Cheap flights from Midway (MDW) to Key West (EYW) from $98

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/14. 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.
MDW — EYW
Apr 21 — Apr 281

Cheap flight deals from Midway to Key West

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Key West (EYW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 16, 2024.

Popular in

February

Cheapest in

August

Round-trip from

$374

One-way from

$98
High demand for flights, 39% potential price rise
Best time to find cheap flights, 53% potential price drop
From Chicago Midway to Key West
One-way flight from Chicago Midway to Key West

What is the cheapest day to fly round-trip from Chicago Midway Airport to Key West?

It’s generally more expensive to depart on a Tuesday, if you have to leave on this day you can still search on Cheapflights to find great options that meet your needs.

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

To save on the cost of your flight from Chicago Midway Airport to Key West, book at least 26 days before your planned departure. Booking around this time can save you about 75% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $355 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $606.

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

August is one of the best times of the year to fly to Key West from Chicago Midway Airport. Prices for August average $462 per person but you can even find prices for as low as $226. The most expensive prices can be found in the month of March. Opting for a August flight can save you 29% on your journey compared to booking in March

When is the cheapest time to fly from Chicago Midway Airport to Key West (MDW - EYW)?

When flying from Chicago Midway Airport to Key West, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 20% versus a flight at noon.

Cheap Delta flights from Midway to Key West

Explore cheap flight options specifically provided by Delta for the route between Midway and Key West. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 3,185,007 searches. Data last updated April 16, 2024.
Tue 5/286:00 amMDW - EYW
1 stop6h 00mDelta
Thu 6/66:10 pmEYW - MDW
1 stop4h 51mDelta
Deal found 4/14$277
Tue 5/286:00 amMDW - EYW
1 stop6h 00mDelta
Tue 6/46:10 pmEYW - MDW
1 stop4h 51mDelta
Deal found 4/16$282
Fri 9/610:11 amMDW - EYW
1 stop5h 58mDelta
Tue 9/1012:31 pmEYW - MDW
1 stop6h 28mDelta
Deal found 4/16$298
Tue 8/61:05 pmMDW - EYW
1 stop5h 31mDelta
Fri 8/1612:31 pmEYW - MDW
1 stop6h 28mDelta
Deal found 4/15$313
Tue 5/1412:42 pmMDW - EYW
1 stop5h 58mDelta
Tue 5/216:10 pmEYW - MDW
1 stop4h 51mDelta
Deal found 4/16$327
Wed 8/2110:11 amMDW - EYW
1 stop5h 58mDelta
Thu 8/296:05 pmEYW - MDW
1 stop4h 42mDelta
Deal found 4/15$338
Tue 5/286:00 amMDW - EYW
1 stop6h 00mDelta
Wed 6/56:10 pmEYW - MDW
1 stop14h 45mDelta
Deal found 4/14$341
Fri 4/266:00 amMDW - EYW
1 stop6h 00mDelta
Wed 5/14:11 pmEYW - MDW
1 stop7h 03mDelta
Deal found 4/16$343
Tue 8/61:05 pmMDW - EYW
1 stop5h 31mDelta
Tue 8/137:00 amEYW - MDW
1 stop11h 59mDelta
Deal found 4/15$357

