Beginning of main content
Round Trip Icon
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search over 1,000,000 properties worldwide and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheap ORD to EYW Flights

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Chicago to Key West route information

Origin Airport O'Hare Intl.
Destination Airport Key West Intl.
Airlines Serving American Airlines, Delta, JetBlue Airways, United
Flight Price $249
Distance 1,254 mi



Cheap ORD to EYW Flights

  • Which airline has the least delays from Chicago to Key West?

    Booking with Envoy Air means you will arrive to Key West approximately the time you were supposed to. In fact, this timely airline has a 90% on-time average.
  • How long is the flight from ORD to EYW?

    If you're able to take the direct flight (which is offered by United Airlines), you will be able to leave ORD at 10:40 AM CDT and get to EYW at 2:50 PM EDT (three hours and 10 minutes). Remember, there is a time change of one hour.
  • How many flights are there per day from Chicago to Key West?

    The number does differ by the day of the week, but on average, you can expect only one flight time when you book. The average route departing the United States currently has nine different flight times per day, so expect fewer options than you're used to.
  • Can I change the date of my flight?

    Yes, you can switch your departure date. If you want to save a little cash in doing so, the cheapest day to fly in October is Tuesday. Being flexible with your travel days can provide you extra savings when booking.
  • How long does it take to fly from Chicago to Key West?

    This flight takes around three hours and 10 minutes via United Airlines (don't forget, there is a time difference of one hour).
  • What is the cheapest airline flying from Chicago to Key West?

    JetBlue Airways is offering the best deal at $244. Better snatch it up quickly because prices range all the way up to $1,949 over the next three months.
  • How much is a plane ticket to Key West (EYW) from Chicago (ORD)?

    Cost can range from $244 to $1,949, prices for ORD to EYW fluctuate less than the majority of routes in the United States. However, usually the sooner you book, the better price you get.

Chicago to Key West Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Chicago to Key West will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Key West.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at, we’ll pair you up with ORD to EYW flights that won’t make your bank account wince. Ready to temporarily leave behind Chicago for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to EYW with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Jun 12, 2018

Everything a cetcthey kept us on plane in return flight one hour while they waited for an attendant to arrive from another plane . Should have left us in the airport until ready for us

May 10, 2018

Smoothest landing I've ever had in Key West airport

Mar 2, 2018

Need more legroom. Person in front of me was almost in my lap.

Feb 17, 2018

Good job

Jan 28, 2018

Direct to Key West was the best no changing planes

Feb 12, 2017

Nice direct flight

Package Disclaimer

*Savings amount equal to 100% when flight + hotel are booked together. Prices based on searches conducted by fellow shoppers within the past 24 hours. There is no guarantee that these prices will be in effect at the time of your search. Vacation package savings are based on comparison to prices on of the same components booked separately. Savings vary based on origin/destination, length of trip, stay dates and travel partners, and aren't available on all packages.