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$33+ Cheap flights from Midway (MDW) to Florida Keys

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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
Oct 7 — Oct 141
From?
To?
Mon 10/7
Mon 10/14
1 adult, Economy
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Cheap Midway to Florida Keys flights in October & November 2024

Find cheap flight options from Midway to Florida Keys 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.
These are some of the most attractive deals on flights from Chicago to Florida Keys in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/48:03 pmMDW - MIA
Nonstop2h 58mFrontier
Fri 11/81:06 pmMIA - MDW
Nonstop3h 15mFrontier
Deal found 10/1$98
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.
Mon 10/281:30 pmMDW - MIA
Nonstop2h 55mSouthwest
Thu 10/312:50 pmMIA - MDW
Nonstop3h 05mSouthwest
Deal found 10/1$201
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 11/206:49 pmMDW - MIA
1 stop5h 04mDelta
Thu 11/2810:14 amMIA - MDW
1 stop5h 20mDelta
Deal found 10/1$216
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.
Sat 11/162:38 pmMDW - EYW
1 stop4h 52mDelta
Sat 11/237:25 amEYW - MDW
1 stop7h 28mDelta
Deal found 10/1$327

Midway to Florida Keys 2024 flight deals

Discover exclusive flight deals for travel between Midway and Florida Keys 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.
These are some of the most attractive deals on flights from Chicago to Florida Keys in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/292:31 pmMDW - MIA
1 stop5h 06mFrontier
Mon 11/44:58 pmMIA - MDW
Nonstop3h 10mFrontier
Deal found 10/1$112
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.
Mon 10/281:30 pmMDW - MIA
Nonstop2h 55mSouthwest
Thu 10/312:50 pmMIA - MDW
Nonstop3h 05mSouthwest
Deal found 10/1$201
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 11/206:49 pmMDW - MIA
1 stop5h 04mDelta
Thu 11/2810:14 amMIA - MDW
1 stop5h 20mDelta
Deal found 10/1$216
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.
Sat 11/162:38 pmMDW - EYW
1 stop4h 52mDelta
Sat 11/237:25 amEYW - MDW
1 stop7h 28mDelta
Deal found 10/1$327

Midway to Florida Keys flights leaving soon

Find last-minute flight options from Midway to Florida Keys 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.
Consider one of these great deals we found on last-minute flights from Chicago to Florida Keys. To prevent any unwanted surprises, users should verify their flight info before booking.
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/148:03 pmMDW - MIA
Nonstop2h 58mFrontier
Thu 10/176:00 amMIA - MDW
1 stop5h 54mFrontier
Deal found 9/30$135
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.
Tue 10/89:24 amMDW - MIA
1 stop6h 26mDelta
Fri 1/318:05 amMIA - MDW
1 stop5h 28mDelta
Deal found 10/1$262
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 10/81:00 pmMDW - MIA
1 stop6h 55mSouthwest
Fri 1/317:05 amMIA - MDW
2 stops10h 15mSouthwest
Deal found 10/1$316
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.
Wed 10/912:49 pmMDW - EYW
1 stop6h 29mDelta
Sun 10/132:11 pmEYW - MDW
1 stop4h 51mDelta
Deal found 10/2$548

One-way flights to Florida Keys from Midway

Search for one-way flight options from Midway to Florida Keys. 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.
Users in need of a one-way flight from Chicago to Florida Keys can choose from these deals. Users in need of a round-trip flight from Chicago to Florida Keys instead should update the search form at the top of page.
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.
Mon 10/288:03 pmMDW - MIA
Nonstop2h 58mFrontier
Deal found 10/2$33
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.
Tue 10/223:00 pmMDW - MIA
2 stops29h 05mMultiple Airlines
Deal found 9/30$89
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.
Wed 11/2012:43 pmMDW - EYW
1 stop6h 47mDelta
Deal found 10/2$108
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.
Mon 11/256:57 pmMDW - MIA
1 stop4h 56mDelta
Deal found 10/1$108
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.
Wed 11/209:40 amMDW - MIA
Nonstop3h 05mSouthwest
Deal found 10/2$109
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.
Thu 10/173:18 pmMDW - EYW
2 stops18h 17mAllegiant Air
Deal found 10/1$389

