11h 59m
Multiple Airlines
Sun 7/122:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$316
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/117:33 pm
EYW
- ORD
1 stop5h 28m
American Airlines
Tue 7/1411:22 am
ORD
- EYW
Nonstop3h 21m
American Airlines
Deal found 6/10![American Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/67:33 pm
EYW
- ORD
1 stop5h 28m
American Airlines
Tue 7/1411:22 am
ORD
- EYW
Nonstop3h 21m
American Airlines
Deal found 6/14![American Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/911:04 am
EYW
- MDW
2 stops11h 59m
Multiple Airlines
Thu 7/162:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/41:14 pm
EYW
- ORD
2 stops27h 46m
Multiple Airlines
Wed 8/125:13 pm
ORD
- EYW
1 stop17h 12m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$327
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/24:11 pm
EYW
- ORD
Nonstop3h 48m
American Airlines
Wed 7/811:20 am
ORD
- EYW
Nonstop3h 21m
American Airlines
Deal found 6/15![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 6/232:26 pm
EYW
- ORD
1 stop7h 34m
United Airlines
Thu 7/2310:55 am
ORD
- EYW
Nonstop3h 24m
United Airlines
Deal found 6/10![United Airlines logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/189:16 pm
EYW
- RFD
1 stop22h 47m
Allegiant Air
Sat 6/2010:07 am
RFD
- EYW
1 stop26h 39m
Allegiant Air
Deal found 6/13![Allegiant Air logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/272:48 pm
EYW
- MDW
2 stops21h 24m
Multiple Airlines
Sun 7/52:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$430
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 6/193:25 pm
EYW
- RFD
1 stop18h 52m
Allegiant Air
Mon 6/228:35 am
RFD
- EYW
1 stop6h 10m
Allegiant Air
Deal found 6/10![Allegiant Air logo]()
$436
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 June 15, 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 June 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/141:14 pm
EYW
- MDW
2 stops9h 49m
Multiple Airlines
Thu 7/162:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$297
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/294:00 pm
EYW
- ORD
Nonstop3h 55m
United Airlines
Fri 8/710:55 am
ORD
- EYW
Nonstop3h 24m
United Airlines
Deal found 6/10![United Airlines logo]()
$309
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/294:11 pm
EYW
- ORD
Nonstop3h 48m
American Airlines
Fri 8/75:05 am
ORD
- EYW
1 stop6h 50m
American Airlines
Deal found 6/10![American Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:18 pm
EYW
- ORD
1 stop6h 35m
Delta
Thu 7/165:30 am
ORD
- EYW
1 stop6h 53m
Delta
Deal found 6/15![Delta logo]()
$587
This American Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/117:33 pm
EYW
- ORD
1 stop5h 28m
American Airlines
Tue 7/1411:22 am
ORD
- EYW
Nonstop3h 21m
American Airlines
Deal found 6/12![American Airlines logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/911:04 am
EYW
- MDW
2 stops11h 59m
Multiple Airlines
Thu 7/162:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$323
This American Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/41:01 pm
EYW
- ORD
1 stop5h 38m
American Airlines
Wed 8/126:00 am
ORD
- EYW
1 stop6h 08m
American Airlines
Deal found 6/13![American Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/272:48 pm
EYW
- MDW
2 stops21h 24m
Multiple Airlines
Sun 7/52:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$430
This American Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/94:11 pm
EYW
- ORD
Nonstop3h 48m
American Airlines
Thu 7/1611:17 am
ORD
- EYW
Nonstop3h 21m
American Airlines
Deal found 6/11![American Airlines logo]()
$428
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/911:56 am
EYW
- MDW
1 stop5h 19m
Delta
Thu 7/1612:41 pm
MDW
- EYW
1 stop6h 10m
Delta
Deal found 6/11![Delta logo]()
$611
This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/282:26 pm
EYW
- ORD
2 stops18h 10m
United Airlines
