$141 Cheap Flights from Chicago (ORD) to Key West (EYW)

View $141 flight on Thu, Jul 3, 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 available prices by choosing your travel dates.

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

Prices were available within the past 7 days and start at $141 for one-way flights and $249 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, Aug 15 - Tue, Aug 19
ORD
Chicago
EYW
Key West
$249 Roundtrip, just found
$249
Roundtrip
just found
Select Delta flight, departing Fri, Aug 15 from Chicago to Key West, returning Tue, Aug 19, priced at $249 just found
Delta
Tue, Aug 5 - Tue, Aug 12
ORD
Chicago
EYW
Key West
$269 Roundtrip, found 6 hours ago
$269
Roundtrip
found 6 hours ago
Select Delta flight, departing Tue, Aug 5 from Chicago to Key West, returning Tue, Aug 12, priced at $269 found 6 hours ago
American Airlines
Mon, Jun 30 - Wed, Jul 2
ORD
Chicago
EYW
Key West
$270 Roundtrip, found 16 hours ago
$270
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Mon, Jun 30 from Chicago to Key West, returning Wed, Jul 2, priced at $270 found 16 hours ago
American Airlines
Mon, Jun 30 - Wed, Jul 2
ORD
Chicago
EYW
Key West
$275 Roundtrip, found 16 hours ago
$275
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Mon, Jun 30 from Chicago to Key West, returning Wed, Jul 2, priced at $275 found 16 hours ago
Delta
Sat, Aug 2 - Wed, Aug 6
ORD
Chicago
EYW
Key West
$286 Roundtrip, found 1 hour ago
$286
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, Aug 2 from Chicago to Key West, returning Wed, Aug 6, priced at $286 found 1 hour ago
Delta
Fri, Aug 15 - Tue, Aug 19
ORD
Chicago
EYW
Key West
$289 Roundtrip, just found
$289
Roundtrip
just found
Select Delta flight, departing Fri, Aug 15 from Chicago to Key West, returning Tue, Aug 19, priced at $289 just found
American Airlines
Mon, Jun 30 - Mon, Jul 7
ORD
Chicago
EYW
Key West
$295 Roundtrip, found 5 hours ago
$295
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Mon, Jun 30 from Chicago to Key West, returning Mon, Jul 7, priced at $295 found 5 hours ago
American Airlines
Thu, Jul 3 - Tue, Jul 8
ORD
Chicago
EYW
Key West
$296 Roundtrip, just found
$296
Roundtrip
just found
Select American Airlines flight, departing Thu, Jul 3 from Chicago to Key West, returning Tue, Jul 8, priced at $296 just found
United
Thu, Nov 13 - Sat, Nov 15
ORD
Chicago
EYW
Key West
$306 Roundtrip, found 23 hours ago
$306
Roundtrip
found 23 hours ago
Select United flight, departing Thu, Nov 13 from Chicago to Key West, returning Sat, Nov 15, priced at $306 found 23 hours ago
JetBlue Airways
Tue, Oct 21 - Fri, Oct 24
ORD
Chicago
EYW
Key West
$403 Roundtrip, found 2 hours ago
$403
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Tue, Oct 21 from Chicago to Key West, returning Fri, Oct 24, priced at $403 found 2 hours ago

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW) cost?
You can find cheap return flights from O’Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW) starting from $364. Grab your seat and start your adventure. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a American Airlines flight leaving ORD on May 19 2025 and touching down at EYW. The price was last updated on April 22 2025 and has not changed since.
What is the cheapest month to fly from ORD to EYW?
The cheapest flights from ORD to EYW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)?
You can travel nonstop from O’Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW) on an American Airlines flight.
What is the cheapest airline that flies from ORD to EYW?
Take off from ORD to EYW with American Airlines. This airline currently offers the lowest one-way fare on this route, starting from $152. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on May 20 2025. Prices were last updated on April 22 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)?
When jetting out of O’Hare Intl. Airport (ORD), you’ll have your pick from an average of 2 daily nonstop flights to Key West Intl. Airport (EYW).
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)?
The 10 AM departures from ORD to EYW are the busiest. Greater demand means you’ll likely pay more for these departures. If you want to save on your fare, book during off-peak hours.
What day of the week has the most flights from ORD to EYW?
Sunday offers the most flights from O’Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW). Consider jetting off on this day and you’ll have a greater chance of finding a departure that fits your schedule.
What is the earliest flight from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)?
Catch the earliest flight at around 8:10AM UTC-6, leaving from O’Hare Intl. Airport (ORD). You’ll be flying for approximately 3h 24m, reaching Key West Intl. Airport (EYW) at approximately 12:34PM UTC-5.
How long does it take to fly from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)?
It usually takes 3 hours and 16 minutes to travel the 1,250 mi from ORD to EYW.
What airline has the least delays from ORD to EYW?
United Airlines has the best track record for on-time direct flights from O’Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW), with an on-time score of 85%. Use the Expedia App to look up your journey status before you leave and get real-time updates about any trip changes.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)?
To avoid potential delays on the O’Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW) route, aim to fly before 3 PM. Later departures have a 22% higher chance of cancellation.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Key West from O'Hare Intl. Airport (ORD)?
Key West Intl. Airport (EYW) is the only airport in Key West with direct flights from O’Hare Intl. Airport (ORD). Check out your options and discover affordable fares on Expedia.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW) last-minute?
Last-minute fares from ORD to EYW are usually more expensive. To secure the lowest rates, start looking for flights early. That said, if you’re flexible with your travel dates, you may find a cheap ticket right before your journey.
Is it cheaper to book an ORD to EYW flight and hotel package?
You can save money by securing an ORD to EYW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it’s easy to manage everything in one place. Once you’ve chosen your preferred accommodations and flights, consider other add-ons like activities, tours and car rentals.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)?
Typically, it’s possible to reschedule or cancel your ORD to EYW flight. However, for bookings made more than 24 hours ago, additional fees may apply. Check your airline’s policies in your itinerary to see what changes are allowed and if any costs are involved. You’ll also find further details on our Customer Service portal.
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