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Cheap EYW to ORD Flights

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

Key West to Chicago route information

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

Chicago

$446.00

Cheap EYW to ORD Flights

  • Can I change the date of my flight?

    Yes, you can adjust your departure date. If you want to save some funds in doing so, the lowest-cost day to fly in October is Tuesday. You may be thinking you're missing out taking off a day earlier, but we think that you are just adding saving towards a future holiday.
  • How long does the average person stay in Chicago?

    Of course, you're not an average person, but if you were, you'd stay roughly four days.
  • How long is the flight from EYW to ORD?

    United Airlines can get you there in three hours and 29 minutes. So, if you were to leave Key West at 3:26 PM EDT, you would get to Chicago at 5:55 PM CDT. Giving you enough time to catch up on your reading before you land (don't forget, there is a one-hour time difference).
  • How long does it take to fly from Key West to Chicago?

    If you're able to take the direct flight (which is offered by United Airlines), you will be able to leave EYW at 3:26 PM EDT and get to ORD at 5:55 PM CDT (three hours and 29 minutes). Remember, there is a time change of one hour.
  • What is the cheapest day to fly to Chicago?

    Sep 21st has bookings (as of Sep 16th) as cheap as $282. That comes in 27% below the average price. Saving on booking fees gives you more cash in your pocket.
  • What is the cheapest airline flying from Key West to Chicago?

    Silver Airways is the leader in keeping prices down for their passengers over the next three months. Fares are being booked at just $269 and, when compared to the more expensive bookings of $878, it's a great bargain.
  • How much is a plane ticket to Chicago (ORD) from Key West (EYW)?

    They can range from $269 to $878. Booking far in advance can usually help you get the cheapest rate. Don't forget, the sooner you book, the better price you tend to get.

Key West to Chicago 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 Key West to Chicago 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 Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with EYW to ORD flights that won’t make your bank account wince. Ready to temporarily leave behind Key West 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 ORD 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.

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 Expedia.com 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.