$115+ Cheap flights from O'Hare Intl (ORD) to Key West (EYW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Nov 9 — Nov 161
Round-trip
1 adult, Economy
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Find cheap flights from O'Hare Intl to Key West with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago O'Hare Intl to Key West are usually found in August or July, booked 86 days in advance, depart on a Tuesday or Saturday and return on a Wednesday
Cheap flight deals from O'Hare Intl to Key West
Cheapest
Best
Last-minute
One-way
Cheapest flights from O'Hare Intl to Key WestExplore the most affordable flight options available from O'Hare Intl to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 10, 2026.
Explore the most affordable flight options available from O'Hare Intl to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 12/75:24 pm -
1 stop15h 55m
Tue 12/1510:59 am -
1 stop15h 02m
Deal found 10/7![Multiple Airlines logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 12/125:35 am -
1 stop27h 44m
Tue 12/1510:59 am -
1 stop15h 02m
Deal found 10/9![Multiple Airlines logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/176:30 am -
2 stops25h 54m
Tue 11/2410:04 am -
1 stop15h 39m
Deal found 10/8![Multiple Airlines logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:32 pm -
2 stops19h 18m
Fri 12/1110:59 am -
1 stop23h 19m
Deal found 10/8![Multiple Airlines logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/166:30 am -
2 stops29h 06m
Sat 11/2110:04 am -
1 stop15h 39m
Deal found 10/8![Multiple Airlines logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/176:30 am -
2 stops25h 54m
Mon 11/2312:59 pm -
1 stop12h 44m
Deal found 10/8![Multiple Airlines logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 12/1110:37 pm -
2 stops10h 27m
Tue 12/1510:59 am -
1 stop15h 02m
Deal found 10/9![Multiple Airlines logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 12/125:24 pm -
1 stop15h 55m
Wed 12/1610:45 am -
2 stops27h 05m
Deal found 10/8![Multiple Airlines logo]()
$270
Best flights from O'Hare Intl to Key WestDiscover carefully curated flight deals from O'Hare Intl to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 10, 2026.
Discover carefully curated flight deals from O'Hare Intl to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 10, 2026.
This Delta deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2111:10 am -
1 stop7h 33m
Wed 1/276:00 pm -
1 stop5h 20m
Deal found 10/5![Delta logo]()
$313
This United Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 10/2411:00 am -
Nonstop3h 24m
Sat 10/312:50 pm -
1 stop7h 40m
Deal found 10/8![United Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2111:10 am -
1 stop7h 33m
Tue 1/2611:45 am -
1 stop5h 52m
Deal found 10/8![Delta logo]()
$406
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 12/1812:25 pm -
Nonstop3h 46m
Fri 12/251:35 pm -
1 stop6h 15m
Deal found 10/5![United Airlines logo]()
$439
This United Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 12/1110:55 am -
Nonstop3h 31m
Mon 12/1412:05 pm -
Nonstop3h 50m
Deal found 10/9![United Airlines logo]()
$445
This United Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/127:00 am -
Nonstop3h 24m
Tue 12/154:10 pm -
Nonstop3h 50m
Deal found 10/9![United Airlines logo]()
$502
This United Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/75:55 am -
1 stop7h 18m
Mon 1/115:54 pm -
Nonstop3h 46m
Deal found 10/9![United Airlines logo]()
$515
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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 1/237:31 am -
Nonstop3h 45m
Mon 1/255:54 pm -
Nonstop3h 46m
Deal found 10/6![United Airlines logo]()
$628
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/47:31 am -
Nonstop3h 45m
Fri 2/125:10 pm -
Nonstop3h 55m
Deal found 10/5![United Airlines logo]()
$718
This United Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/199:26 pm -
2 stops15h 57m
Sat 12/264:52 pm -
1 stop7h 32m
Deal found 10/9![United Airlines logo]()
$746
This United Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/317:00 am -
Nonstop3h 41m
Mon 1/44:04 pm -
Nonstop3h 49m
Deal found 10/9![United Airlines logo]()
$756
Last-minute flights from O'Hare Intl to Key WestDiscover last-minute flight deals from O'Hare Intl to Key West. Data last updated October 10, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Key West. Data last updated October 10, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 10/156:58 pm -
1 stop11h 46m
Mon 10/192:54 pm -
1 stop17h 57m
Deal found 10/7![Multiple Airlines logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 10/3010:26 am -
2 stops21h 58m
Sun 11/110:59 am -
1 stop22h 47m
Deal found 10/9![Multiple Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:50 pm -
2 stops36h 34m
Thu 11/1210:59 am -
1 stop22h 47m
Deal found 10/8![Multiple Airlines logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/74:00 pm -
1 stop17h 19m
Sat 11/1410:04 am -
2 stops9h 26m
Deal found 10/8![Multiple Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/149:51 am -
1 stop23h 28m
Wed 11/1810:04 am -
2 stops9h 26m
Deal found 10/6![Multiple Airlines logo]()
$280
This American Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 11/148:15 am -
1 stop7h 12m
Wed 11/186:25 pm -
Nonstop3h 55m
Deal found 10/7![American Airlines logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/166:30 am -
2 stops29h 06m
Sat 11/2110:04 am -
1 stop15h 39m
Deal found 10/8![Multiple Airlines logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/176:30 am -
2 stops25h 54m
Tue 11/2410:04 am -
1 stop15h 39m
Deal found 10/8![Multiple Airlines logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/176:30 am -
2 stops25h 54m
Mon 11/2312:59 pm -
1 stop12h 44m
Deal found 10/8![Multiple Airlines logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/188:59 am -
2 stops24h 20m
Mon 11/2312:59 pm -
1 stop12h 44m
Deal found 10/8![Multiple Airlines logo]()
$292
One-way flights from O'Hare Intl to Key WestSearch for one-way flight options from O'Hare Intl to Key West. Find affordable one-way fares based on user searches. Data last updated October 10, 2026.
