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 $458 round trip and CA $405 one way. Prices and availability subject to change. Additional terms may apply.

Tue, Mar 31 - Wed, Apr 8
ORD
Chicago
EYW
Key West
CA $458 Roundtrip, found 1 day ago
CA $458
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Mar 31 from Chicago to Key West, returning Wed, Apr 8, priced at CA $458 found 1 day ago
Mon, Mar 30 - Wed, Apr 8
ORD
Chicago
EYW
Key West
CA $513 Roundtrip, found 1 day ago
CA $513
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Mar 30 from Chicago to Key West, returning Wed, Apr 8, priced at CA $513 found 1 day ago
Tue, Mar 31 - Fri, Apr 10
ORD
Chicago
EYW
Key West
CA $566 Roundtrip, found 1 day ago
CA $566
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Mar 31 from Chicago to Key West, returning Fri, Apr 10, priced at CA $566 found 1 day ago
Sat, Mar 28 - Wed, Apr 8
ORD
Chicago
EYW
Key West
CA $570 Roundtrip, found 1 day ago
CA $570
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Mar 28 from Chicago to Key West, returning Wed, Apr 8, priced at CA $570 found 1 day ago
Tue, Mar 31 - Fri, Apr 10
ORD
Chicago
EYW
Key West
CA $580 Roundtrip, found 1 day ago
CA $580
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Mar 31 from Chicago to Key West, returning Fri, Apr 10, priced at CA $580 found 1 day ago
Mon, Mar 30 - Fri, Apr 10
ORD
Chicago
EYW
Key West
CA $622 Roundtrip, found 1 day ago
CA $622
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Mar 30 from Chicago to Key West, returning Fri, Apr 10, priced at CA $622 found 1 day ago
Mon, Mar 30 - Fri, Apr 10
ORD
Chicago
EYW
Key West
CA $635 Roundtrip, found 1 day ago
CA $635
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Mar 30 from Chicago to Key West, returning Fri, Apr 10, priced at CA $635 found 1 day ago
Thu, Mar 26 - Wed, Apr 8
ORD
Chicago
EYW
Key West
CA $653 Roundtrip, found 1 day ago
CA $653
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Mar 26 from Chicago to Key West, returning Wed, Apr 8, priced at CA $653 found 1 day ago
Sat, Mar 28 - Wed, Apr 8
ORD
Chicago
EYW
Key West
CA $674 Roundtrip, found 1 day ago
CA $674
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Mar 28 from Chicago to Key West, returning Wed, Apr 8, priced at CA $674 found 1 day ago
Sun, Mar 29 - Wed, Apr 8
ORD
Chicago
EYW
Key West
CA $676 Roundtrip, found 1 day ago
CA $676
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Mar 29 from Chicago to Key West, returning Wed, Apr 8, priced at CA $676 found 1 day 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.