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Cheap flights from Key West (EYW) to Midway (MDW) from $216

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/10. 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.
EYW — MDW
May 13 — May 201
From?
To?
Mon 5/13
Mon 5/20
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 $369 per person but you can even find prices for as low as $227. The most expensive prices can be found in the month of November. Opting for a October flight can save you 37% on your journey compared to booking in November

When is the cheapest time to fly from Key West to Chicago Midway Airport (EYW - 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 Delta flights from Key West to Midway

Explore cheap flight options specifically provided by Delta for the route between Key West and Midway. 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 2,749,864 searches. Data last updated May 8, 2024.
Tue 9/106:05 pmEYW - MDW
1 stop4h 39mDelta
Wed 9/181:05 pmMDW - EYW
1 stop5h 28mDelta
Deal found 5/6$216
Tue 9/106:05 pmEYW - MDW
1 stop4h 39mDelta
Mon 9/161:05 pmMDW - EYW
1 stop5h 28mDelta
Deal found 5/6$297
Mon 6/36:10 pmEYW - MDW
1 stop4h 51mDelta
Mon 6/1010:41 amMDW - EYW
1 stop5h 24mDelta
Deal found 5/6$313
Fri 9/136:05 pmEYW - MDW
1 stop4h 39mDelta
Wed 9/181:05 pmMDW - EYW
1 stop5h 28mDelta
Deal found 5/6$317
Thu 9/126:05 pmEYW - MDW
1 stop4h 39mDelta
Sun 9/156:00 amMDW - EYW
1 stop4h 48mDelta
Deal found 5/6$378
Fri 6/76:00 pmEYW - MDW
1 stop4h 46mDelta
Mon 6/106:00 amMDW - EYW
1 stop6h 20mDelta
Deal found 5/7$388
Tue 9/106:05 pmEYW - MDW
1 stop4h 39mDelta
Thu 9/1910:11 amMDW - EYW
1 stop8h 22mDelta
Deal found 5/6$396
Thu 5/166:10 pmEYW - MDW
1 stop4h 51mDelta
Thu 5/2312:42 pmMDW - EYW
1 stop5h 58mDelta
Deal found 5/6$428
Mon 8/266:05 pmEYW - MDW
1 stop4h 42mDelta
Sat 8/3110:11 amMDW - EYW
1 stop5h 58mDelta
Deal found 5/7$518

Cheap Key West to Midway flights in May & June 2024

Find cheap flight options from Key West to Midway specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,749,864 searches. Prices were last updated on May 8, 2024.
Mon 6/36:10 pmEYW - MDW
1 stop4h 51mDelta
Mon 6/1010:41 amMDW - EYW
1 stop5h 24mDelta
Deal found 5/6$313
Fri 6/76:00 pmEYW - MDW
1 stop4h 46mDelta
Mon 6/106:00 amMDW - EYW
1 stop6h 20mDelta
Deal found 5/7$388
Sat 5/116:10 pmEYW - MDW
1 stop4h 51mDelta
Tue 5/1412:42 pmMDW - EYW
1 stop5h 58mDelta
Deal found 5/5$428
Sat 5/116:10 pmEYW - MDW
1 stop4h 51mDelta
Tue 5/148:45 amMDW - EYW
1 stop7h 27mDelta
Deal found 5/6$438
Thu 5/96:10 pmEYW - MDW
1 stop4h 51mDelta
Sun 5/1212:42 pmMDW - EYW
1 stop5h 58mDelta
Deal found 5/6$478
Thu 5/911:43 amEYW - MDW
1 stop7h 15mDelta
Sun 5/126:00 amMDW - EYW
1 stop6h 00mDelta
Deal found 5/7$488
Sat 5/116:10 pmEYW - MDW
2 stops19h 30mDelta
Tue 5/1412:42 pmMDW - EYW
1 stop5h 58mDelta
Deal found 5/5$821
Sat 5/116:10 pmEYW - MDW
1 stop4h 51mDelta
Tue 5/141:21 pmMDW - EYW
2 stops29h 19mDelta
Deal found 5/6$826
Thu 6/207:25 amEYW - MDW
2 stops12h 11mDelta
Mon 6/2412:45 pmMDW - EYW
1 stop5h 55mDelta
Deal found 5/6$856

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 2,749,864 searches. Data last updated May 8, 2024.
Tue 9/106:05 pmEYW - MDW
1 stop4h 39mDelta
Tue 9/176:00 amMDW - EYW
1 stop4h 48mDelta
Deal found 5/6$216
Tue 9/106:05 pmEYW - MDW
1 stop4h 39mDelta
Mon 9/161:05 pmMDW - EYW
1 stop5h 28mDelta
Deal found 5/6$297
Mon 6/36:10 pmEYW - MDW
1 stop4h 51mDelta
Mon 6/1010:41 amMDW - EYW
1 stop5h 24mDelta
Deal found 5/6$313
Fri 9/136:05 pmEYW - MDW
1 stop4h 39mDelta
Tue 9/176:00 amMDW - EYW
1 stop6h 07mDelta
Deal found 5/6$317
Thu 9/126:05 pmEYW - MDW
1 stop4h 39mDelta
Sun 9/156:00 amMDW - EYW
1 stop4h 48mDelta
Deal found 5/6$378
Fri 6/76:00 pmEYW - MDW
1 stop4h 46mDelta
Mon 6/106:00 amMDW - EYW
1 stop6h 20mDelta
Deal found 5/7$388
Tue 9/106:05 pmEYW - MDW
1 stop4h 39mDelta
Thu 9/1910:11 amMDW - EYW
1 stop8h 22mDelta
Deal found 5/6$396
Sat 5/116:10 pmEYW - MDW
1 stop4h 51mDelta
Tue 5/1412:42 pmMDW - EYW
1 stop5h 58mDelta
Deal found 5/5$428
Sat 5/116:10 pmEYW - MDW
1 stop4h 51mDelta
Tue 5/148:45 amMDW - EYW
1 stop7h 27mDelta
Deal found 5/6$438

