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

February is typically the cheapest month to fly

From £126 - £299 per traveller.

Frequently asked questions

How much does a flight from Chicago, IL (ORD-O'Hare Intl.) to Key West, FL (EYW-Key West Intl.) cost?
You can find one-way and return flights from ORD to EYW with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when ORD to EYW ticket fares go up or down.
What is the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to Key West, FL (EYW-Key West Intl.)?
The cheapest months to fly from ORD to EYW are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Chicago, IL (ORD-O'Hare Intl.) to Key West, FL (EYW-Key West Intl.)?
You have 2 airlines offering direct flights from Chicago, IL (ORD-O'Hare Intl.) to Key West, FL (EYW-Key West Intl.). Here are the carriers:
  • United operates 14 direct flights from Chicago, IL (ORD-O'Hare Intl.) to Key West, FL (EYW-Key West Intl.) every week.
  • American Airlines operates 7 direct flights from Chicago, IL (ORD-O'Hare Intl.) to Key West, FL (EYW-Key West Intl.) every week.
How do I find cheap flights from Chicago, IL (ORD) to Key West, FL (EYW)?
To find a cheap flight from Chicago, IL (ORD) to Key West, FL (EYW), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Chicago, IL (ORD-O'Hare Intl.) to Key West, FL (EYW-Key West Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Key West, FL (EYW-Key West Intl.)?
The earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Key West, FL (EYW-Key West Intl.) typically departs around 12:00 AM local time. This service is operated by American Airlines and is seasonal, active in December. An early departure like this can help you make the most of your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Key West, FL (EYW-Key West Intl.)?
When flying from Chicago, IL (ORD-O'Hare Intl.) to Key West, FL (EYW-Key West Intl.), you'll cover a distance of approximately 2,018 kilometers. A nonstop flight typically takes around 3 hours 30 minutes. If you opt for a flight with one stop, your journey will usually be longer, taking about 5 hours. Flights with two or more stops generally take even more time, averaging around 9 hours 30 minutes. Keep in mind that actual flight times can vary due to factors like wind patterns and air traffic, so it's always a good idea to allow for some flexibility in your travel plans.
Can you fly business or first class from Chicago, IL (ORD) to Key West, FL (EYW)?
Select the "Business class" and "First class" filters when looking for Chicago, IL (ORD) to Key West, FL (EYW) flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Chicago, IL (ORD) to Key West, FL (EYW) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD) to Key West, FL (EYW) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Key West, FL (EYW) from Chicago, IL (ORD)?
If you're planning to travel to Key West from O'Hare Intl. (ORD), you can fly directly into Key West Intl. (EYW). Some flights may connect through major hubs like Logan Intl. (BOS), Nashville Intl. (BNA), or Raleigh - Durham Intl. (RDU) before reaching Key West. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Chicago, IL (ORD-O'Hare Intl.) to Key West, FL (EYW-Key West Intl.) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD-O'Hare Intl.) to Key West, FL (EYW-Key West Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (ORD-O'Hare Intl.) to Key West, FL (EYW-Key West Intl.) flight and hotel package?
Securing a Chicago, IL (ORD-O'Hare Intl.) to Key West, FL (EYW-Key West Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (ORD) to Key West, FL (EYW)?
If you booked your Chicago, IL (ORD) to Key West, FL (EYW) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Key West Intl.
Distance
2006 km
Average flight time
4 hours 21 mins

Book with confidence

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, 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.  

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

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