$108+ Cheap flights from Key West (EYW) to O'Hare Intl (ORD)
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 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
Oct 4 — Oct 111
Round-trip
1 adult, Economy
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Find cheap flights from Key West to O'Hare Intl with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Key West to O'Hare Intl
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Best
Last-minute
One-way
Cheapest flights from Key West to O'Hare IntlExplore the most affordable flight options available from Key West to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 4, 2026.
Explore the most affordable flight options available from Key West to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 4, 2026.
This American Airlines deal was found by Cheapflights users on 9/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/101:14 pm -
Nonstop3h 46m
Sun 12/137:30 am -
Nonstop3h 24m
Deal found 9/1![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 8/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/264:00 pm -
Nonstop2h 27m
Mon 9/285:00 am -
1 stop7h 29m
Deal found 8/30![United Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 8/30. 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.
Sat 9/267:47 pm -
1 stop5h 46m
Mon 9/285:00 am -
1 stop7h 17m
Deal found 8/30![American Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 8/31. 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 11/2611:43 am -
1 stop5h 57m
Mon 11/306:49 am -
1 stop5h 10m
Deal found 8/31![Delta logo]()
$379
This American Airlines deal was found by Cheapflights users on 9/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1511:30 am -
1 stop7h 37m
Tue 9/2210:05 am -
1 stop8h 12m
Deal found 9/1![American Airlines logo]()
$389
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 11/2012:59 pm -
1 stop20h 05m
Sun 11/2210:23 am -
1 stop22h 56m
Deal found 8/30![Multiple Airlines logo]()
$397
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 10/1410:04 am -
2 stops9h 27m
Wed 10/218:46 am -
1 stop24h 33m
Deal found 8/30![Multiple Airlines logo]()
$405
This American Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 12/301:23 pm -
1 stop5h 22m
Mon 1/47:20 am -
Nonstop3h 31m
Deal found 9/3![American Airlines logo]()
$415
This American Airlines deal was found by Cheapflights users on 8/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:30 pm -
1 stop8h 01m
Sat 9/198:59 am -
1 stop7h 56m
Deal found 8/31![American Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 8/30. 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 10/148:03 pm -
1 stop5h 35m
Wed 10/218:05 am -
1 stop7h 06m
Deal found 8/30![American Airlines logo]()
$423
Best flights from Key West to O'Hare IntlDiscover carefully curated flight deals from Key West to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 4, 2026.
Discover carefully curated flight deals from Key West to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 4, 2026.
This United Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/34:00 pm -
Nonstop2h 27m
Tue 10/65:00 am -
1 stop7h 29m
Deal found 9/3![United Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/310:21 am -
1 stop6h 09m
Tue 10/68:05 am -
1 stop5h 31m
Deal found 9/3![American Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 8/31. 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 11/2611:43 am -
1 stop5h 57m
Mon 11/306:49 am -
1 stop5h 10m
Deal found 8/31![Delta logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 11/2012:59 pm -
1 stop20h 05m
Sun 11/2210:23 am -
1 stop22h 56m
Deal found 8/30![Multiple Airlines logo]()
$397
This United Airlines deal was found by Cheapflights users on 8/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/264:00 pm -
Nonstop2h 27m
Mon 9/285:00 am -
1 stop7h 29m
Deal found 8/30![United Airlines logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 10/1410:04 am -
2 stops9h 27m
Wed 10/218:46 am -
1 stop24h 33m
Deal found 8/30![Multiple Airlines logo]()
$405
This American Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 12/301:23 pm -
1 stop5h 22m
Mon 1/412:05 pm -
1 stop5h 41m
Deal found 9/3![American Airlines logo]()
$425
This United Airlines deal was found by Cheapflights users on 9/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/244:00 pm -
Nonstop2h 27m
Mon 10/2611:00 am -
Nonstop3h 29m
Deal found 9/2![United Airlines logo]()
$430
This American Airlines deal was found by Cheapflights users on 9/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1511:30 am -
2 stops7h 59m
Tue 9/228:05 am -
1 stop5h 44m
Deal found 9/1![American Airlines logo]()
$450
This United Airlines deal was found by Cheapflights users on 8/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/204:10 pm -
Nonstop3h 50m
Sun 11/225:00 am -
1 stop7h 52m
Deal found 8/30![United Airlines logo]()
$475
This United Airlines deal was found by Cheapflights users on 8/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/282:51 pm -
1 stop8h 27m
Fri 10/3011:00 am -
Nonstop3h 29m
Deal found 8/31![United Airlines logo]()
$607
This United Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/252:15 pm -
1 stop9h 13m
Mon 9/286:00 am -
1 stop6h 29m
Deal found 9/3![United Airlines logo]()
$618
Last-minute flights from Key West to O'Hare IntlDiscover last-minute flight deals from Key West to O'Hare Intl. Data last updated September 4, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to O'Hare Intl. Data last updated September 4, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/2. 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 9/54:56 pm -
Nonstop3h 52m
Tue 9/811:59 am -
Nonstop3h 19m
Deal found 9/2![American Airlines logo]()
$471
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:59 am -
1 stop13h 00m
Thu 9/1710:26 am -
2 stops20h 42m
Deal found 9/4![Multiple Airlines logo]()
$453
This American Airlines deal was found by Cheapflights users on 9/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1511:30 am -
1 stop7h 37m
Tue 9/2210:05 am -
1 stop8h 12m
Deal found 9/1![American Airlines logo]()
$389
This American Airlines deal was found by Cheapflights users on 8/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:30 pm -
1 stop8h 01m
Sat 9/198:59 am -
1 stop7h 56m
Deal found 8/31![American Airlines logo]()
$419
This United Airlines deal was found by Cheapflights users on 8/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/264:00 pm -
Nonstop2h 27m
Mon 9/285:00 am -
1 stop7h 29m
Deal found 8/30![United Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 8/30. 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.
