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Cheap flights from Midway (MDW) to Key West (EYW) from $149

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 7/17. 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
May 2 — May 91
From?
To?
Thu 5/2
Thu 5/9
1 adult, Economy
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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 27, 2024.

Popular in

February

Cheapest in

August

Round-trip from

$374

One-way from

$149
High demand for flights, 39% potential price rise
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Best time to find cheap flights, 53% potential price drop
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From Chicago Midway to Key West
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One-way flight from Chicago Midway to Key West
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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 18% 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 2,991,349 searches. Data last updated April 27, 2024.
Wed 9/46:00 amMDW - EYW
1 stop6h 05mDelta
Tue 9/1012:31 pmEYW - MDW
1 stop6h 28mDelta
Deal found 4/26$248
Tue 6/1812:45 pmMDW - EYW
1 stop5h 55mDelta
Thu 6/2712:39 pmEYW - MDW
1 stop6h 20mDelta
Deal found 4/26$277
Mon 8/191:05 pmMDW - EYW
1 stop5h 31mDelta
Sat 8/2412:31 pmEYW - MDW
1 stop5h 43mDelta
Deal found 4/26$293
Wed 8/211:05 pmMDW - EYW
1 stop5h 31mDelta
Thu 8/296:05 pmEYW - MDW
1 stop4h 42mDelta
Deal found 4/26$328
Sat 7/201:05 pmMDW - EYW
1 stop5h 35mDelta
Wed 7/2412:39 pmEYW - MDW
1 stop6h 20mDelta
Deal found 4/26$343
Fri 8/2310:11 amMDW - EYW
1 stop5h 58mDelta
Mon 8/266:05 pmEYW - MDW
1 stop4h 42mDelta
Deal found 4/26$363
Wed 8/2110:11 amMDW - EYW
1 stop5h 58mDelta
Thu 8/2912:31 pmEYW - MDW
1 stop6h 28mDelta
Deal found 4/27$378
Thu 8/810:11 amMDW - EYW
1 stop5h 58mDelta
Sat 8/106:05 pmEYW - MDW
1 stop4h 42mDelta
Deal found 4/26$388
Fri 8/301:05 pmMDW - EYW
1 stop5h 31mDelta
Mon 9/212:31 pmEYW - MDW
1 stop6h 28mDelta
Deal found 4/26$448

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 2,991,349 searches. Prices were last updated on April 27, 2024.
Wed 5/2912:42 pmMDW - EYW
1 stop5h 58mDelta
Sun 6/27:05 amEYW - MDW
1 stop5h 47mDelta
Deal found 4/27$463
Fri 4/2610:00 amMDW - EYW
1 stop6h 15mDelta
Tue 4/306:10 pmEYW - MDW
1 stop5h 04mDelta
Deal found 4/25$478
Fri 5/108:45 amMDW - EYW
1 stop7h 27mDelta
Sun 5/1211:43 amEYW - MDW
1 stop7h 15mDelta
Deal found 4/26$483
Mon 5/612:45 pmMDW - EYW
1 stop6h 04mDelta
Sat 5/116:10 pmEYW - MDW
1 stop4h 51mDelta
Deal found 4/26$528
Wed 5/158:45 amMDW - EYW
1 stop7h 27mDelta
Mon 5/206:10 pmEYW - MDW
1 stop4h 51mDelta
Deal found 4/27$553
Mon 5/276:00 amMDW - EYW
1 stop6h 00mDelta
Mon 6/36:10 pmEYW - MDW
1 stop4h 51mDelta
Deal found 4/27$558
Thu 5/168:45 amMDW - EYW
1 stop7h 27mDelta
Tue 5/216:10 pmEYW - MDW
1 stop4h 51mDelta
Deal found 4/26$598
Fri 4/2610:00 amMDW - EYW
1 stop6h 15mDelta
Sun 4/286:10 pmEYW - MDW
1 stop5h 04mDelta
Deal found 4/26$648
Sat 5/2511:01 amMDW - EYW
1 stop5h 11mDelta
Tue 5/286:10 pmEYW - MDW
1 stop4h 51mDelta
Deal found 4/26$668

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 2,991,349 searches. Data last updated April 27, 2024.
Wed 9/46:00 amMDW - EYW
1 stop6h 05mDelta
Tue 9/1012:31 pmEYW - MDW
1 stop6h 28mDelta
Deal found 4/26$248
Tue 6/1812:45 pmMDW - EYW
1 stop5h 55mDelta
Thu 6/2712:39 pmEYW - MDW
1 stop6h 20mDelta
Deal found 4/26$277
Mon 8/191:05 pmMDW - EYW
1 stop5h 31mDelta
Sat 8/2412:31 pmEYW - MDW
1 stop5h 43mDelta
Deal found 4/26$293
Wed 8/211:05 pmMDW - EYW
1 stop5h 31mDelta
Thu 8/296:05 pmEYW - MDW
1 stop4h 42mDelta
Deal found 4/26$328
Sat 7/201:05 pmMDW - EYW
1 stop5h 35mDelta
Wed 7/2412:39 pmEYW - MDW
1 stop6h 20mDelta
Deal found 4/26$343
Fri 8/2310:11 amMDW - EYW
1 stop5h 58mDelta
Mon 8/266:05 pmEYW - MDW
1 stop4h 42mDelta
Deal found 4/26$363
Wed 8/2110:11 amMDW - EYW
1 stop5h 58mDelta
Thu 8/2912:31 pmEYW - MDW
1 stop6h 28mDelta
Deal found 4/27$378
Thu 8/810:11 amMDW - EYW
1 stop5h 58mDelta
Sat 8/106:05 pmEYW - MDW
1 stop4h 42mDelta
Deal found 4/26$388
Fri 8/301:05 pmMDW - EYW
1 stop5h 31mDelta
Mon 9/212:31 pmEYW - MDW
1 stop6h 28mDelta
Deal found 4/26$448

