$113+ 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Oct 17 — Oct 241
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 May, 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 September 17, 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 September 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 11/236:30 am -
1 stop25h 54m
Thu 12/1012:01 pm -
1 stop11h 13m
Deal found 9/16![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/289:51 am -
1 stop25h 47m
Tue 11/31:16 pm -
2 stops24h 35m
Deal found 9/16![Multiple Airlines logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Wed 10/289:51 am -
1 stop25h 47m
Sat 10/3110:04 am -
2 stops9h 12m
Deal found 9/15![Multiple Airlines logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/277:15 am -
2 stops25h 09m
Sun 11/110:59 am -
1 stop22h 47m
Deal found 9/15![Multiple Airlines logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Wed 10/289:51 am -
1 stop23h 28m
Fri 10/3010:59 am -
1 stop22h 47m
Deal found 9/15![Multiple Airlines logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/136:00 am -
2 stops26h 24m
Mon 10/1910:59 am -
1 stop21h 52m
Deal found 9/16![Multiple Airlines logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/67:11 am -
2 stops25h 13m
Fri 10/910:59 am -
1 stop21h 52m
Deal found 9/16![Multiple Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Wed 10/289:51 am -
1 stop25h 47m
Sun 11/110:59 am -
1 stop22h 47m
Deal found 9/15![Multiple Airlines logo]()
$272
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 11/236:30 am -
1 stop25h 54m
Mon 11/304:09 pm -
2 stops39h 56m
Deal found 9/16![Multiple Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Wed 10/289:51 am -
1 stop25h 47m
Mon 11/22:44 pm -
2 stops23h 07m
Deal found 9/15![Multiple Airlines logo]()
$283
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 September 17, 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 September 17, 2026.
This Delta deal was found by Cheapflights users on 9/15. 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 12/155:30 am -
1 stop6h 41m
Sun 12/206:20 pm -
1 stop6h 39m
Deal found 9/15![Delta logo]()
$379
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Sun 1/1010:25 am -
Nonstop3h 47m
Sat 1/165:51 pm -
Nonstop3h 49m
Deal found 9/16![United Airlines logo]()
$515
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Thu 12/177:00 am -
Nonstop3h 41m
Sat 12/194:52 pm -
1 stop7h 32m
Deal found 9/15![United Airlines logo]()
$525
This United Airlines deal was found by Cheapflights users on 9/15. 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 1/59:22 pm -
2 stops15h 46m
Thu 1/143:04 pm -
1 stop8h 11m
Deal found 9/15![United Airlines logo]()
$564
This Delta deal was found by Cheapflights users on 9/14. 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 11/71:23 pm -
1 stop5h 38m
Tue 11/107:25 am -
2 stops10h 16m
Deal found 9/14![Delta logo]()
$719
This Delta deal was found by Cheapflights users on 9/15. 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.
Fri 1/17:00 am -
2 stops9h 24m
Wed 1/66:00 pm -
1 stop6h 50m
Deal found 9/15![Delta logo]()
$719
This United Airlines deal was found by Cheapflights users on 9/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2911:00 am -
Nonstop3h 29m
Mon 11/24:10 pm -
Nonstop3h 50m
Deal found 9/12![United Airlines logo]()
$757
This Delta deal was found by Cheapflights users on 9/11. 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.
