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$49+ Cheap flights from Florida Keys 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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MDW
Oct 7 — Oct 141
From?
To?
Mon 10/7
Mon 10/14
1 adult, Economy
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Cheap Florida Keys to Midway flights in October & November 2024

Find cheap flight options from Florida Keys to Midway specifically for the months of October and November 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,666,977 searches. Prices were last updated on October 2, 2024.
Scroll through some of the best deals on flights from Florida Keys to Chicago in 2024. Check back in a little while for more flight options.
This Cheapflightsfares deal was found by Cheapflights users on 10/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/246:00 amMIA - MDW
1 stop5h 54mFrontier
Mon 10/288:03 pmMDW - MIA
Nonstop2h 58mFrontier
Deal found 10/2$86
This eDestinos deal was found by Cheapflights users on 10/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/309:00 amMIA - MDW
1 stop7h 50mMultiple Airlines
Sun 11/35:00 amMDW - MIA
2 stops29h 09mMultiple Airlines
Deal found 10/1$154
This Southwest deal was found by Cheapflights users on 10/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/53:40 pmMIA - MDW
Nonstop3h 10mSouthwest
Sat 11/912:00 pmMDW - MIA
Nonstop3h 05mSouthwest
Deal found 10/2$169
This Delta deal was found by Cheapflights users on 9/30. 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 11/68:25 amMIA - MDW
1 stop5h 49mDelta
Sat 11/162:38 pmMDW - MIA
1 stop5h 41mDelta
Deal found 9/30$216
This Delta deal was found by Cheapflights users on 10/2. 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 10/267:25 amEYW - MDW
1 stop6h 49mDelta
Sun 11/35:00 amMDW - EYW
1 stop4h 40mDelta
Deal found 10/2$262

Florida Keys to Midway 2024 flight deals

Discover exclusive flight deals for travel between Florida Keys and Midway in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,666,977 searches. Data last updated October 2, 2024.
Scroll through some of the best deals on flights from Florida Keys to Chicago in 2024. Check back in a little while for more flight options.
This Cheapflightsfares deal was found by Cheapflights users on 10/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/246:00 amMIA - MDW
1 stop5h 54mFrontier
Mon 10/288:03 pmMDW - MIA
Nonstop2h 58mFrontier
Deal found 10/2$86
This eDestinos deal was found by Cheapflights users on 10/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/309:00 amMIA - MDW
1 stop7h 50mMultiple Airlines
Sun 11/35:00 amMDW - MIA
2 stops29h 09mMultiple Airlines
Deal found 10/1$154
This Southwest deal was found by Cheapflights users on 10/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/53:40 pmMIA - MDW
Nonstop3h 10mSouthwest
Sat 11/912:00 pmMDW - MIA
Nonstop3h 05mSouthwest
Deal found 10/2$169
This Delta deal was found by Cheapflights users on 9/30. 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 11/68:25 amMIA - MDW
1 stop5h 49mDelta
Sat 11/162:38 pmMDW - MIA
1 stop5h 41mDelta
Deal found 9/30$216
This Delta deal was found by Cheapflights users on 10/2. 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 10/267:25 amEYW - MDW
1 stop6h 49mDelta
Sun 11/35:00 amMDW - EYW
1 stop4h 40mDelta
Deal found 10/2$262

Florida Keys to Midway flights leaving soon

Find last-minute flight options from Florida Keys 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 2,666,977 searches. Data last updated October 2, 2024.
Book one of these great deals on flights from Florida Keys to Chicago. Tip: verify your flight details before completing your reservation.
This eDestinos deal was found by Cheapflights users on 9/30. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/119:10 pmMIA - MDW
1 stop17h 49mFrontier
Mon 10/148:03 pmMDW - MIA
Nonstop2h 58mFrontier
Deal found 9/30$178
This eDestinos deal was found by Cheapflights users on 10/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/99:38 amMIA - MDW
2 stops26h 16mMultiple Airlines
Wed 10/1611:54 amMDW - MIA
1 stop7h 43mMultiple Airlines
Deal found 10/1$224
This Delta deal was found by Cheapflights users on 10/1. 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 10/98:25 amMIA - MDW
1 stop7h 29mDelta
Tue 10/159:24 amMDW - MIA
1 stop6h 26mDelta
Deal found 10/1$298
This Southwest deal was found by Cheapflights users on 9/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/123:25 pmMIA - MDW
Nonstop3h 05mSouthwest
Mon 10/141:30 pmMDW - MIA
Nonstop2h 55mSouthwest
Deal found 9/30$400
This Mytrip deal was found by Cheapflights users on 9/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/115:06 pmMIA - MDW
2 stops17h 41mVolaris
Mon 10/148:45 pmMDW - MIA
1 stop16h 10mVolaris
Deal found 9/30$1,006

