£124 Cheap Flights from Chicago (ORD) to Key West (EYW)

View £124 flight on Mon, 8 Sep 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at £124 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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

November is typically the cheapest month to fly

From £141 - £493 per traveller.

Graph displaying average flight prices per month

Flight from Chicago to Key West route information
Origin airport
O'Hare Intl.
Destination airport
Key West Intl.
Return price
£410
Distance
2006 km
Average flight time
3 hours 11 mins

Compare flights from Chicago to Key West easily and book with confidence

For travelling on business or for pleasure, Expedia makes it easy to book your flights from Chicago to Key West. Operating between them flights per day, 20 airlines cover the route. And fly direct, getting you to Key West Intl. in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from O'Hare Intl. to Key West Intl..  

To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. 

Grab a great deal on your flight from O'Hare Intl. (ORD) to Key West Intl. (EYW)

The easiest way to view the best deals on flights from Chicago to Key West today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from O'Hare Intl. to Key West Intl. start at just and range up to .  

To find an even better deal, try  

  • being flexible on your dates – midweek flights can be cheaper
  • looking for other airports near Chicago and Key West
  • booking your flight during , the cheapest month on this route
  • varying your flight times – early morning and late at night are sometimes cheaper 

Why you should book your Chicago to Key West flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from O'Hare Intl. to Key West Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.  

Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.  

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 . 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 kilometres. Put together a playlist of your favourite 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 travellers, 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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