$91 Cheap Flights from Chicago (ORD) to Key West (EYW)

View $91 flight on Wed, Jan 21, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at $91 for one-way flights and $181 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Wed, Jan 21 - Tue, Jan 27
ORD
Chicago
EYW
Key West
$181 Roundtrip, found 1 hour ago
$181
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Wed, Jan 21 from Chicago to Key West, returning Tue, Jan 27, priced at $181 found 1 hour ago
Spirit Airlines
Tue, Feb 3 - Tue, Feb 10
ORD
Chicago
EYW
Key West
$193 Roundtrip, found 2 days ago
$193
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Feb 3 from Chicago to Key West, returning Tue, Feb 10, priced at $193 found 2 days ago
Spirit Airlines
Thu, Jan 29 - Tue, Feb 3
ORD
Chicago
EYW
Key West
$197 Roundtrip, just found
$197
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Jan 29 from Chicago to Key West, returning Tue, Feb 3, priced at $197 just found
Spirit Airlines
Wed, Feb 25 - Mon, Mar 2
ORD
Chicago
EYW
Key West
$198 Roundtrip, found 5 hours ago
$198
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Wed, Feb 25 from Chicago to Key West, returning Mon, Mar 2, priced at $198 found 5 hours ago
Spirit Airlines
Fri, Jan 9 - Tue, Jan 13
ORD
Chicago
EYW
Key West
$202 Roundtrip, just found
$202
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Jan 9 from Chicago to Key West, returning Tue, Jan 13, priced at $202 just found
Spirit Airlines
Fri, Jan 23 - Tue, Jan 27
ORD
Chicago
EYW
Key West
$203 Roundtrip, found 4 hours ago
$203
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Fri, Jan 23 from Chicago to Key West, returning Tue, Jan 27, priced at $203 found 4 hours ago
United
Thu, Jun 11 - Thu, Jun 18
ORD
Chicago
EYW
Key West
$249 Roundtrip, just found
$249
Roundtrip
just found
Select United flight, departing Thu, Jun 11 from Chicago to Key West, returning Thu, Jun 18, priced at $249 just found
Delta
Thu, Jan 29 - Tue, Feb 3
ORD
Chicago
EYW
Key West
$269 Roundtrip, just found
$269
Roundtrip
just found
Select Delta flight, departing Thu, Jan 29 from Chicago to Key West, returning Tue, Feb 3, priced at $269 just found
American Airlines
Wed, Jan 21 - Tue, Jan 27
ORD
Chicago
EYW
Key West
$303 Roundtrip, found 1 hour ago
$303
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, Jan 21 from Chicago to Key West, returning Tue, Jan 27, priced at $303 found 1 hour ago
JetBlue Airways
Thu, Dec 4 - Thu, Dec 11
ORD
Chicago
EYW
Key West
$519 Roundtrip, found 1 day ago
$519
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Dec 4 from Chicago to Key West, returning Thu, Dec 11, priced at $519 found 1 day ago

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

November is typically the cheapest month to fly

From $189 - $513 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 $494
EYW
Key West Intl.
CheapestClosest
Average driving time to city center8 min
Flights from $494
Flights from Chicago (ORD) to Key West (EYW)
Origin airport
O'Hare Intl.
Destination airport
Key West Intl.
Airlines serving
American Airlines, Delta, JetBlue Airways, Spirit Airlines, United
Roundtrip price
$181
Distance
1254 mi

Chicago to Key West Flights

The cheapest times to fly from Chicago to Key West

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Key West are during the month of January. You can find some of the cheapest flights from Chicago to Key West with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Key West

Sunday is one of the best days to book for cheap flights from Chicago to Key West: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Key West

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Key West in 2025. You can also book with separate airlines for your outbound and return journeys, from $91 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Key West flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Key West airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW) cost?
Get a cheap one-way flight from $91 or cheap return flight from $181 from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)?
Flying in January is a good way to save, as it's the cheapest month for flights between ORD and EYW. You'll often find the lowest prices during the off-season.
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 O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)?
The cheapest airline to offer flights between O'Hare Intl. Airport (ORD) and Key West Intl. Airport (EYW) can vary based on when you want to travel. American Airlines and United Airlines are just some of the choices offering competitive fares. Use Expedia's filters to compare airlines in one place and find the right ORD to EYW flight for your budget.
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.

Explore a world of travel with Expedia

*Available to One Key members.