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 2,749,864 searches. Data last updated May 8, 2024.
Thu 5/166:10 pmEYW - MDW
1 stop4h 51mDelta
Thu 5/2312:42 pmMDW - EYW
1 stop5h 58mDelta
Deal found 5/6$428
Thu 5/166:10 pmEYW - MDW
1 stop4h 51mDelta
Thu 5/239:32 amMDW - EYW
2 stops9h 08mDelta
Deal found 5/6$880
Thu 5/167:05 amEYW - MDW
2 stops12h 02mDelta
Thu 5/239:32 amMDW - EYW
2 stops9h 08mDelta
Deal found 5/6$2,973

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 2,749,864 searches. Data last updated May 8, 2024.
Mon 7/296:00 pmEYW - MDW
1 stop4h 41mDelta
Deal found 5/5$254
Sun 7/282:44 pmEYW - MDW
1 stop7h 57mDelta
Deal found 5/5$279
Sat 7/272:44 pmEYW - MDW
1 stop7h 57mDelta
Deal found 5/5$359
Sat 7/277:25 amEYW - MDW
2 stops10h 40mDelta
Deal found 5/5$699
Mon 7/297:25 amEYW - MDW
2 stops10h 40mDelta
Deal found 5/5$769
Sun 7/287:25 amEYW - MDW
2 stops10h 40mDelta
Deal found 5/5$847

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 2,749,864 searches. Data last updated May 8, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$216 - $815

Route

Depart

Return

Price

Key WestChicago Midway

EYW - MDW

EYWMDW

Key West

Tue 9/10

1 stop4h 39m

Chicago Midway

Wed 9/18

1 stop5h 28m

$216

Key WestChicago Midway

EYW - MDW

EYWMDW

Key West

Tue 9/10

1 stop4h 39m

Chicago Midway

Mon 9/16

1 stop5h 28m

$297

Key WestChicago Midway

EYW - MDW

EYWMDW

Key West

Mon 6/3

1 stop4h 51m

Chicago Midway

Mon 6/10

1 stop5h 24m

$313

Key WestChicago Midway

EYW - MDW

EYWMDW

Key West

Fri 9/13

1 stop4h 39m

Chicago Midway

Wed 9/18

1 stop5h 28m

$317

Key WestChicago Midway

EYW - MDW

EYWMDW

Key West

Thu 9/12

1 stop4h 39m

Chicago Midway

Sun 9/15

1 stop4h 48m

$378

Key WestChicago Midway

EYW - MDW

EYWMDW

Key West

Fri 6/7

1 stop4h 46m

Chicago Midway

Mon 6/10

1 stop6h 20m

$388

Key WestChicago Midway

EYW - MDW

EYWMDW

Key West

Tue 9/10

1 stop4h 39m

Chicago Midway

Thu 9/19

1 stop8h 22m

$396

Key WestChicago Midway

EYW - MDW

EYWMDW

Key West

Mon 8/26

1 stop4h 42m

Chicago Midway

Sat 8/31

1 stop5h 58m

$518

Key WestChicago Midway

EYW - MDW

EYWMDW

Key West

Mon 8/26

1 stop4h 42m

Chicago Midway

Sat 8/31

2 stops9h 01m

$815

Flights are sorted by cheapest first

Deals found on 5/6

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

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 May 8, 2024.
Delta
8.1
Very good
10,810 reviews
Check prices

Boarding

8.2

Overall

8.1

Entertainment

8.0

Food

7.4

Comfort

7.9

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
8.1
Very good
10,810 reviews
Delta
8.1
Very good
10,810 reviews
Check prices

Boarding

8.2

Overall

8.1

Entertainment

8.0

Food

7.4

Comfort

7.9

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 $300 on Cheapflights?

    Yes, there are multiple flights from Key West to Chicago Midway Airport for under $300. The cheapest flight booked recently is on Delta for just $216, but on average you can expect to pay $613.

  • Are there last-minute flights available from Key West to Chicago Midway Airport for under $500?

    There are currently 3+ open flights from Key West to Chicago Midway Airport within the next 7 days for less than $500.

  • 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 5/7.

See more FAQs

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Search flights from Key West to Midway by cabin class

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

Cheapflights makes it easy to find Key West to Midway flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

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

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Midway from Key West.

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

Yes! Cheapflights helps users easily find flights from Key West to Midway with no change fees.

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

Yes! Start tracking prices for Key West to Midway flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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