Search for one-way flight options from O'Hare Intl to Key West. Find affordable one-way fares based on user searches. Data last updated October 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:35 pm -
2 stops35h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/67:49 pm -
2 stops37h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 11/117:35 pm -
2 stops35h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 12/78:15 am -
2 stops25h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 1/95:16 pm -
1 stop16h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 1/116:00 am -
2 stops27h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 11/97:50 pm -
2 stops39h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:35 pm -
2 stops35h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 12/109:34 pm -
2 stops43h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$130
Find flight deals from O'Hare Intl to Key West
Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Key West (EYW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $173 (Kiwi.com) |
One-way from | $115 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $383 |
Good round-trip deal | $407 or less |
Good one-way deal | $308 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl to Key West that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 10, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Key West that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoKey West
ORD Chicago O'Hare Intl - EYW Key West
ORDEYW
Chicago O'Hare Intl
Thu 4/8
7:10 am-1:08 pm
1 stop4h 58m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$298
Quickest round-trip
ChicagoKey West
ORD Chicago O'Hare Intl - EYW Key West
ORDEYW
Chicago O'Hare Intl
Mon 11/2
11:00 am-3:29 pm
Nonstop3h 29m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$309
ChicagoKey West
ORD Chicago O'Hare Intl - EYW Key West
ORDEYW
Chicago O'Hare Intl
Mon 11/9
11:00 am-3:29 pm
Nonstop3h 29m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$309
ChicagoKey West
ORD Chicago O'Hare Intl - EYW Key West
ORDEYW
Chicago O'Hare Intl
Tue 11/3
11:00 am-3:29 pm
Nonstop3h 29m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$309
ChicagoKey West
ORD Chicago O'Hare Intl - EYW Key West
ORDEYW
Chicago O'Hare Intl
Tue 11/10
11:00 am-3:29 pm
Nonstop3h 29m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$309
ChicagoKey West
ORD Chicago O'Hare Intl - EYW Key West
ORDEYW
Chicago O'Hare Intl
Thu 1/21
11:10 am-7:43 pm
1 stop7h 33m
Key West
Wed 1/27
6:00 pm-10:20 pm
1 stop5h 20m
$313
ChicagoKey West
ORD Chicago O'Hare Intl - EYW Key West
ORDEYW
Chicago O'Hare Intl
Mon 11/2
10:35 am-5:15 pm
1 stop5h 40m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$319
ChicagoKey West
ORD Chicago O'Hare Intl - EYW Key West
ORDEYW
Chicago O'Hare Intl
Mon 1/11
7:10 am-1:08 pm
1 stop4h 58m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$319
ChicagoKey West
ORD Chicago O'Hare Intl - EYW Key West
ORDEYW
Chicago O'Hare Intl
Tue 12/8
10:36 am-5:10 pm
1 stop5h 34m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$319
ChicagoKey West
ORD Chicago O'Hare Intl - EYW Key West
ORDEYW
Chicago O'Hare Intl
Tue 11/10
6:49 am-12:59 pm
1 stop5h 10m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$319
Showing 1-10 of 21 resultsSorted by cheapest first
Compare providers for flights from O'Hare Intl to Key West
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from O'Hare Intl to Key West in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Key West flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago O'Hare Intl Airport-Key West flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Key West flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Key West flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago O'Hare Intl Airport-Key West flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from O'Hare Intl to Key West
Have a flexible travel schedule? Discover the best time to fly to Key West from O'Hare Intl with our price prediction graph.
ORD-EYW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago O'Hare Intl Airport to Key West
How far ahead should I book a flight from Chicago O'Hare Intl Airport to Key West?
The price you pay for your flight from Chicago O'Hare Intl Airport to Key West may vary depending on when you book. For the best chance of a lower fare, look to book 85 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Key West?
Currently, August is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Key West (average of $329). Flying from Chicago O'Hare Intl Airport to Key West in March is currently the most expensive (average of $518). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from ORD to EYW?
Find hourly flight availability from O'Hare Intl to Key West. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 10, 2026.
When flying from Chicago O'Hare Intl Airport to Key West, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
The best insider tips for Chicago O'Hare Intl Airport to Key West flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago O'Hare Intl Airport to Key West trip
Our travel experts
Reviews of airlines servicing Key West
Get insights into the airlines that provide service to Key West. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Key West. Reviews last updated October 10, 2026.
Read reviews from past customers who have flown United Airlines and American Airlines from Chicago O'Hare Intl Airport to Key West. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.3
Overall
7.4
Boarding
7.7
Food
6.7
Entertainment
7.1
Crew
8.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Comfort
7.3
Overall
7.4
Boarding
7.7
Food
6.7
Entertainment
7.1
Crew
8.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Comfort
7.3
Overall
7.4
Boarding
7.7
Food
6.7
Entertainment
7.1
Crew
8.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
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Top 3 airlines flying from O'Hare Intl to Key West
Discover the top 3 airlines that operate flights from O'Hare Intl to Key West. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$196 | Average$368 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$249 | Average$414 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$305 | Average$471 | FlexibilityNo cancel fee | On-time71% |