CA $227 Cheap Flights from Chicago (ORD) to Key West (EYW)

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 CA $227 for one-way flights and CA $397 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Delta
Delta
Delta
Delta
Delta
Delta
Delta
American Airlines
United

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

November is typically the cheapest month to fly

From CA $260 - CA $908 per traveller.

Graph displaying average flight prices per month

Flight from Chicago to Key West (ORD - EYW) route information
Origin airport
O'Hare Intl.
Destination airport
Key West Intl.
Airlines serving
American Airlines, Delta, United
Roundtrip price
CA $397
Distance
2006 km
Average flight time
3 hours 11 mins

Chicago to Key West Flights

The easy way to book your flights from Chicago to Key West 

With Expedia, it’s simple to find and book flights to Key West from Chicago whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to Key West Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Chicago to Key West today, tomorrow, or this week.  

 

Save dollars with cheap flights from O'Hare Intl., ORD to Key West Intl., EYW 

Sort your search results by price to find great deals on your flight from Chicago to Key West—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Key West from Chicago currently is just CA $397 rising to CA $750.  

Here are more money-saving tips: 

  • Fly in August when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Key West  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Key West from Chicago 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Key West with Expedia today.

Frequently asked questions

How much is a flight from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)?
Based on airfares available within the last 7 days on Expedia for flights departing within the next year, round-trip journeys from O'Hare Airport to Key West Intl. Airport (EYW) start from CA $397. Make your booking ASAP to get the best price for your big adventure. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from ORD to EYW?
Each air carrier has its own terms and conditions. If you do decide to cancel, follow the easy instructions on our Customer Service Portal.
How do I find cheap flights from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW) that have flexible change policies?
Flights from ORD to Key West Intl. Airport offering flexible change policies are available with many carriers. Simply use our "No change fees" filter while searching. You'll only need to pay the cost difference between the two flights, without any additional fees to worry about.
How many hours is the flight from O'Hare Airport to Key West Intl. Airport?
Consider bringing your own on-board entertainment (like some downloaded podcasts), as it takes roughly 5 hours and 21 minutes to jet to EYW from O'Hare Airport. A set of noise-cancelling headphones will also be useful.
How far is the flight from ORD to Key West Intl. Airport (EYW)?
It's around 2,000 kilometres between O'Hare Airport and Key West Intl. Airport, so you'll be up in the air for a while. Keep yourself entertained by packing things like crossword puzzles or a good old-fashioned book.
Which airlines fly direct from O'Hare Airport to Key West Intl. Airport (EYW)?
A popular airline that flies from O'Hare Airport to Key West Intl. Airport (EYW) is American Airlines (AA). It offers 30 monthly flights. You could also check out the airfares with United Airlines (UA). This carrier operates 30 flights a month between Chicago and Key West.
Are ORD to EYW flight tickets cheaper when they're purchased at the last minute?
Flight prices fluctuate, so not always. While last-minute deals between O'Hare Airport and EYW are of course possible, it also makes sense to keep a close eye on prices well before you fly. In fact, some airlines publish their prices up to a year prior to the departure date. Expedia is constantly updating the biggest bargains around, so keep checking and be ready to grab your seat when the price dips.

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