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 2,991,349 searches. Data last updated April 27, 2024.
Mon 5/612:45 pmMDW - EYW
1 stop6h 04mDelta
Sat 5/116:10 pmEYW - MDW
1 stop4h 51mDelta
Deal found 4/26$528
Mon 5/612:45 pmMDW - EYW
1 stop6h 04mDelta
Thu 5/91:55 pmEYW - MDW
1 stop5h 03mDelta
Deal found 4/26$838
Mon 5/66:00 amMDW - EYW
1 stop6h 00mDelta
Sat 5/117:05 amEYW - MDW
2 stops10h 50mDelta
Deal found 4/26$864
Thu 5/210:00 amMDW - EYW
1 stop6h 15mDelta
Mon 5/67:45 amEYW - MDW
1 stop5h 10mDelta
Deal found 4/26$1,018
Thu 5/26:30 amMDW - EYW
2 stops9h 45mDelta
Mon 5/67:45 amEYW - MDW
1 stop5h 10mDelta
Deal found 4/26$1,499
Mon 5/69:30 amMDW - EYW
2 stops9h 19mDelta
Thu 5/97:05 amEYW - MDW
1 stop5h 47mDelta
Deal found 4/26$1,915
Mon 5/69:30 amMDW - EYW
2 stops9h 19mDelta
Sat 5/117:05 amEYW - MDW
2 stops10h 08mDelta
Deal found 4/26$2,532
Thu 5/29:30 amMDW - EYW
2 stops9h 15mDelta
Mon 5/67:45 amEYW - MDW
2 stops9h 38mDelta
Deal found 4/26$2,974

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 2,991,349 searches. Data last updated April 27, 2024.
Wed 7/171:05 pmMDW - EYW
1 stop5h 35mDelta
Deal found 4/26$149
Sat 6/2210:41 amMDW - EYW
1 stop5h 24mDelta
Deal found 4/26$254
Mon 9/26:00 amMDW - EYW
1 stop6h 05mDelta
Deal found 4/26$279
Fri 8/3010:11 amMDW - EYW
1 stop5h 58mDelta
Deal found 4/26$289
Thu 6/612:42 pmMDW - EYW
1 stop5h 58mDelta
Deal found 4/26$369
Fri 5/248:45 amMDW - EYW
1 stop7h 27mDelta
Deal found 4/26$409
Fri 5/312:45 pmMDW - EYW
1 stop6h 00mDelta
Deal found 4/26$419
Thu 5/212:45 pmMDW - EYW
1 stop6h 00mDelta
Deal found 4/26$514
Sat 6/229:28 amMDW - EYW
2 stops9h 12mDelta
Deal found 4/26$600

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 2,991,349 searches. Data last updated April 27, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$248 - $448

Route

Depart

Return

Price

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 9/4

1 stop6h 05m

Key West

Tue 9/10

1 stop6h 28m

$248

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 6/18

1 stop5h 55m

Key West

Thu 6/27

1 stop6h 20m

$277

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Mon 8/19

1 stop5h 31m

Key West

Sat 8/24

1 stop5h 43m

$293

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 8/21

1 stop5h 31m

Key West

Thu 8/29

1 stop4h 42m

$328

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Sat 7/20

1 stop5h 35m

Key West

Wed 7/24

1 stop6h 20m

$343

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 8/23

1 stop5h 58m

Key West

Mon 8/26

1 stop4h 42m

$363

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 8/21

1 stop5h 58m

Key West

Thu 8/29

1 stop6h 28m

$378

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Thu 8/8

1 stop5h 58m

Key West

Sat 8/10

1 stop4h 42m

$388

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 8/30

1 stop5h 31m

Key West

Mon 9/2

1 stop6h 28m

$448

Flights are sorted by cheapest first

Deals found on 4/26

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 21, 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 $365 while a round-trip flight costs $341. Price data was last updated on April 21, 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

$487

July

$462

August

$384

September

$408

October

$468

November

$448

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 27, 2024.
Delta
8.1
Very good
10,951 reviews
Check prices

Boarding

8.2

Crew

8.6

Overall

8.1

Entertainment

8.0

Food

7.4

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.

Delta
8.1
Very good
10,951 reviews
Delta
8.1
Very good
10,951 reviews
Check prices

Boarding

8.2

Crew

8.6

Overall

8.1

Entertainment

8.0

Food

7.4

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 $248, but on average you can expect to pay $459.

  • Are there last-minute flights available from Chicago Midway Airport to Key West for under $600?

    There are currently 8+ open flights from Chicago Midway Airport to Key West within the next 7 days for less than $600.

  • 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 $248. Users have found that Delta is 60% 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 on your Midway to Key West flight 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 Midway to Key West 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 find direct flights from Midway to Key West.

  • 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 flying from Midway to Key West 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 4/27.

See more FAQs

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Alternative routes for Midway to Key West
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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 2,991,349 searches. Data last updated April 27, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$282Average$547FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
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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.
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Business Class
Prem Econ Class
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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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