￥52,820 Cheap Flights from Chicago (ORD) to Key West (EYW)

View ￥52,820 flight on Sun, Jan 4, 2026Opens 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 ￥52,820 for one-way flights and ￥46,540 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Jan 6 - Wed, Jan 14
ORD
Chicago
EYW
Key West
￥46,540 Roundtrip, found 5 days ago
￥46,540
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Jan 6 from Chicago to Key West, returning Wed, Jan 14, priced at ￥46,540 found 5 days ago
Delta
Tue, Jan 6 - Tue, Jan 13
ORD
Chicago
EYW
Key West
￥50,410 Roundtrip, found 5 days ago
￥50,410
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Jan 6 from Chicago to Key West, returning Tue, Jan 13, priced at ￥50,410 found 5 days ago
Delta
Mon, Jan 5 - Wed, Jan 14
ORD
Chicago
EYW
Key West
￥52,030 Roundtrip, found 5 days ago
￥52,030
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Jan 5 from Chicago to Key West, returning Wed, Jan 14, priced at ￥52,030 found 5 days ago
Delta
Sat, Jan 3 - Wed, Jan 14
ORD
Chicago
EYW
Key West
￥52,130 Roundtrip, found 5 days ago
￥52,130
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Jan 3 from Chicago to Key West, returning Wed, Jan 14, priced at ￥52,130 found 5 days ago
Delta
Thu, Jan 1 - Wed, Jan 14
ORD
Chicago
EYW
Key West
￥54,990 Roundtrip, found 5 days ago
￥54,990
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Jan 1 from Chicago to Key West, returning Wed, Jan 14, priced at ￥54,990 found 5 days ago
Delta
Fri, Jan 2 - Wed, Jan 14
ORD
Chicago
EYW
Key West
￥55,140 Roundtrip, found 5 days ago
￥55,140
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Jan 2 from Chicago to Key West, returning Wed, Jan 14, priced at ￥55,140 found 5 days ago
Delta
Mon, Jan 5 - Tue, Jan 13
ORD
Chicago
EYW
Key West
￥55,900 Roundtrip, found 5 days ago
￥55,900
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Jan 5 from Chicago to Key West, returning Tue, Jan 13, priced at ￥55,900 found 5 days ago
Delta
Sat, Jan 3 - Tue, Jan 13
ORD
Chicago
EYW
Key West
￥56,110 Roundtrip, found 5 days ago
￥56,110
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Jan 3 from Chicago to Key West, returning Tue, Jan 13, priced at ￥56,110 found 5 days ago
United
Thu, Jan 1 - Tue, Jan 13
ORD
Chicago
EYW
Key West
￥57,060 Roundtrip, found 5 days ago
￥57,060
Roundtrip
found 5 days ago
Select United flight, departing Thu, Jan 1 from Chicago to Key West, returning Tue, Jan 13, priced at ￥57,060 found 5 days ago
American Airlines
Sun, Jan 4 - Mon, Jan 12
ORD
Chicago
EYW
Key West
￥62,220 Roundtrip, found 5 days ago
￥62,220
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sun, Jan 4 from Chicago to Key West, returning Mon, Jan 12, priced at ￥62,220 found 5 days ago

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

January is typically the cheapest month to fly

From ￥30,051 - ￥68,050 per traveler.
Flights from Chicago (ORD) to Key West (EYW)
Origin airport
O'Hare Intl.
Destination airport
Key West Intl.
Roundtrip price
￥46,540
Distance
2006 km
Average flight time
4 hours 30 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 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 EYW?
The lowest price advertised for a round-trip journey between O'Hare Intl. Airport (ORD) and Key West Intl. Airport (EYW) is ￥46,540. But you better get a move on. This figure is based on fares offered within the last 7 days on Expedia for flights departing within the next year. 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 (EYW)?
Most flights can be conveniently canceled online, but whether or not you incur a fee varies between airlines. If you do need to cancel your trip, follow the instructions in the Customer Service Portal.
How do I find cheap flights from O'Hare Airport 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 ORD to EYW flights, you'll see a "no change fees" filter for you to select.
How many hours is the flight from O'Hare Intl. Airport (ORD) to Key West Intl. Airport?
You may like to bring your own entertainment (like some downloaded TV shows), as it takes about 4 hours and 31 minutes to arrive at EYW from ORD. A good pair of noise-canceling headphones will be useful too.
How far is the flight from ORD to Key West Intl. Airport?
Around 2,000 kilometers separates Chicago and Key West, so pack something to help you fill in a few hours. That gripping novel you haven't had time to start will be perfect.
Which airlines fly direct from O'Hare Airport to Key West Intl. Airport?
There are no direct flights, so you'll have to make at least one stop between ORD and Key West Intl. Airport (EYW). Take advantage of the layover time to stretch your legs and take a break.
Are ORD to EYW flight tickets cheaper when they're purchased at the last minute?
Flight prices fluctuate, so it's no sure thing. While last-minute flight deals between O'Hare Airport and Key West Intl. Airport (EYW) are possible, it's also a good idea to monitor prices well before you fly. In fact, some air carriers advertise their prices up to a year ahead of the departure date. Expedia is continuously updating the biggest airfare bargains around, so keep checking and be ready to secure your seat when the price is low.

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