Cheap Midway to Key West flights in April & May 2024

Find cheap flight options from Midway to Key West specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,185,007 searches. Prices were last updated on April 16, 2024.
Tue 5/286:00 amMDW - EYW
1 stop6h 00mDelta
Thu 6/66:10 pmEYW - MDW
1 stop4h 51mDelta
Deal found 4/14$277
Tue 5/286:00 amMDW - EYW
1 stop6h 00mDelta
Tue 6/46:10 pmEYW - MDW
1 stop4h 51mDelta
Deal found 4/16$282
Tue 5/286:00 amMDW - EYW
1 stop6h 00mDelta
Wed 6/56:10 pmEYW - MDW
1 stop14h 45mDelta
Deal found 4/14$341
Thu 5/307:49 amMDW - EYW
1 stop10h 46mMultiple Airlines
Tue 6/410:35 amEYW - MDW
2 stops11h 56mMultiple Airlines
Deal found 4/14$348
Fri 5/3112:42 pmMDW - EYW
1 stop5h 58mDelta
Tue 6/46:10 pmEYW - MDW
1 stop4h 51mDelta
Deal found 4/14$358
Tue 5/286:00 amMDW - EYW
1 stop6h 00mDelta
Sun 6/27:05 amEYW - MDW
1 stop15h 56mDelta
Deal found 4/14$361
Tue 4/2312:45 pmMDW - EYW
1 stop6h 00mDelta
Sat 4/276:10 pmEYW - MDW
1 stop5h 04mDelta
Deal found 4/15$378
Mon 5/66:55 amMDW - EYW
2 stops11h 40mMultiple Airlines
Sun 5/123:21 pmEYW - MDW
1 stop19h 26mMultiple Airlines
Deal found 4/15$384
Tue 4/236:00 amMDW - EYW
1 stop6h 00mDelta
Sat 4/276:10 pmEYW - MDW
1 stop5h 04mDelta
Deal found 4/16$388

Midway to Key West 2024 flight deals

Discover exclusive flight deals for travel between Midway and Key West in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,185,007 searches. Data last updated April 16, 2024.
Tue 5/286:00 amMDW - EYW
1 stop6h 00mDelta
Thu 6/66:10 pmEYW - MDW
1 stop4h 51mDelta
Deal found 4/14$277
Tue 5/286:00 amMDW - EYW
1 stop6h 00mDelta
Tue 6/46:10 pmEYW - MDW
1 stop4h 51mDelta
Deal found 4/16$282
Sun 7/142:45 pmMDW - EYW
1 stop17h 16mMultiple Airlines
Thu 7/183:05 pmEYW - MDW
1 stop6h 54mMultiple Airlines
Deal found 4/14$289
Tue 8/61:05 pmMDW - EYW
1 stop5h 31mDelta
Wed 8/147:00 amEYW - MDW
1 stop5h 53mDelta
Deal found 4/15$313
Wed 8/2110:11 amMDW - EYW
1 stop5h 58mDelta
Thu 8/296:05 pmEYW - MDW
1 stop4h 42mDelta
Deal found 4/15$338
Tue 5/286:00 amMDW - EYW
1 stop6h 00mDelta
Wed 6/56:10 pmEYW - MDW
1 stop14h 45mDelta
Deal found 4/14$341
Thu 5/307:49 amMDW - EYW
1 stop10h 46mMultiple Airlines
Tue 6/410:35 amEYW - MDW
2 stops11h 56mMultiple Airlines
Deal found 4/14$348
Tue 8/61:05 pmMDW - EYW
1 stop5h 31mDelta
Tue 8/137:00 amEYW - MDW
1 stop11h 59mDelta
Deal found 4/15$357
Fri 5/3112:42 pmMDW - EYW
1 stop5h 58mDelta
Thu 6/66:10 pmEYW - MDW
1 stop4h 51mDelta
Deal found 4/14$358

