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Cheap Flights from Chicago to Key West from $408

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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.

Tue, Apr 28 - Tue, May 5
MDW
Chicago
to
EYW
Key West
$408

roundtrip

found 3 days ago

Open MDW to EYW flights search result page
Sat, Oct 5 - Thu, Oct 10
MDW
Chicago
to
EYW
Key West
$413

roundtrip

found 23 hours ago

Open MDW to EYW flights search result page
Sat, Oct 5 - Thu, Oct 10
MDW
Chicago
to
EYW
Key West
$416

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Sat, Oct 26 - Wed, Oct 30
MDW
Chicago
to
EYW
Key West
$422

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Fri, Jan 24 - Tue, Jan 28
MDW
Chicago
to
EYW
Key West
$430

roundtrip

found 3 days ago

Open MDW to EYW flights search result page
Thu, Jun 4 - Sat, Jun 13
MDW
Chicago
to
EYW
Key West
$433

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Tue, Apr 14 - Sat, Apr 18
MDW
Chicago
to
EYW
Key West
$438

roundtrip

found 22 hours ago

Open MDW to EYW flights search result page
Wed, Oct 2 - Sun, Oct 6
MDW
Chicago
to
EYW
Key West
$440

roundtrip

found 18 hours ago

Open MDW to EYW flights search result page
Wed, Nov 6 - Sat, Nov 9
MDW
Chicago
to
EYW
Key West
$445

roundtrip

found 4 days ago

Open MDW to EYW flights search result page
Sat, Nov 2 - Tue, Nov 5
MDW
Chicago
to
EYW
Key West
$446

roundtrip

just found

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Tue, Oct 1 - Mon, Oct 7
MDW
Chicago
to
EYW
Key West
$450

roundtrip

found 19 hours ago

Open MDW to EYW flights search result page
Wed, Sep 25 - Sat, Sep 28
MDW
Chicago
to
EYW
Key West
$454

roundtrip

found 4 days ago

Open MDW to EYW flights search result page
Wed, Dec 18 - Mon, Dec 23
MDW
Chicago
to
EYW
Key West
$456

roundtrip

found 3 days ago

Open MDW to EYW flights search result page
Thu, Feb 6 - Sat, Feb 15
MDW
Chicago
to
EYW
Key West
$458

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Mon, Nov 18 - Thu, Nov 21
MDW
Chicago
to
EYW
Key West
$464

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just found

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Sat, Apr 18 - Fri, Apr 24
MDW
Chicago
to
EYW
Key West
$466

roundtrip

found 5 hours ago

Open MDW to EYW flights search result page
Fri, Sep 27 - Wed, Oct 2
MDW
Chicago
to
EYW
Key West
$467

roundtrip

found 6 days ago

Open MDW to EYW flights search result page
Fri, Dec 13 - Tue, Dec 17
MDW
Chicago
to
EYW
Key West
$468

roundtrip

found 3 days ago

Open MDW to EYW flights search result page
Sun, Apr 12 - Sat, Apr 18
MDW
Chicago
to
EYW
Key West
$470

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Sat, Nov 2 - Tue, Nov 5
MDW
Chicago
to
EYW
Key West
$471

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just found

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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

Chicago

ORD-O'Hare Intl.

$227.06

Top Routes from Chicago

Top Routes to Key West

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 Expedia.com, 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 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.