Find flights from Midway to Florida Keys within your budget

Customize your flight search to find flights from Midway to Florida Keys 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

$113 - $327

Route

Depart

Return

Price

Chicago MidwayMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 11/20

1 stop13h 31m

Miami

Tue 11/26

Nonstop3h 16m

$113

Chicago MidwayMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 10/28

Nonstop2h 55m

Miami

Thu 10/31

Nonstop3h 05m

$201

Chicago MidwayMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 1/11

1 stop4h 42m

Miami

Fri 1/17

1 stop5h 28m

$216

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Sat 11/16

1 stop4h 52m

Key West

Sat 11/23

1 stop7h 28m

$327

Flights are sorted by cheapest first

Deals found on 10/2

Best time to book a flight from Midway to Florida Keys

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

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

What are the most popular airlines that fly from Chicago Midway Airport to Florida Keys?

Our users search for these airlines the most when looking for flights from Midway to Florida Keys. Data last updated on October 2, 2024.

Before booking your flight from Chicago Midway Airport to Florida Keys check out the most popular airlines for this route: Frontier, Delta or Southwest.

Frontier

Frontier

From $52

Delta

Delta

From $246

Southwest

Southwest

From $214

Spirit Airlines

Spirit Airlines

From $69

Rainfall in Florida Keys by month

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

In terms of precipitation, rainfall in Florida Keys ranges from 1.6 - 9.9 inches per month. September is typically the wettest month, when rainfall can reach 9.9 in. January is typically the driest time to visit Florida Keys when rainfall is around 1.6 in.

Temperature in Florida Keys by month

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

If weather is an important factor for your trip to Florida Keys, 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 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 68.0 F).

Reviews of airlines servicing Florida Keys

Get insights into the airlines that provide service to Florida Keys. 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 Florida Keys. Reviews last updated October 2, 2024.
See what other customers who have flown with Frontier, Southwest and Delta from Chicago to Florida Keys have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very good
5,246 reviews

Crew

8.7

Food

7.2

Boarding

8.3

Entertainment

7.7

Overall

8.2

Comfort

8.1

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

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

Crew

8.7

Food

7.2

Boarding

8.3

Entertainment

7.7

Overall

8.2

Comfort

8.1

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

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

Crew

8.7

Food

7.2

Boarding

8.3

Entertainment

7.7

Overall

8.2

Comfort

8.1

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

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

Crew

8.7

Food

7.2

Boarding

8.3

Entertainment

7.7

Overall

8.2

Comfort

8.1

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

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

Crew

8.7

Food

7.2

Boarding

8.3

Entertainment

7.7

Overall

8.2

Comfort

8.1

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from Midway to Florida Keys. 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 Chicago Midway Airport to Florida Keys for under $200 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to Florida Keys for under $200. The cheapest flight booked recently is on Frontier for just $113, but on average you can expect to pay $214.

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

    Cheapflights has at least 2 direct flights from Chicago Midway Airport to Florida Keys under $100. A good price for a nonstop flight from Chicago Midway Airport to Florida Keys is less than $117.

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

    There are currently 4+ open flights from Chicago Midway Airport to Florida Keys within the next 7 days for less than $200.

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

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $33. Users have also found prices from $108 and $109 on Delta and Southwest, respectively.

  • What does MDW to EYW mean?

    Great question - MDW to EYW just means Chicago Midway Airport to Key West Airport. Now you’ll know what these unique codes when you look for flights! Marathon Airport (MTH), Key West Nas Airport (NQX), Key Largo Ocean Reef Airport (OCA), Port Largo Airport (KYL) are some additional IATA codes for airports related to your trip.

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

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

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

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

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

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

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

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

    Many airlines flying from Midway to Florida Keys 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 Florida Keys?

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

    The Chicago Midway Airport to Florida Keys flight deals you see on this page were last updated on 10/1.

See more FAQs

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Top airline flying from Midway to Florida Keys

Discover the top airline that operate flights from Midway to Florida Keys. 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 2,666,977 searches. Data last updated October 2, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$247Average$547FlexibilityNo cancel feeOn-timeN/A
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