$87+ Cheap flights from O'Hare Intl (ORD) to Key West (EYW)
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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Jun 3 — Jun 101
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 July or January, booked 86 days in advance, depart on a Tuesday or Wednesday 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 May 4, 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 May 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/21:29 pm
ORD
- EYW
2 stops20h 37m
Multiple Airlines
Sat 6/62:48 pm
EYW
- ORD
1 stop22h 35m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/68:10 am
ORD
- EYW
1 stop4h 59m
Delta
Mon 6/86:24 pm
EYW
- ORD
1 stop6h 35m
Delta
Deal found 4/29![Delta logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/98:30 am
ORD
- EYW
1 stop24h 54m
Multiple Airlines
Wed 5/1311:46 am
EYW
- ORD
1 stop22h 41m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Thu 5/285:11 pm
ORD
- EYW
1 stop17h 16m
Multiple Airlines
Mon 6/11:11 pm
EYW
- ORD
2 stops31h 18m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/311:46 am
ORD
- EYW
Nonstop3h 27m
American Airlines
Tue 6/94:17 pm
EYW
- ORD
Nonstop3h 48m
American Airlines
Deal found 4/29![American Airlines logo]()
$336
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/131:59 pm
ORD
- EYW
2 stops19h 25m
Multiple Airlines
Fri 5/151:11 pm
EYW
- ORD
1 stop24h 12m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$337
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Fri 5/151:50 pm
ORD
- EYW
Nonstop3h 26m
American Airlines
Thu 5/214:19 pm
EYW
- ORD
Nonstop3h 53m
American Airlines
Deal found 4/30![American Airlines logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/98:30 am
ORD
- EYW
1 stop24h 54m
Multiple Airlines
Tue 5/121:14 pm
EYW
- ORD
1 stop24h 09m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/138:00 pm
ORD
- EYW
2 stops36h 41m
Multiple Airlines
Tue 6/301:14 pm
EYW
- ORD
1 stop7h 25m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$343
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 May 4, 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 May 4, 2026.
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/59:49 am
ORD
- EYW
1 stop6h 34m
Delta
Mon 6/86:24 pm
EYW
- ORD
1 stop6h 35m
Delta
Deal found 5/1![Delta logo]()
$329
This United Airlines deal was found by Cheapflights users on 5/3. 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 7/410:55 am
ORD
- EYW
Nonstop3h 24m
United Airlines
Wed 7/82:26 pm
EYW
- ORD
1 stop7h 34m
United Airlines
Deal found 5/3![United Airlines logo]()
$464
This Delta deal was found by Cheapflights users on 5/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/85:30 am
ORD
- EYW
1 stop6h 58m
Delta
Sat 6/137:50 am
EYW
- ORD
1 stop7h 24m
Delta
Deal found 5/4![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/239:45 am
ORD
- EYW
1 stop6h 38m
Delta
Sun 8/26:18 pm
EYW
- ORD
1 stop6h 35m
Delta
Deal found 5/1![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/301:44 pm
ORD
- EYW
1 stop5h 07m
Delta
Sun 8/211:56 am
EYW
- ORD
1 stop7h 49m
Delta
Deal found 4/29![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Tue 7/2810:43 am
ORD
- EYW
Nonstop3h 24m
United Airlines
Thu 8/64:00 pm
EYW
- ORD
Nonstop3h 55m
United Airlines
Deal found 4/30![United Airlines logo]()
$478
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/206:35 am
ORD
- EYW
1 stop7h 20m
Delta
Mon 6/227:50 am
EYW
- ORD
1 stop7h 26m
Delta
Deal found 5/2![Delta logo]()
$384
This Delta deal was found by Cheapflights users on 5/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/215:30 am
ORD
- EYW
1 stop6h 58m
Delta
Tue 6/3011:48 am
EYW
- ORD
1 stop6h 16m
Delta
Deal found 5/3![Delta logo]()
$414
This United Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/810:45 am
ORD
- EYW
Nonstop3h 24m
United Airlines
Fri 6/122:26 pm
EYW
- ORD
1 stop8h 41m
United Airlines
Deal found 5/1![United Airlines logo]()
$577
This United Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
ORD
- EYW
1 stop6h 30m
United Airlines
Tue 6/92:26 pm
EYW
- ORD
2 stops19h 40m
United Airlines
Deal found 4/29![United Airlines logo]()
$591
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/247:05 am
ORD
- EYW
1 stop4h 55m
Delta
Wed 5/2711:48 am
EYW
- ORD
1 stop7h 53m
Delta
Deal found 5/1![Delta logo]()
$587
Last-minute flights from O'Hare Intl to Key WestDiscover last-minute flight deals from O'Hare Intl to Key West. Data last updated May 4, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Key West. Data last updated May 4, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/98:30 am
ORD
- EYW
1 stop24h 54m
Multiple Airlines
Wed 5/1311:46 am
EYW
- ORD
1 stop22h 41m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/98:30 am
ORD
- EYW
1 stop24h 54m
Multiple Airlines
Tue 5/121:14 pm
EYW
- ORD
1 stop24h 09m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/131:59 pm
ORD
- EYW
2 stops19h 25m
Multiple Airlines
Fri 5/151:11 pm
EYW
- ORD
1 stop24h 12m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$337
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Fri 5/151:50 pm
ORD
- EYW
Nonstop3h 26m
American Airlines
Thu 5/214:19 pm
EYW
- ORD
Nonstop3h 53m
American Airlines
Deal found 4/30![American Airlines logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Thu 5/285:11 pm
ORD
- EYW
1 stop17h 16m
Multiple Airlines
Mon 6/11:11 pm
EYW
- ORD
2 stops31h 18m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/21:29 pm
ORD
- EYW
2 stops20h 37m
Multiple Airlines
Sat 6/62:48 pm
EYW
- ORD
1 stop22h 35m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$327
This American Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/311:46 am
ORD
- EYW
Nonstop3h 27m
American Airlines