Sat 9/267:47 pm -
1 stop5h 46m
Mon 9/285:00 am -
1 stop7h 17m
Deal found 8/30![American Airlines logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 10/1410:04 am -
2 stops9h 27m
Wed 10/218:46 am -
1 stop24h 33m
Deal found 8/30![Multiple Airlines logo]()
$405
This American Airlines deal was found by Cheapflights users on 8/30. 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 10/148:03 pm -
1 stop5h 35m
Wed 10/218:05 am -
1 stop7h 06m
Deal found 8/30![American Airlines logo]()
$423
This Kiwi.com deal was found by Cheapflights users on 8/31. 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.
Thu 10/1510:59 am -
1 stop21h 32m
Mon 10/197:44 pm -
2 stops36h 40m
Deal found 8/31![Multiple Airlines logo]()
$443
This United Airlines deal was found by Cheapflights users on 9/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/244:00 pm -
Nonstop2h 27m
Mon 10/2611:00 am -
Nonstop3h 29m
Deal found 9/2![United Airlines logo]()
$430
One-way flights from Key West to O'Hare IntlSearch for one-way flight options from Key West to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated September 4, 2026.
Search for one-way flight options from Key West to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated September 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/210:45 am -
1 stop24h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Multiple Airlines logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 12/310:59 am -
1 stop15h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/30![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 -
2 stops9h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/410:04 am -
2 stops9h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Multiple Airlines logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/3012:59 pm -
2 stops30h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/212:59 pm -
2 stops30h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Multiple Airlines logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 -
2 stops9h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Multiple Airlines logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3110:04 am -
2 stops9h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/31:16 pm -
2 stops24h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Multiple Airlines logo]()
$147
Find flight deals from Key West to O'Hare Intl
Discover tips and strategies to find the most affordable flight options for your journey from Key West (EYW) to O'Hare Intl (ORD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $339 (American Airlines) |
One-way from | $108 (Kiwi.com) |
Popular in | January |
Cheapest in | December |
Average price | $456 |
Good round-trip deal | $411 or less |
Good one-way deal | $328 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Key West to O'Hare Intl that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 4, 2026.
Use the filters below to find and compare flights from Key West to Chicago O'Hare Intl Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Thu 10/22
8:36 pm-3:30 pm
3 stops43h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$285
Quickest round-trip
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Tue 3/2
4:05 pm-6:30 pm
Nonstop3h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$299
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Sat 10/3
4:20 pm-6:59 pm
Nonstop3h 39m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$299
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Fri 10/30
4:10 pm-7:00 pm
Nonstop3h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$299
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Tue 9/29
11:42 am-4:37 pm
1 stop5h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$309
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Wed 3/3
6:00 pm-10:20 pm
1 stop5h 20m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$309
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Tue 11/3
7:40 am-2:28 pm
1 stop7h 48m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$309
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Fri 2/26
6:00 pm-11:50 pm
1 stop6h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$309
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Tue 3/2
6:00 pm-10:20 pm
1 stop5h 20m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$309
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Sat 10/3
4:00 pm-5:27 pm
Nonstop2h 27m
Chicago O'Hare Intl
Tue 10/6
5:00 am-1:29 pm
1 stop7h 29m
$349
Showing 1-10 of 21 resultsSorted by cheapest first
Compare providers for flights from Key West to O'Hare Intl
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 O'Hare Intl in September.
| 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 Key West-Chicago O'Hare Intl Airport 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 O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Key West-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Key West-Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl
Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Key West with our price prediction graph.
EYW-ORD
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 O'Hare Intl Airport
The best insider tips for Key West to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport trip
Our travel experts
Reviews of airlines servicing O'Hare Intl
Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated September 4, 2026.
Peruse reviews from past customers who have flown with American Airlines from Key West to Chicago O'Hare Intl Airport 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.
Overall
7.1
Crew
7.9
Food
6.4
Entertainment
6.8
Boarding
7.5
Comfort
7.2
Reviews
1 / 20
2.0
MediocreAnonymous,Aug 2025
BNA - ORD
Overall
7.1
Crew
7.9
Food
6.4
Entertainment
6.8
Boarding
7.5
Comfort
7.2
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 O'Hare Intl. 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 O'Hare Intl Airport?
Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locationsBenton Harbor
Rosemont
Naperville
Glenview
Lake Geneva
Schaumburg
Oakbrook Terrace
Delavan
Oak Brook
Libertyville
Des Plaines
Orland Park
Hoffman Estates
Aurora
Beloit
Rockford
South Holland
Elgin
Racine
Skokie
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Top airline flying from Key West to O'Hare Intl
Discover the top airline that operate flights from Key West to O'Hare Intl. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$319 | Average$409 | FlexibilityNo cancel fee | On-time71% |