Cheap Flights From O'Hare Intl. (ORD) To Key West Intl. (EYW)

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Cheapest Flights from Chicago (ORD) to Key West (EYW)

The cheapest flights to Key West Intl. found within the past 7 days were CA $402 round trip and one way. Prices and availability subject to change. Additional terms may apply.

Tue, Dec. 16 - Mon, Dec. 22
ORD
Chicago
EYW
Key West
CA $402 Roundtrip, found 9 hours ago
CA $402
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Dec. 16 from Chicago to Key West, returning Mon, Dec. 22, priced at CA $402 found 9 hours ago
Tue, Dec. 16 - Mon, Dec. 22
ORD
Chicago
EYW
Key West
CA $429 Roundtrip, found 9 hours ago
CA $429
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Dec. 16 from Chicago to Key West, returning Mon, Dec. 22, priced at CA $429 found 9 hours ago
Tue, Dec. 16 - Mon, Dec. 22
ORD
Chicago
EYW
Key West
CA $472 Roundtrip, found 9 hours ago
CA $472
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Dec. 16 from Chicago to Key West, returning Mon, Dec. 22, priced at CA $472 found 9 hours ago
Tue, Dec. 16 - Mon, Dec. 22
ORD
Chicago
EYW
Key West
CA $480 Roundtrip, found 9 hours ago
CA $480
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Dec. 16 from Chicago to Key West, returning Mon, Dec. 22, priced at CA $480 found 9 hours ago
Tue, Dec. 16 - Mon, Dec. 22
ORD
Chicago
EYW
Key West
CA $493 Roundtrip, found 9 hours ago
CA $493
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Dec. 16 from Chicago to Key West, returning Mon, Dec. 22, priced at CA $493 found 9 hours ago
Tue, Dec. 16 - Mon, Dec. 22
ORD
Chicago
EYW
Key West
CA $506 Roundtrip, found 9 hours ago
CA $506
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Dec. 16 from Chicago to Key West, returning Mon, Dec. 22, priced at CA $506 found 9 hours ago
Tue, Dec. 16 - Mon, Dec. 22
ORD
Chicago
EYW
Key West
CA $513 Roundtrip, found 9 hours ago
CA $513
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Dec. 16 from Chicago to Key West, returning Mon, Dec. 22, priced at CA $513 found 9 hours ago
Tue, Dec. 16 - Mon, Dec. 22
ORD
Chicago
EYW
Key West
CA $527 Roundtrip, found 9 hours ago
CA $527
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Dec. 16 from Chicago to Key West, returning Mon, Dec. 22, priced at CA $527 found 9 hours ago
Tue, Dec. 16 - Mon, Dec. 22
ORD
Chicago
EYW
Key West
CA $529 Roundtrip, found 9 hours ago
CA $529
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Dec. 16 from Chicago to Key West, returning Mon, Dec. 22, priced at CA $529 found 9 hours ago
Tue, Dec. 16 - Mon, Dec. 22
ORD
Chicago
EYW
Key West
CA $533 Roundtrip, found 9 hours ago
CA $533
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Dec. 16 from Chicago to Key West, returning Mon, Dec. 22, priced at CA $533 found 9 hours ago
Tue, Dec. 16 - Mon, Dec. 22
ORD
Chicago
EYW
Key West
CA $540 Roundtrip, found 9 hours ago
CA $540
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Dec. 16 from Chicago to Key West, returning Mon, Dec. 22, priced at CA $540 found 9 hours ago
Tue, Dec. 16 - Mon, Dec. 22
ORD
Chicago
EYW
Key West
CA $541 Roundtrip, found 9 hours ago
CA $541
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Dec. 16 from Chicago to Key West, returning Mon, Dec. 22, priced at CA $541 found 9 hours ago
Tue, Dec. 16 - Mon, Dec. 22
ORD
Chicago
EYW
Key West
CA $542 Roundtrip, found 9 hours ago
CA $542
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Dec. 16 from Chicago to Key West, returning Mon, Dec. 22, priced at CA $542 found 9 hours ago
Tue, Dec. 16 - Mon, Dec. 22
ORD
Chicago
EYW
Key West
CA $562 Roundtrip, found 9 hours ago
CA $562
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Dec. 16 from Chicago to Key West, returning Mon, Dec. 22, priced at CA $562 found 9 hours ago
Tue, Dec. 16 - Mon, Dec. 22
ORD
Chicago
EYW
Key West
CA $576 Roundtrip, found 9 hours ago
CA $576
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Dec. 16 from Chicago to Key West, returning Mon, Dec. 22, priced at CA $576 found 9 hours ago
Tue, Dec. 16 - Mon, Dec. 22
ORD
Chicago
EYW
Key West
CA $584 Roundtrip, found 9 hours ago
CA $584
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Dec. 16 from Chicago to Key West, returning Mon, Dec. 22, priced at CA $584 found 9 hours ago
Tue, Dec. 16 - Mon, Dec. 22
ORD
Chicago
EYW
Key West
CA $591 Roundtrip, found 9 hours ago
CA $591
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Dec. 16 from Chicago to Key West, returning Mon, Dec. 22, priced at CA $591 found 9 hours ago
Tue, Dec. 16 - Mon, Dec. 22
ORD
Chicago
EYW
Key West
CA $604 Roundtrip, found 9 hours ago
CA $604
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Dec. 16 from Chicago to Key West, returning Mon, Dec. 22, priced at CA $604 found 9 hours ago
Tue, Dec. 16 - Mon, Dec. 22
ORD
Chicago
EYW
Key West
CA $618 Roundtrip, found 9 hours ago
CA $618
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Dec. 16 from Chicago to Key West, returning Mon, Dec. 22, priced at CA $618 found 9 hours ago
Tue, Dec. 16 - Mon, Dec. 22
ORD
Chicago
EYW
Key West
CA $624 Roundtrip, found 9 hours ago
CA $624
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Dec. 16 from Chicago to Key West, returning Mon, Dec. 22, priced at CA $624 found 9 hours ago

Frequently asked questions

Are there direct flights from ORD to Key West Intl. Airport (EYW)?
If you want to journey from ORD to Key West Intl. Airport as quickly as possible, you'll be happy to know multiple airlines offer direct flights. Choose your preferred seat with United Airlines or American Airlines.
What airlines fly from O'Hare Airport to Key West Intl. Airport?
There are a number of airlines with direct flights from ORD to EYW. United Airlines (UA) is well-known, operating at least 43 flights every month. Another good option is American Airlines (AA), which has 17 flights every month. The more airlines you weigh up, the more likely you are to snag a fantastic deal.
What is the best day to buy a plane ticket?
Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you're looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you're browsing flight deals.
What are the cheapest days to fly?
Frequent travellers may already know this, but earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.
How far in advance can you book a flight?
Here's the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

Popular Flight Routes from Chicago (ORD)

Travelers at ORD love to visit these top cities. Roam to the top destinations from Chicago (ORD) today with the cheap prices from Travelocity!

Popular Flight Routes from Key West (EYW)

Travelers at EYW love to visit these top cities. Roam to the top destinations from Key West(EYW) today with the cheap prices from Travelocity!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.