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Cheap MDW 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 Midway Intl.
Destination Airport Key West Intl.
Airlines Serving Delta
Flight Price $408
Distance 1,239 mi



Cheap MDW to EYW Flights

  • How much is a plane ticket to Key West (EYW) from Chicago (MDW)?

    Cost can range from $385 to $1,117, prices for MDW to EYW change less than the majority of routes in the United States. Prices tend to be lower the further out you book.
  • Which airline has the least delays from Chicago to Key West?

    The current leader is NetJets Aviation with a 100% on-time rate. Spend as little time in an airport as necessary by flying with NetJets Aviation. Hopefully, they keep that perfect record alive.
  • Can I change the date of my flight?

    Yes, you can switch your departure date. If you wish to save some funds in doing so, the cheapest day to fly in September is Monday. Having flexibility in your travel plans means you can save more, so be sure to plan ahead when possible.
  • What is the cheapest day to fly to Key West?

    As of Sep 2nd, the cheapest day to fly from Chicago to Key West is Sep 12th. Tickets are presently $385, 20% less than the average price for this route.
  • How much time do people spend in Key West?

    The average time spent sightseeing in Key West by travelers from Chicago is five days.
  • What is the cheapest airline flying from Chicago to Key West?

    Delta Air Lines is offering the best deal at $385. Better snatch it up fast because prices range all the way up to $1,117 over the next three months.
  • What airports do you fly into for Key West?

    Departing from Chicago Midway International Airport is not the only way to get to Key West International Airport. Try searching for flights from O'Hare International Airport (ORD). Over the next few months, flights from ORD to EYW are being booked 17% cheaper than flights from MDW to EYW. Being only 16 miles away, it's easily accessible for most.

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 MDW 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.

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.