Midway to Key West flights leaving soon

Find last-minute flight options from Midway to Key West for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,185,007 searches. Data last updated April 16, 2024.
Tue 4/2312:45 pmMDW - EYW
1 stop6h 00mDelta
Sat 4/276:10 pmEYW - MDW
1 stop5h 04mDelta
Deal found 4/15$378
Tue 4/236:00 amMDW - EYW
1 stop6h 00mDelta
Sat 4/276:10 pmEYW - MDW
1 stop5h 04mDelta
Deal found 4/16$388
Thu 4/2510:00 amMDW - EYW
1 stop6h 15mDelta
Tue 4/306:10 pmEYW - MDW
1 stop5h 04mDelta
Deal found 4/15$468
Fri 4/2610:37 amMDW - EYW
1 stop22h 48mMultiple Airlines
Sun 4/284:44 pmEYW - MDW
1 stop23h 30mMultiple Airlines
Deal found 4/15$476
Fri 4/264:04 pmMDW - EYW
2 stops45h 30mAllegiant Air
Sun 4/284:44 pmEYW - MDW
1 stop23h 30mAllegiant Air
Deal found 4/14$553
Fri 4/266:00 amMDW - EYW
1 stop6h 00mDelta
Mon 4/296:10 pmEYW - MDW
1 stop5h 04mDelta
Deal found 4/15$578
Fri 4/264:51 pmMDW - EYW
2 stops16h 34mMultiple Airlines
Sun 4/288:00 pmEYW - MDW
1 stop14h 47mMultiple Airlines
Deal found 4/15$598
Wed 4/246:00 amMDW - EYW
1 stop6h 00mDelta
Sun 4/287:45 amEYW - MDW
1 stop5h 10mDelta
Deal found 4/15$698
Thu 4/2510:00 amMDW - EYW
1 stop6h 15mDelta
Sun 4/287:45 amEYW - MDW
1 stop5h 10mDelta
Deal found 4/16$768

One-way flights to Key West from Midway

Search for one-way flight options from Midway to Key West. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,185,007 searches. Data last updated April 16, 2024.
Tue 5/148:45 amMDW - EYW
1 stop7h 27mDelta
Deal found 4/15$98
Tue 7/161:05 pmMDW - EYW
1 stop5h 35mDelta
Deal found 4/15$129
Tue 7/2312:34 pmMDW - EYW
1 stop27h 01mMultiple Airlines
Deal found 4/15$156
Wed 7/2412:34 pmMDW - EYW
1 stop19h 41mMultiple Airlines
Deal found 4/15$162
Wed 7/1710:11 amMDW - EYW
1 stop5h 54mDelta
Deal found 4/15$179
Tue 7/239:44 pmMDW - EYW
2 stops12h 01mMultiple Airlines
Deal found 4/15$220
Sun 5/198:45 amMDW - EYW
1 stop7h 27mDelta
Deal found 4/15$254
Tue 10/810:11 amMDW - EYW
1 stop5h 58mDelta
Deal found 4/16$259
Wed 7/243:28 pmMDW - EYW
2 stops16h 47mMultiple Airlines
Deal found 4/15$263

Find flights from Midway to Key West within your budget

Customize your flight search to find flights from Midway to Key West that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 3,185,007 searches. Data last updated April 16, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$277 - $553

Route

Depart

Return

Price

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 5/28

1 stop6h 00m

Key West

Thu 6/6

1 stop4h 51m

$277

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 5/28

1 stop6h 00m

Key West

Tue 6/4

1 stop4h 51m

$282

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Sun 7/14

1 stop17h 16m

Key West

Thu 7/18

1 stop6h 54m

$289

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 9/6

1 stop5h 58m

Key West

Tue 9/10

1 stop6h 28m

$298

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 8/6

1 stop5h 31m

Key West

Fri 8/16

1 stop6h 28m

$313

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 5/14

1 stop5h 58m

Key West

Tue 5/21

1 stop4h 51m

$327

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Thu 5/30

1 stop10h 46m

Key West

Tue 6/4

2 stops11h 56m

$348

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Mon 5/6

2 stops11h 40m

Key West

Sun 5/12

1 stop19h 26m

$384

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 4/26

2 stops45h 30m

Key West

Sun 4/28

1 stop23h 30m

$553

Flights are sorted by cheapest first

Deals found on 4/14

When is the cheapest time to fly from Chicago Midway Airport to Key West?

Use this chart to determine the cheapest time to fly round-trip from Midway to Key West. Price data was last updated on April 14, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Chicago Midway Airport to Key West flight should consider departing on Wednesday mornings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Average price of flights to Key West by month

Plan your trip from Midway to Key West by taking into account the cheapest months to travel. The average price of a one-way flight from Midway to Key West is currently $191 while a round-trip flight costs $341. Price data was last updated on April 14, 2024.

