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 $309 round trip and one way. Prices and availability subject to change. Additional terms may apply.

Fri, Jan 9 - Mon, Jan 12
ORD
Chicago
EYW
Key West
CA $309 Roundtrip, found 4 days ago
CA $309
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Fri, Jan 9 from Chicago to Key West, returning Mon, Jan 12, priced at CA $309 found 4 days ago
Fri, Jan 9 - Mon, Jan 12
ORD
Chicago
EYW
Key West
CA $310 Roundtrip, found 4 days ago
CA $310
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Fri, Jan 9 from Chicago to Key West, returning Mon, Jan 12, priced at CA $310 found 4 days ago
Fri, Jan 23 - Mon, Jan 26
ORD
Chicago
EYW
Key West
CA $339 Roundtrip, found 4 days ago
CA $339
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Fri, Jan 23 from Chicago to Key West, returning Mon, Jan 26, priced at CA $339 found 4 days 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.