Wed 8/56:00 am
ORD
- EYW
1 stop6h 30m
United Airlines
Deal found 6/11![United Airlines logo]()
$613
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/66:24 pm
EYW
- MDW
1 stop4h 53m
Delta
Tue 7/1411:05 am
MDW
- EYW
1 stop7h 46m
Delta
Deal found 6/14![Delta logo]()
$619
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/144:00 pm
EYW
- ORD
Nonstop3h 55m
United Airlines
Thu 7/1610:55 am
ORD
- EYW
Nonstop3h 24m
United Airlines
Deal found 6/15![United Airlines logo]()
$656
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/274:00 pm
EYW
- MDW
1 stop7h 17m
Delta
Sun 7/56:00 am
MDW
- EYW
1 stop6h 43m
Delta
Deal found 6/14![Delta logo]()
$634
This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/112:26 pm
EYW
- ORD
1 stop7h 34m
United Airlines
Tue 7/141:55 pm
ORD
- EYW
2 stops22h 35m
United Airlines
Deal found 6/11![United Airlines logo]()
$691
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 11/276:00 pm
EYW
- MDW
1 stop5h 10m
Delta
Sat 12/510:35 am
MDW
- EYW
1 stop5h 36m
Delta
Deal found 6/10![Delta logo]()
$684
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/274:00 pm
EYW
- MDW
1 stop7h 17m
Delta
Sat 7/116:00 am
MDW
- EYW
1 stop5h 09m
Delta
Deal found 6/14![Delta logo]()
$696
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/911:56 am
EYW
- MDW
1 stop5h 19m
Delta
Sun 7/1211:05 am
MDW
- EYW
1 stop5h 18m
Delta
Deal found 6/15![Delta logo]()
$756
Last-minute flights from Key West to ChicagoDiscover last-minute flight deals from Key West to Chicago. Data last updated June 15, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to Chicago. Data last updated June 15, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/189:16 pm
EYW
- RFD
1 stop22h 47m
Allegiant Air
Sat 6/2010:07 am
RFD
- EYW
1 stop26h 39m
Allegiant Air
Deal found 6/13![Allegiant Air logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 6/189:16 pm
EYW
- RFD
1 stop22h 47m
Allegiant Air
Mon 6/228:35 am
RFD
- EYW
1 stop6h 10m
Allegiant Air
Deal found 6/10![Allegiant Air logo]()
$470
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 6/193:25 pm
EYW
- RFD
1 stop18h 52m
Allegiant Air
Mon 6/228:35 am
RFD
- EYW
1 stop6h 10m
Allegiant Air
Deal found 6/10![Allegiant Air logo]()
$436
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 6/232:26 pm
EYW
- ORD
1 stop7h 34m
United Airlines
Thu 7/2310:55 am
ORD
- EYW
Nonstop3h 24m
United Airlines
Deal found 6/10![United Airlines logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/272:48 pm
EYW
- MDW
2 stops21h 24m
Multiple Airlines
Sun 7/52:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$430
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/24:11 pm
EYW
- ORD
Nonstop3h 48m
American Airlines
Wed 7/811:20 am
ORD
- EYW
Nonstop3h 21m
American Airlines
Deal found 6/15![American Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/67:33 pm
EYW
- ORD
1 stop5h 28m
American Airlines
Tue 7/1411:22 am
ORD
- EYW
Nonstop3h 21m
American Airlines
Deal found 6/14![American Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/94:11 pm
EYW
- ORD
Nonstop3h 48m
American Airlines
Sun 7/1211:30 am
ORD
- EYW
Nonstop3h 21m
American Airlines
Deal found 6/15![American Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/911:04 am
EYW
- MDW
2 stops11h 59m
Multiple Airlines
Sun 7/122:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/911:04 am
EYW
- MDW
2 stops11h 59m
Multiple Airlines
Thu 7/162:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$323
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/117:33 pm
EYW
- ORD
1 stop5h 28m
American Airlines
Tue 7/1411:22 am
ORD
- EYW
Nonstop3h 21m
American Airlines
Deal found 6/10![American Airlines logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/141:14 pm
EYW
- MDW
2 stops9h 49m
Multiple Airlines
Thu 7/162:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$297
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 June 15, 2026.
