Cheap Flights from Chicago (ORD) to Key West (EYW) from HK$2,069~

View HK$2,069 flight on Mon, 8 Dec 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)

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Find Cheap Flights from Chicago (ORD) to Key West (EYW)

Prices were available within the past 7 days and start at HK$2,069 for one-way flights and HK$4,137 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, 8 Dec - Fri, 12 Dec
ORD
Chicago
EYW
Key West
HK$4,137 Return, found 22 hours ago
HK$4,137
Return
found 22 hours ago
Select Delta flight, departing Mon, 8 Dec from Chicago to Key West, returning Fri, 12 Dec, priced at HK$4,137 found 22 hours ago
American Airlines
Mon, 8 Dec - Fri, 12 Dec
ORD
Chicago
EYW
Key West
HK$4,148 Return, found 22 hours ago
HK$4,148
Return
found 22 hours ago
Select American Airlines flight, departing Mon, 8 Dec from Chicago to Key West, returning Fri, 12 Dec, priced at HK$4,148 found 22 hours ago
Delta
Mon, 8 Dec - Fri, 12 Dec
ORD
Chicago
EYW
Key West
HK$4,266 Return, found 22 hours ago
HK$4,266
Return
found 22 hours ago
Select Delta flight, departing Mon, 8 Dec from Chicago to Key West, returning Fri, 12 Dec, priced at HK$4,266 found 22 hours ago
Delta
Mon, 8 Dec - Fri, 12 Dec
ORD
Chicago
EYW
Key West
HK$4,383 Return, found 22 hours ago
HK$4,383
Return
found 22 hours ago
Select Delta flight, departing Mon, 8 Dec from Chicago to Key West, returning Fri, 12 Dec, priced at HK$4,383 found 22 hours ago
American Airlines
Mon, 8 Dec - Fri, 12 Dec
ORD
Chicago
EYW
Key West
HK$4,393 Return, found 22 hours ago
HK$4,393
Return
found 22 hours ago
Select American Airlines flight, departing Mon, 8 Dec from Chicago to Key West, returning Fri, 12 Dec, priced at HK$4,393 found 22 hours ago
Delta
Mon, 8 Dec - Fri, 12 Dec
ORD
Chicago
EYW
Key West
HK$4,406 Return, found 22 hours ago
HK$4,406
Return
found 22 hours ago
Select Delta flight, departing Mon, 8 Dec from Chicago to Key West, returning Fri, 12 Dec, priced at HK$4,406 found 22 hours ago
American Airlines
Mon, 8 Dec - Fri, 12 Dec
ORD
Chicago
EYW
Key West
HK$4,416 Return, found 22 hours ago
HK$4,416
Return
found 22 hours ago
Select American Airlines flight, departing Mon, 8 Dec from Chicago to Key West, returning Fri, 12 Dec, priced at HK$4,416 found 22 hours ago
Delta
Mon, 8 Dec - Fri, 12 Dec
ORD
Chicago
EYW
Key West
HK$4,460 Return, found 22 hours ago
HK$4,460
Return
found 22 hours ago
Select Delta flight, departing Mon, 8 Dec from Chicago to Key West, returning Fri, 12 Dec, priced at HK$4,460 found 22 hours ago
American Airlines
Mon, 8 Dec - Fri, 12 Dec
ORD
Chicago
EYW
Key West
HK$4,470 Return, found 22 hours ago
HK$4,470
Return
found 22 hours ago
Select American Airlines flight, departing Mon, 8 Dec from Chicago to Key West, returning Fri, 12 Dec, priced at HK$4,470 found 22 hours ago
United
Mon, 8 Dec - Fri, 12 Dec
ORD
Chicago
EYW
Key West
HK$4,511 Return, found 22 hours ago
HK$4,511
Return
found 22 hours ago
Select United flight, departing Mon, 8 Dec from Chicago to Key West, returning Fri, 12 Dec, priced at HK$4,511 found 22 hours ago

Find the cheapest month to fly from Chicago (ORD) to Key West (EYW)

November is typically the cheapest month to fly

From HK$1,483 - HK$5,176 per traveller.

Graph displaying average flight prices per month

Chicago to Key West route information
Origin airport
O'Hare Intl.
Destination airport
Key West Intl.
Airlines serving
American Airlines, Delta, United
Return price
HK$4,137
Distance
2006 km
Average flight time
3 hours 11 mins

Flights from Chicago to Key West

Book cheap flights from Chicago (ORD) to Key West (EYW) on Expedia.com.hk. Find the best flight deals to destinations around the world for your next leisure or business travel on Expedia.com.hk.

Search for flights from Chicago (ORD) to Key West (EYW) to find great flight deals suitable to your travel date and time. Expedia.com.hk flight booking search engine is simple to use and looking for cheap flights is as easy as a click of a mouse or on your mobile devices.

Be assured that you’re seeing the best price guaranteed! Our friendly customer service representatives are here to serve you 24 hours day to provide assistance and answer any questions that you may have about booking your Chicago (ORD) to Key West (EYW) trip. Call us at 3077-4857 (direct number - 24 hours day for English).

Save more when combine your Key West flight with a hotel for a package deal! Discover additional savings by booking in advance. Now you can find activities in Key West and things to do in Key West for your perfect vacation with Expedia Thing to Do.

If you would like to book flights to Key West more flexibly, many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Key West is HK$2,069 now!

 

Frequently asked questions

How much is a flight from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)?
Start packing your suitcase, because round-trip flights between O'Hare Intl. Airport (ORD) and Key West Intl. Airport (EYW) start from HK$4,137. That's based on fares advertised within the last 7 days on Expedia for flights departing within the next year. Prices can change quickly, so book now to lock in the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from O'Hare Airport to Key West Intl. Airport?
This can differ between airlines, as each one has its own terms and conditions. Visit the Customer Service Portal, where there are easy-to-follow instructions on how to cancel online.
How do I find cheap flights from O'Hare Intl. Airport (ORD) to EYW that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for O'Hare Airport to EYW flights, you'll see a "no change fees" filter for you to select.
How far is the flight from O'Hare Airport to Key West Intl. Airport (EYW)?
You'll be soaring through the sky for a while, as the flight distance from Chicago to Key West is 2,000 kilometers. Put together a playlist of your favorite songs before you leave home to keep yourself entertained during the flight.
Which airlines fly direct from O'Hare Airport to EYW?
A popular option with many savvy travelers, American Airlines (AA) offers 21 flights every month from O'Hare Airport to Key West Intl. Airport (EYW). Pick the one that suits your travel plans and book your seat today.
Are O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW) flight tickets cheaper when they're purchased at the last minute?
It is possible to nab a fantastic last-minute deal from O'Hare Intl. Airport (ORD) to EYW, but it can also be hit-or-miss. As many airlines publish prices up to 12 months in advance, it's worth keeping an eye on fares early and being ready to pounce when you spot a bargain. Expedia compares air carrier prices and updates flight deals often, so you can rest assured you're always getting the latest offers.

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