Fri 11/207:05 am -
2 stops9h 05m
Tue 11/246:05 pm -
1 stop6h 49m
Deal found 9/11![Delta logo]()
$839
This United Airlines deal was found by Cheapflights users on 9/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/149:30 pm -
2 stops18h 32m
Sat 2/206:20 pm -
1 stop5h 55m
Deal found 9/12![United Airlines logo]()
$781
This United Airlines deal was found by Cheapflights users on 9/11. 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 10/311:00 am -
Nonstop3h 24m
Mon 10/52:15 pm -
1 stop9h 13m
Deal found 9/11![United Airlines logo]()
$785
This United Airlines deal was found by Cheapflights users on 9/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2812:25 pm -
Nonstop3h 46m
Mon 1/43:50 pm -
1 stop8h 49m
Deal found 9/12![United Airlines logo]()
$925
Last-minute flights from O'Hare Intl to Key WestDiscover last-minute flight deals from O'Hare Intl to Key West. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Key West. Data last updated September 17, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/67:11 am -
2 stops25h 13m
Fri 10/910:59 am -
1 stop21h 52m
Deal found 9/16![Multiple Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Wed 10/76:20 am -
2 stops26h 59m
Mon 10/1210:59 am -
1 stop21h 52m
Deal found 9/14![Multiple Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Mon 10/2610:26 am -
2 stops25h 10m
Fri 10/3010:59 am -
1 stop22h 47m
Deal found 9/15![Multiple Airlines logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/277:15 am -
2 stops25h 09m
Sun 11/110:59 am -
1 stop22h 47m
Deal found 9/15![Multiple Airlines logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Wed 10/289:51 am -
1 stop25h 47m
Tue 11/31:16 pm -
2 stops24h 35m
Deal found 9/15![Multiple Airlines logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Wed 10/289:51 am -
1 stop25h 47m
Sat 10/3110:04 am -
2 stops9h 12m
Deal found 9/15![Multiple Airlines logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Wed 10/289:51 am -
1 stop23h 28m
Fri 10/3010:59 am -
1 stop22h 47m
Deal found 9/15![Multiple Airlines logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Wed 10/289:51 am -
1 stop25h 47m
Sun 11/110:59 am -
1 stop22h 47m
Deal found 9/15![Multiple Airlines logo]()
$272
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Wed 10/289:51 am -
1 stop25h 47m
Mon 11/22:44 pm -
2 stops23h 07m
Deal found 9/15![Multiple Airlines logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/2910:26 am -
2 stops22h 53m
Sun 11/110:59 am -
1 stop22h 47m
Deal found 9/16![Multiple Airlines logo]()
$299
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 September 17, 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 September 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 12/148:00 am -
1 stop27h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/138:04 am -
2 stops24h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 11/177:15 am -
2 stops25h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Wed 11/117:15 am -
2 stops27h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 11/168:00 am -
2 stops27h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 9/16. 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 11/147:20 pm -
2 stops39h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Tue 12/159:21 pm -
2 stops11h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 11/37:15 am -
2 stops25h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Multiple Airlines logo]()
$142
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 September 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $215 (Kiwi.com) |
One-way from | $113 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $397 |
Good round-trip deal | $397 or less |
Good one-way deal | $288 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 September 17, 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
Tue 10/13
6:00 am-9:24 am
2 stops26h 24m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$136
ChicagoKey West
ORD Chicago O'Hare Intl - EYW Key West
ORDEYW
Chicago O'Hare Intl
Fri 10/9
10:26 am-9:24 am
2 stops21h 58m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$166
ChicagoKey West
ORD Chicago O'Hare Intl - EYW Key West
ORDEYW
Chicago O'Hare Intl
Sat 10/10
6:00 am-10:19 am
3 stops27h 19m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$198
ChicagoKey West
ORD Chicago O'Hare Intl - EYW Key West
ORDEYW
Chicago O'Hare Intl
Wed 10/14
7:40 am-11:21 am
3 stops26h 41m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$203
ChicagoKey West
ORD Chicago O'Hare Intl - EYW Key West
ORDEYW
Chicago O'Hare Intl
Sat 11/21
5:26 pm-11:21 am
3 stops16h 55m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$220
Quickest round-trip
ChicagoKey West
ORD Chicago O'Hare Intl - EYW Key West
ORDEYW
Chicago O'Hare Intl
Sun 12/13
7:00 am-11:24 am
Nonstop3h 24m
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
6:49 am-12:59 pm
1 stop5h 10m
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 10/13
10:44 am-5:15 pm
1 stop5h 31m
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 12/15
6:49 am-1:11 pm
1 stop5h 22m
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 11/9
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 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 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 $516). 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.
How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Key West?
Airfare is below average for this route at the moment.
Chicago O'Hare Intl Airport to Key West flights typically cost between $333 and $468 in November.The cheapest round-trip price found within the last 5 days was $215 on Multiple Airlines (Nov 23-Dec 10).
The best insider tips for Chicago O'Hare Intl Airport to Key West flights
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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 September 17, 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.
Overall
7.8
Boarding
8.1
Entertainment
7.8
Crew
8.5
Comfort
7.8
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Overall
7.8
Boarding
8.1
Entertainment
7.8
Crew
8.5
Comfort
7.8
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Overall
7.8
Boarding
8.1
Entertainment
7.8
Crew
8.5
Comfort
7.8
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Overall
7.8
Boarding
8.1
Entertainment
7.8
Crew
8.5
Comfort
7.8
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Related info for your journey
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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 September 17, 2026.
O'Hare Intl and Key West flights
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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 September 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$196 | Average$368 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$249 | Average$410 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$304 | Average$474 | FlexibilityNo cancel fee | On-time71% |