₩497,000 Cheap Flights from Chicago (ORD) to Key West (EYW)

View ₩497,000 flight on Sun, Dec 21, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at ₩497,000 for one-way flights and ₩643,300 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Thu, Dec 25 - Mon, Dec 29
ORD
Chicago
EYW
Key West
₩643,300 Roundtrip, found 6 days ago
₩643,300
Roundtrip
found 6 days ago
Select United flight, departing Thu, Dec 25 from Chicago to Key West, returning Mon, Dec 29, priced at ₩643,300 found 6 days ago
United
Thu, Dec 25 - Mon, Dec 29
ORD
Chicago
EYW
Key West
₩657,700 Roundtrip, found 6 days ago
₩657,700
Roundtrip
found 6 days ago
Select United flight, departing Thu, Dec 25 from Chicago to Key West, returning Mon, Dec 29, priced at ₩657,700 found 6 days ago
United
Thu, Dec 25 - Mon, Dec 29
ORD
Chicago
EYW
Key West
₩687,300 Roundtrip, found 6 days ago
₩687,300
Roundtrip
found 6 days ago
Select United flight, departing Thu, Dec 25 from Chicago to Key West, returning Mon, Dec 29, priced at ₩687,300 found 6 days ago
United
Thu, Dec 25 - Mon, Dec 29
ORD
Chicago
EYW
Key West
₩701,700 Roundtrip, found 6 days ago
₩701,700
Roundtrip
found 6 days ago
Select United flight, departing Thu, Dec 25 from Chicago to Key West, returning Mon, Dec 29, priced at ₩701,700 found 6 days ago
United
Thu, Dec 25 - Mon, Dec 29
ORD
Chicago
EYW
Key West
₩716,100 Roundtrip, found 6 days ago
₩716,100
Roundtrip
found 6 days ago
Select United flight, departing Thu, Dec 25 from Chicago to Key West, returning Mon, Dec 29, priced at ₩716,100 found 6 days ago
United
Thu, Dec 25 - Mon, Dec 29
ORD
Chicago
EYW
Key West
₩732,800 Roundtrip, found 6 days ago
₩732,800
Roundtrip
found 6 days ago
Select United flight, departing Thu, Dec 25 from Chicago to Key West, returning Mon, Dec 29, priced at ₩732,800 found 6 days ago
United
Sun, Dec 21 - Thu, Dec 25
ORD
Chicago
EYW
Key West
₩766,600 Roundtrip, found 6 days ago
₩766,600
Roundtrip
found 6 days ago
Select United flight, departing Sun, Dec 21 from Chicago to Key West, returning Thu, Dec 25, priced at ₩766,600 found 6 days ago
United
Thu, Dec 25 - Mon, Dec 29
ORD
Chicago
EYW
Key West
₩776,900 Roundtrip, found 6 days ago
₩776,900
Roundtrip
found 6 days ago
Select United flight, departing Thu, Dec 25 from Chicago to Key West, returning Mon, Dec 29, priced at ₩776,900 found 6 days ago
American Airlines
Sun, Dec 21 - Thu, Dec 25
ORD
Chicago
EYW
Key West
₩891,300 Roundtrip, found 6 days ago
₩891,300
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sun, Dec 21 from Chicago to Key West, returning Thu, Dec 25, priced at ₩891,300 found 6 days ago
Delta
Sun, Dec 21 - Thu, Dec 25
ORD
Chicago
EYW
Key West
₩938,000 Roundtrip, found 6 days ago
₩938,000
Roundtrip
found 6 days ago
Select Delta flight, departing Sun, Dec 21 from Chicago to Key West, returning Thu, Dec 25, priced at ₩938,000 found 6 days ago

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

January is typically the cheapest month to fly

From ₩284,226 - ₩643,620 per traveler.

Alternative airports near Key West

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Key West Intl. EYW. Cheapest and Closest option available. Average driving time to city center is 8 minutes. Flights from ₩643,300
EYW
Key West Intl.
CheapestClosest
Average driving time to city center8 min
Flights from ₩643,300
Flights from Chicago (ORD) to Key West (EYW)
Origin airport
O'Hare Intl.
Destination airport
Key West Intl.
Roundtrip price
₩643,300
Distance
2006 km
Average flight time
4 hours 26 mins

Chicago to Key West Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Chicago to Key West will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Key West.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with ORD to EYW flights that won’t make your bank account wince. Ready to temporarily leave behind Chicago for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to EYW with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

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 ₩643,300. 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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