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Key West (average of $374). Flying from Chicago Midway Airport to Key West in March is currently the most expensive (average of $504). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

January

$374

February

$415

March

$504

April

$482

May

$475

June

$494

July

$465

August

$385

September

$413

October

$468

November

$450

December

$398

Temperature and rainfall in Key West by month

Plan your trip to Key West by taking into account the average temperature and rainfall totals by month.

EYW

Temperature

69.8 - 84.2 °F

Reviews of airlines servicing Key West

Get insights into the airlines that provide service to Key West. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Key West. Reviews last updated April 16, 2024.
8.1
Very good
11,123 reviews

Entertainment

8.0

Food

7.5

Crew

8.6

Overall

8.1

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

8.1
Very good
11,123 reviews
8.1
Very good
11,123 reviews

Entertainment

8.0

Food

7.5

Crew

8.6

Overall

8.1

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

7.5
Good
1,046 reviews
8.1
Very good
11,123 reviews

Entertainment

8.0

Food

7.5

Crew

8.6

Overall

8.1

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

Related info for your journey

Find useful and relevant information for your journey from Midway to Key West. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • What airport do you fly into for flights to Key West from Chicago Midway?

    Key West (EYW), located 2.6 mi from the city center, is the airport you fly into when you book flights from Chicago Midway to Key West. 1 airline have flights to Key West from Chicago Midway on a regular basis. Booking flights from Chicago Midway to Key West should not be difficult; the airport handles an average of 0 inbound flights from Chicago Midway per day.

  • Can I find flights from Chicago Midway Airport to Key West for under $300 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to Key West for under $300. The cheapest flight booked recently is on Delta for just $277, but on average you can expect to pay $344.

  • Are there last-minute flights available from Chicago Midway Airport to Key West for under $400?

    There are currently 20+ open flights from Chicago Midway Airport to Key West within the next 7 days for less than $400.

  • What is the cheapest airline to fly from Chicago Midway Airport to Key West round-trip?

    Flying on Delta is currently your cheapest option to Key West, with prices starting at $277. Users have found that Delta is 56% cheaper than the other options available to this destination.

  • What does MDW to EYW mean?

    MDW stands for Chicago Midway Airport, while EYW stands for Key West Airport. These codes are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry.

  • Can I find deals for flights from Midway to Key West that include extra baggage allowance?

    The amount of baggage you can bring depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Midway to Key West with specific airlines?

    Yes, Cheapflights allows you to browse and filter flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Midway to Key West that include hotel bookings?

    Yes. In addition to deals on Midway to Key West flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Key West?

    After entering your origin and destination, apply the non-stop filter on the search result page to see available direct flights.

  • Can I find deals for business class flights from Midway to Key West?

    Yes. Cheapflights offers flight deals from Midway to Key West by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Midway to Key West that allow pets onboard?

    Many airlines do offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Midway to Key West?

    Yes, you can often find last-minute deals on Midway to Key West flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago Midway Airport to Key West flight deals updated?

    The Chicago Midway Airport to Key West flight deals you see on this page were last updated on 4/16.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Midway to Key West

Discover the top airline that operate flights from Midway to Key West. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 3,185,007 searches. Data last updated April 16, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$273Average$546FlexibilityNo cancel feeOn-timeN/A
Search Delta flights

Search flights from Midway to Key West by cabin class

Find flights from Midway to Key West, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Midway to Key West?

Deals for Midway to Key West flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Midway to Key West?

Cheapflights helps you find that perfect flight to Key West from Midway by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Midway to Key West with no change fees?

Certainly. Search results for flights to Key West from Midway shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Midway to Key West become cheaper?

Of course! You can now track prices for flights from Midway to Key West and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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