Tue 6/94:17 pm
EYW
- ORD
Nonstop3h 48m
American Airlines
Deal found 4/29![American Airlines logo]()
$336
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/68:10 am
ORD
- EYW
1 stop4h 59m
Delta
Mon 6/86:24 pm
EYW
- ORD
1 stop6h 35m
Delta
Deal found 4/29![Delta logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/138:00 pm
ORD
- EYW
2 stops36h 41m
Multiple Airlines
Tue 6/301:14 pm
EYW
- ORD
1 stop7h 25m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$343
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 May 4, 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 May 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:11 pm
ORD
- EYW
1 stop19h 13m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$87
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 5/305:11 pm
ORD
- EYW
1 stop17h 14m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:11 pm
ORD
- EYW
1 stop17h 14m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Tue 5/266:55 am
ORD
- EYW
2 stops27h 11m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Tue 6/21:29 pm
ORD
- EYW
2 stops20h 37m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/251:50 pm
ORD
- EYW
2 stops21h 44m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Sat 6/208:00 pm
ORD
- EYW
2 stops36h 41m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:11 pm
ORD
- EYW
1 stop17h 16m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$144
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 May 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $327 (Kiwi.com) |
One-way from | $87 (Kiwi.com) |
Popular in | March |
Cheapest in | July |
Average price | $409 |
Good round-trip deal | $395 or less |
Good one-way deal | $283 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 2,558,603 searches. Data last updated May 4, 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 - EYW
ORDEYW
Chicago O'Hare Intl
Fri 6/5
9:49 am-5:23 pm
1 stop6h 34m
Key West
Mon 6/8
6:24 pm-11:59 pm
1 stop6h 35m
$329
ChicagoKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Mon 6/8
5:30 am-1:28 pm
1 stop6h 58m
Key West
Sat 6/13
7:50 am-2:14 pm
1 stop7h 24m
$329
ChicagoKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Thu 7/23
9:45 am-5:23 pm
1 stop6h 38m
Key West
Sun 8/2
6:18 pm-11:53 pm
1 stop6h 35m
$329
ChicagoKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Thu 7/30
1:44 pm-7:51 pm
1 stop5h 07m
Key West
Sun 8/2
11:56 am-6:45 pm
1 stop7h 49m
$354
ChicagoKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Sat 6/20
6:35 am-2:55 pm
1 stop7h 20m
Key West
Mon 6/22
7:50 am-2:16 pm
1 stop7h 26m
$384
ChicagoKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Sun 6/21
5:30 am-1:28 pm
1 stop6h 58m
Key West
Tue 6/30
11:48 am-5:04 pm
1 stop6h 16m
$414
ChicagoKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Sat 7/4
10:55 am-3:19 pm
Nonstop3h 24m
Key West
Wed 7/8
2:26 pm-9:00 pm
1 stop7h 34m
$464
Quickest round-trip
ChicagoKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Tue 7/28
10:43 am-3:07 pm
Nonstop3h 24m
Key West
Thu 8/6
4:00 pm-6:55 pm
Nonstop3h 55m
$478
ChicagoKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Mon 6/8
10:45 am-3:09 pm
Nonstop3h 24m
Key West
Fri 6/12
2:26 pm-10:07 pm
1 stop8h 41m
$577
ChicagoKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Sun 5/24
7:05 am-1:00 pm
1 stop4h 55m
Key West
Wed 5/27
11:48 am-6:41 pm
1 stop7h 53m
$587
Showing 1-10 of 23 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 May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | 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
Prices
Airlines
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, July is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Key West (average of $375). Flying from Chicago O'Hare Intl Airport to Key West in March is currently the most expensive (average of $549). 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 May 4, 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
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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 May 4, 2026.
Read reviews from past customers who have flown Delta,United Airlines, andAmerican 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.
Food
7.2
Overall
7.9
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.9
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Food
7.2
Overall
7.9
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.9
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Food
7.2
Overall
7.9
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.9
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Food
7.2
Overall
7.9
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.9
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Food
7.2
Overall
7.9
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.9
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl to Key West. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Other flights to Key West
Explore flights to Key West departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 4, 2026.
O'Hare Intl and Key West flights
Browse other O'Hare Intl and Key West flight options. Last updated on May 4, 2026.
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Top 4 airlines flying from O'Hare Intl to Key West
Discover the top 4 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 2,558,603 searches. Data last updated May 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$145 | Average$376 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$206 | Average$360 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$249 | Average$419 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$311 | Average$469 | FlexibilityNo cancel fee | On-time71% |