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$259+ Cheap flights from Key West (EYW) to Midway (MDW)

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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MDW
Jul 30 — Aug 61
From?
To?
Tue 7/30
Tue 8/6
1 adult, Economy
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What is the cheapest month to fly from Key West to Chicago Midway Airport?

October is one of the best times of the year to fly to Chicago Midway Airport from Key West. Prices for October average $370 per person but you can even find prices for as low as $223. The most expensive prices can be found in the month of November. Opting for a October flight can save you 39% on your journey compared to booking in November

What is the cheapest time of day to fly from EYW to MDW?

When flying from Key West to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap Key West to Midway flights in July & August 2024

Find cheap flight options from Key West to Midway specifically for the months of July and August 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,752,877 searches. Prices were last updated on July 25, 2024.
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/236:03 pmEYW - MDW
1 stop4h 43mDelta
Mon 8/266:11 amMDW - EYW
1 stop6h 24mDelta
Deal found 7/25$358
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2212:48 pmEYW - MDW
1 stop6h 17mDelta
Thu 8/2912:35 pmMDW - EYW
1 stop6h 03mDelta
Deal found 7/25$448
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/236:03 pmEYW - MDW
1 stop4h 43mDelta
Thu 8/296:11 amMDW - EYW
1 stop6h 24mDelta
Deal found 7/25$528
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/37:23 amEYW - MDW
1 stop5h 21mDelta
Sun 8/412:35 pmMDW - EYW
1 stop6h 03mDelta
Deal found 7/25$693
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2212:48 pmEYW - MDW
1 stop6h 17mDelta
Thu 8/299:32 amMDW - EYW
2 stops9h 06mDelta
Deal found 7/25$736
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/236:03 pmEYW - MDW
1 stop4h 43mDelta
Thu 8/299:32 amMDW - EYW
2 stops9h 06mDelta
Deal found 7/25$816
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/37:23 amEYW - MDW
1 stop5h 21mDelta
Sun 8/49:33 amMDW - EYW
2 stops9h 05mDelta
Deal found 7/25$904
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/236:03 pmEYW - MDW
1 stop4h 43mDelta
Mon 8/269:25 amMDW - EYW
2 stops9h 13mDelta
Deal found 7/25$966
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/37:23 amEYW - MDW
2 stops10h 40mDelta
Sun 8/49:33 amMDW - EYW
2 stops9h 05mDelta
Deal found 7/25$1,985

Key West to Midway 2024 flight deals

Discover exclusive flight deals for travel between Key West and Midway in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,752,877 searches. Data last updated July 25, 2024.
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/236:03 pmEYW - MDW
1 stop4h 43mDelta
Mon 8/266:11 amMDW - EYW
1 stop6h 24mDelta
Deal found 7/25$358
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2212:48 pmEYW - MDW
1 stop6h 17mDelta
Thu 8/2912:35 pmMDW - EYW
1 stop6h 03mDelta
Deal found 7/25$448
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/236:03 pmEYW - MDW
1 stop4h 43mDelta
Thu 8/296:11 amMDW - EYW
1 stop6h 24mDelta
Deal found 7/25$528
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/37:23 amEYW - MDW
1 stop5h 21mDelta
Sun 8/412:35 pmMDW - EYW
1 stop6h 03mDelta
Deal found 7/25$693
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2212:48 pmEYW - MDW
1 stop6h 17mDelta
Thu 8/299:32 amMDW - EYW
2 stops9h 06mDelta
Deal found 7/25$736
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/236:03 pmEYW - MDW
1 stop4h 43mDelta
Thu 8/299:32 amMDW - EYW
2 stops9h 06mDelta
Deal found 7/25$816
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/37:23 amEYW - MDW
1 stop5h 21mDelta
Sun 8/49:33 amMDW - EYW
2 stops9h 05mDelta
Deal found 7/25$904
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/236:03 pmEYW - MDW
1 stop4h 43mDelta
Mon 8/269:25 amMDW - EYW
2 stops9h 13mDelta
Deal found 7/25$966
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/37:23 amEYW - MDW
2 stops10h 40mDelta
Sun 8/49:33 amMDW - EYW
2 stops9h 05mDelta
Deal found 7/25$1,985

Key West to Midway flights leaving soon

Find last-minute flight options from Key West to Midway 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 2,752,877 searches. Data last updated July 25, 2024.
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/37:23 amEYW - MDW
1 stop5h 21mDelta
Sun 8/412:35 pmMDW - EYW
1 stop6h 03mDelta
Deal found 7/25$693
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/37:23 amEYW - MDW
1 stop5h 21mDelta
Sun 8/49:33 amMDW - EYW
2 stops9h 05mDelta
Deal found 7/25$904
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/37:23 amEYW - MDW
2 stops10h 40mDelta
Sun 8/49:33 amMDW - EYW
2 stops9h 05mDelta
Deal found 7/25$1,985