Search for one-way flight options from Key West to Chicago. Find affordable one-way fares based on user searches. Data last updated June 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 9/910:04 am
EYW
- ORD
2 stops10h 40m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/41:14 pm
EYW
- ORD
2 stops31h 39m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/612:05 pm
EYW
- ORD
1 stop12h 05m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 stop13h 56m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/910:20 pm
EYW
- ORD
1 stop15h 56m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 8/511:46 am
EYW
- ORD
2 stops9h 07m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/111:14 pm
EYW
- ORD
2 stops27h 46m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1210:04 am
EYW
- ORD
2 stops10h 40m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/71:14 pm
EYW
- ORD
2 stops19h 39m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/231:14 pm
EYW
- RFD
1 stop27h 38m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/94:16 pm
EYW
- MDW
2 stops30h 42m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/201:16 pm
EYW
- MDW
2 stops33h 42m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$219
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 June 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $309 (American Airlines) |
One-way from | $144 (Kiwi.com) |
Good round-trip deal | $375 or less |
Good one-way deal | $323 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 June 15, 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 - MDW
EYWMDW
Key West
Tue 7/14
1:14 pm-10:03 pm
2 stops9h 49m
Chicago Midway
Thu 7/16
2:48 pm-9:41 am
1 stop17h 53m
$297
Key WestChicago
EYW - ORD
EYWORD
Key West
Wed 7/29
4:00 pm-6:55 pm
Nonstop3h 55m
Chicago O'Hare Intl
Fri 8/7
10:55 am-3:19 pm
Nonstop3h 24m
$309
Key WestChicago
EYW - ORD
EYWORD
Key West
Wed 7/29
4:11 pm-6:59 pm
Nonstop3h 48m
Chicago O'Hare Intl
Fri 8/7
5:05 am-12:55 pm
1 stop6h 50m
$319
Key WestChicago
EYW - ORD
EYWORD
Key West
Sat 7/11
7:33 pm-12:01 am
1 stop5h 28m
Chicago O'Hare Intl
Tue 7/14
11:22 am-3:43 pm
Nonstop3h 21m
$319
Key WestChicago
EYW - MDW
EYWMDW
Key West
Thu 7/9
11:04 am-10:03 pm
2 stops11h 59m
Chicago Midway
Thu 7/16
2:48 pm-9:41 am
1 stop17h 53m
$323
Key WestChicago
EYW - ORD
EYWORD
Key West
Tue 8/4
1:01 pm-5:39 pm
1 stop5h 38m
Chicago O'Hare Intl
Wed 8/12
6:00 am-1:08 pm
1 stop6h 08m
$329
Quickest round-trip
Key WestChicago
EYW - ORD
EYWORD
Key West
Thu 7/9
4:11 pm-6:59 pm
Nonstop3h 48m
Chicago O'Hare Intl
Thu 7/16
11:17 am-3:38 pm
Nonstop3h 21m
$428
Key WestChicago
EYW - MDW
EYWMDW
Key West
Sat 6/27
2:48 pm-11:12 am
2 stops21h 24m
Chicago Midway
Sun 7/5
2:48 pm-9:41 am
1 stop17h 53m
$430
Key WestChicago
EYW - ORD
EYWORD
Key West
Tue 7/14
6:18 pm-11:53 pm
1 stop6h 35m
Chicago O'Hare Intl
Thu 7/16
5:30 am-1:23 pm
1 stop6h 53m
$587
Key WestChicago
EYW - MDW
EYWMDW
Key West
Thu 7/9
11:56 am-4:15 pm
1 stop5h 19m
Chicago Midway
Thu 7/16
12:41 pm-7:51 pm
1 stop6h 10m
$611
Showing 1-10 of 35 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 June.
| 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-MDW
EYW-ORD
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-MDW
EYW-ORD
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 June 15, 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 June 15, 2026.
The most flights from EYW to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Tuesday, 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 June 15, 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.
Overall
7.1
Boarding
7.5
Crew
7.9
Entertainment
6.8
Comfort
7.2
Food
6.4
Reviews
1 / 20
2.0
MediocreAnonymous,Aug 2025
BNA - ORD
Overall
7.1
Boarding
7.5
Crew
7.9
Entertainment
6.8
Comfort
7.2
Food
6.4
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
Hammond
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 June 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$344 | Average$460 | FlexibilityNo cancel fee | On-time71% |