One-way flights to Midway from Florida Keys

Search for one-way flight options from Florida Keys 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 2,666,977 searches. Data last updated October 2, 2024.
Take a look at some of the one-way flights we've detected from Florida Keys to Chicago. Users can also find round-trip Florida Keys to Chicago flights by using the search form above.
This Cheapflightsfares deal was found by Cheapflights users on 10/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/14:58 pmMIA - MDW
Nonstop3h 10mFrontier
Deal found 10/2$49
This Trip.com deal was found by Cheapflights users on 10/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/69:38 amMIA - MDW
1 stop14h 14mMultiple Airlines
Deal found 10/1$76
This Southwest deal was found by Cheapflights users on 10/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/53:40 pmMIA - MDW
Nonstop3h 10mSouthwest
Deal found 10/1$79
This Delta deal was found by Cheapflights users on 10/2. 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 10/318:05 amMIA - MDW
1 stop5h 27mDelta
Deal found 10/2$108
This Delta deal was found by Cheapflights users on 9/30. 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.
Tue 12/176:25 pmEYW - MDW
1 stop4h 42mDelta
Deal found 9/30$219
This Mytrip deal was found by Cheapflights users on 10/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/104:08 pmMIA - MDW
2 stops17h 02mVolaris
Deal found 10/1$374
This Mytrip deal was found by Cheapflights users on 10/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/305:45 pmEYW - MDW
2 stops19h 01mAllegiant Air
Deal found 10/1$387

Find flights from Florida Keys to Midway within your budget

Customize your flight search to find flights from Florida Keys 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 2,666,977 searches. Data last updated October 2, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$91 - $262

Route

Depart

Return

Price

MiamiChicago Midway

MIA - MDW

MIAMDW

Miami

Thu 10/24

1 stop5h 54m

Chicago Midway

Mon 10/28

Nonstop2h 58m

$91

MiamiChicago Midway

MIA - MDW

MIAMDW

Miami

Wed 11/6

1 stop17h 12m

Chicago Midway

Fri 11/8

Nonstop3h 24m

$147

MiamiChicago Midway

MIA - MDW

MIAMDW

Miami

Wed 11/6

Nonstop3h 10m

Chicago Midway

Sat 11/9

Nonstop3h 05m

$169

MiamiChicago Midway

MIA - MDW

MIAMDW

Miami

Wed 10/23

1 stop5h 27m

Chicago Midway

Mon 10/28

1 stop5h 45m

$227

Key WestChicago Midway

EYW - MDW

EYWMDW

Key West

Sat 10/26

1 stop6h 49m

Chicago Midway

Sun 11/3

1 stop4h 40m

$262

Flights are sorted by cheapest first

Deals found on 10/1

Best time to book a flight from Florida Keys to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Florida Keys 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.

Travel insights for flights from Florida Keys to Midway

Get recent, data-driven insights about flights from Florida Keys to Midway including ideal travel times, pricing trends, and more.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 October 2, 2024.
Read through reviews of airlines operating flights from Florida Keys to Chicago, such as Frontier, Southwest and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very good
5,246 reviews

Comfort

8.1

Boarding

8.3

Food

7.2

Overall

8.2

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.2
Very good
5,246 reviews
Southwest
8.2
Very good
5,246 reviews

Comfort

8.1

Boarding

8.3

Food

7.2

Overall

8.2

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Delta
8.0
Very good
9,007 reviews
Southwest
8.2
Very good
5,246 reviews

Comfort

8.1

Boarding

8.3

Food

7.2

Overall

8.2

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Allegiant Air
7.4
Good
879 reviews
Southwest
8.2
Very good
5,246 reviews

Comfort

8.1

Boarding

8.3

Food

7.2

Overall

8.2

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Volaris
6.7
Okay
1,335 reviews
Southwest
8.2
Very good
5,246 reviews

Comfort

8.1

Boarding

8.3

Food

7.2

Overall

8.2

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Frontier
6.1
Okay
3,659 reviews
Southwest
8.2
Very good
5,246 reviews

Comfort

8.1

Boarding

8.3

Food

7.2

Overall

8.2

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Related info for your journey

Find useful and relevant information for your journey from Florida Keys to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find flights from Florida Keys to Chicago Midway Airport for under $100 on Cheapflights?

    Yes, there are multiple flights from Florida Keys to Chicago Midway Airport for under $100. The cheapest flight booked recently is on Frontier for just $91, but on average you can expect to pay $179.

  • Are there nonstop flights from Florida Keys to Chicago Midway Airport for under $100 on Cheapflights?

    Cheapflights has at least 2 direct flights from Florida Keys to Chicago Midway Airport under $100. A good price for a nonstop flight from Florida Keys to Chicago Midway Airport is less than $133.

  • Are there last-minute flights available from Florida Keys to Chicago Midway Airport for under $200?

    There are currently 5+ open flights from Florida Keys to Chicago Midway Airport within the next 7 days for less than $200.

  • What are the cheapest airlines to fly from Florida Keys to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $49 on Frontier. Other airlines that offer cheap prices include Southwest from $79 and Delta from $108 one-way.

  • What does EYW to MDW mean?

    EYW stands for Key West Airport, while MDW stands for Chicago Midway 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. This flight route has multiple associated airports, so we think it might be helpful to learn the name and codes of them as well. They are Marathon Airport (MTH), Key West Nas Airport (NQX), Key Largo Ocean Reef Airport (OCA), Port Largo Airport (KYL).

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

    The amount of baggage you can bring on your Florida Keys 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 Florida Keys to Midway with specific airlines?

    Yes, Cheapflights allows you to browse and filter Florida Keys 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 Florida Keys to Midway that include hotel bookings?

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

  • How can I find direct flights from Florida Keys to Midway?

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

  • Can I find deals for business class flights from Florida Keys to Midway?

    Yes. Cheapflights offers flight deals from Florida Keys 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 Florida Keys to Midway that allow pets onboard?

    Many airlines flying from Florida Keys 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 Florida Keys to Midway?

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

    The Florida Keys to Chicago Midway Airport flight deals you see on this page were last updated on 10/2.

See more FAQs

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