One-way flights to Midway from Key West

Search for one-way flight options from Key West to Midway. 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 2,752,877 searches. Data last updated July 25, 2024.
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/236:03 pmEYW - MDW
1 stop4h 43mDelta
Deal found 7/25$259
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/47:23 amEYW - MDW
1 stop5h 21mDelta
Deal found 7/25$424
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/3112:42 pmEYW - MDW
1 stop6h 23mDelta
Deal found 7/25$519
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/36:03 pmEYW - MDW
1 stop5h 01mDelta
Deal found 7/25$549
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/247:23 amEYW - MDW
2 stops10h 41mDelta
Deal found 7/25$567
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/237:23 amEYW - MDW
2 stops12h 15mDelta
Deal found 7/25$718
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/37:38 amEYW - MDW
2 stops9h 49mDelta
Deal found 7/25$837
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/317:23 amEYW - MDW
2 stops12h 16mDelta
Deal found 7/25$981
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/47:23 amEYW - MDW
2 stops7h 46mDelta
Deal found 7/25$1,188

Find flights from Key West to Midway within your budget

Customize your flight search to find flights from Key West to Midway 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 2,752,877 searches. Data last updated July 25, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$358 - $966

Route

Depart

Return

Price

Key WestChicago Midway

EYW - MDW

EYWMDW

Key West

Fri 8/23

1 stop4h 43m

Chicago Midway

Mon 8/26

1 stop6h 24m

$358

Key WestChicago Midway

EYW - MDW

EYWMDW

Key West

Thu 8/22

1 stop6h 17m

Chicago Midway

Thu 8/29

1 stop6h 03m

$448

Key WestChicago Midway

EYW - MDW

EYWMDW

Key West

Fri 8/23

1 stop4h 43m

Chicago Midway

Thu 8/29

1 stop6h 24m

$528

Key WestChicago Midway

EYW - MDW

EYWMDW

Key West

Thu 8/22

1 stop6h 17m

Chicago Midway

Thu 8/29

2 stops9h 06m

$736

Key WestChicago Midway

EYW - MDW

EYWMDW

Key West

Fri 8/23

1 stop4h 43m

Chicago Midway

Thu 8/29

2 stops9h 06m

$816

Key WestChicago Midway

EYW - MDW

EYWMDW

Key West

Fri 8/23

1 stop4h 43m

Chicago Midway

Mon 8/26

2 stops9h 13m

$966

Flights are sorted by cheapest first

Deals found on 7/25

No data available for this route at this time. Please check back soon.

Best time to book a flight from Key West to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Key West with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated July 25, 2024.
Delta
8.0
Very good
9,630 reviews

Entertainment

8.0

Overall

8.0

Food

7.4

Comfort

7.9

Boarding

8.2

Crew

8.6

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Delta
8.0
Very good
9,630 reviews
Delta
8.0
Very good
9,630 reviews

Entertainment

8.0

Overall

8.0

Food

7.4

Comfort

7.9

Boarding

8.2

Crew

8.6

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Related info for your journey

Find useful and relevant information for your journey from Key West to Midway. 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 from for flights from Key West to Chicago Midway?

    If you book a flight to Chicago Midway from Key West, you will be flying from Key West, which is the city’s only airport. Key West (EYW) is located 2.6 mi from the center of Key West. There are 0 flights from Key West to Chicago Midway per day from 0 different airlines.

  • Can I find flights from Key West to Chicago Midway Airport for under $400 on Cheapflights?

    Yes, there are multiple flights from Key West to Chicago Midway Airport for under $400. The cheapest flight booked recently is on Delta for just $358, but on average you can expect to pay $642.

  • Are there last-minute flights available from Key West to Chicago Midway Airport for under $700?

    There are currently 3+ open flights from Key West to Chicago Midway Airport within the next 7 days for less than $700.

  • What does EYW to MDW mean?

    These are just IATA (International Air Transport Association) codes. They are used in aviation to identify and differentiate airports. That’s why a Key West Airport to Chicago Midway Airport flight would often be abbreviated as a EYW to MDW flight.

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

    The amount of baggage you can bring on your Key West to Midway 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 Key West to Midway with specific airlines?

    Yes, Cheapflights allows you to browse and filter Key West to Midway 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 Key West to Midway that include hotel bookings?

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

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

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Key West to Midway.

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

    Yes. Cheapflights offers flight deals from Key West to Midway 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 Key West to Midway that allow pets onboard?

    Many airlines flying from Key West to Midway 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 Key West to Midway?

    Yes, you can often find last-minute deals on Key West to Midway 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 Key West to Chicago Midway Airport flight deals updated?

    The Key West to Chicago Midway Airport flight deals you see on this page were last updated on 7/25.

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

    Currently, September is the cheapest month in which you can book a flight from Key West to Chicago Midway Airport (average of $137). Flying from Key West to Chicago Midway Airport in July is currently the most expensive (average of $231). 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.

See more FAQs

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Alternative routes for Key West to Midway
See prices for flight routes from nearby airports that may be better suited for you.

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Search flights from Key West to Midway by cabin class

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