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MDW - EYW

$216 Find cheap flights from Chicago Midway Airport to Key West

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Key West departing on 8/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Fri 6/21
Fri 6/28

Search hundreds of travel sites at once for deals on flights to Key West

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Key West, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Key West, as well as popular online travel agencies
In the last 7 days travelers have searched 43,423,329 times on KAYAK, and here is why:

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Cheap flight deals from Midway to Key West (MDW-EYW)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Key West that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
10:11 am - 5:09 pmMDW-EYW
5h 58m1 stop
6:05 pm - 9:47 pmEYW-MDW
4h 42m1 stop
$216Delta
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Sat, Aug 10 - Sat, Aug 17
1:05 pm - 7:36 pmMDW-EYW
5h 31m1 stop
7:00 am - 11:53 amEYW-MDW
5h 53m1 stop
$287Delta
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Wed, Aug 7 - Wed, Aug 21
10:11 am - 5:09 pmMDW-EYW
5h 58m1 stop
6:05 pm - 9:47 pmEYW-MDW
4h 42m1 stop
$327Delta
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Sat, Aug 10 - Mon, Aug 19
12:35 pm - 7:30 pmMDW-EYW
5h 55m1 stop
6:03 pm - 9:46 pmEYW-MDW
4h 43m1 stop
$358Delta
Find Deal
Fri, Jul 19 - Tue, Jul 23
11:01 am - 7:40 pmMDW-EYW
7h 39m1 stop
6:10 pm - 10:01 pmEYW-MDW
4h 51m1 stop
$378Delta
Find Deal
Sat, Jun 1 - Mon, Jun 3
10:11 am - 5:09 pmMDW-EYW
5h 58m1 stop
7:00 am - 11:58 amEYW-MDW
5h 58m1 stop
$417Delta
Find Deal
Fri, Sep 6 - Mon, Sep 9
6:00 am - 1:41 pmMDW-EYW
6h 41m1 stop
6:03 pm - 9:46 pmEYW-MDW
4h 43m1 stop
$438Delta
Find Deal
Sat, Jul 27 - Sat, Aug 3
12:45 pm - 7:40 pmMDW-EYW
5h 55m1 stop
7:25 am - 11:55 amEYW-MDW
5h 30m1 stop
$463Delta
Find Deal
Tue, Jun 18 - Tue, Jun 25
10:11 am - 5:09 pmMDW-EYW
5h 58m1 stop
6:05 pm - 9:47 pmEYW-MDW
4h 42m1 stop
$488Delta
Find Deal
Thu, Aug 8 - Mon, Aug 12
12:35 pm - 7:30 pmMDW-EYW
5h 55m1 stop
7:15 am - 11:44 amEYW-MDW
5h 29m1 stop
$498Delta
Find Deal
Fri, Aug 2 - Sun, Aug 4

Flights from Midway to Key West - Travel Insights & Trends

Get data-powered insights and trends into flights from Midway to Key West to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago Midway Airport to Key West?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Key West, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago Midway Airport to Key West is August, where tickets cost $310 on average. On the other hand, the most expensive months are March and December, where the average cost of tickets is $529 and $518 respectively.

How far in advance should I book a flight from Chicago Midway Airport to Key West?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to Key West, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to Key West, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 60 days before departure.

Good to know

Low season

July

High season

December

Cheapest flight

$216
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Chicago Midway Airport to Key West

When to book flights from Midway to Key West

Are your dates flexible? Find out the best times to travel from Midway to Key West based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Key West flights

  • What is the cheapest flight from Chicago Midway Airport to Key West?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Key West was $254 for a one-way ticket and $216 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Key West?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Key West?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago Midway Airport to Key West?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Key West.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Key West?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Key West.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Key West?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Key West from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Key West?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Key West with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and EYW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Key West?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Key West from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airline flying from Midway to Key West

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Key West. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Key West? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10585 reviews
8.2Boarding
8.6Crew
7.9Comfort
7.4Food
8.0Entertainment
Airline reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

6.0 GoodGary, May 2024MSP - TPA
Read more about Delta reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

They did a fine job. Can't wait to use Delta in the future.

Seat back monitors and outlets were dead and not working.

The experience was good and the flight departed on time and landed early

The flight was delayed but we got to our final destination.

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

Boarding super slow with people allowed to linger in aisles

Book cheap flights from Chicago to Key West

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Key West found on KAYAK in the last 72 hours.
10/26Sat
1 stopDelta
4h 28mMDW-EYW
$254
9/2Mon
1 stopDelta
6h 05mMDW-EYW
$279
10/25Fri
1 stopDelta
5h 28mMDW-EYW
$284
8/30Fri
1 stopDelta
5h 31mMDW-EYW
$289
10/26Sat
2 stopsDelta
8h 58mMDW-EYW
$640
10/14Mon
1 stopDelta
5h 28mMDW-EYW
$669
8/30Fri
2 stopsDelta
9h 01mMDW-EYW
$710
9/2Mon
2 stopsDelta
9h 01mMDW-EYW
$809
10/25Fri
2 stopsDelta
8h 58mMDW-EYW
$819
10/14Mon
2 stopsDelta
8h 58mMDW-EYW
$1,585

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Last minute flights from Midway to Key West

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Key West that are departing in the next 10 days.
5/23Thu
multi-stopDelta
5h 58mMDW-EYW
5/27Mon
multi-stopDelta
5h 47mEYW-MDW
$878
5/23Thu
multi-stopDelta
9h 08mMDW-EYW
5/27Mon
multi-stopDelta
5h 47mEYW-MDW
$1,369
5/23Thu
multi-stopDelta
8h 54mMDW-EYW
5/27Mon
multi-stopDelta
12h 02mEYW-MDW
$5,108

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Chicago Midway Airport - Key West Flights

Departure:

Chicago Midway Airport (undefined)United States

Destination:

Key West (EYW)United States

Return flight deals:

Key West - Chicago Midway Airport

Cabin classes: