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$69+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
1 adult, Economy
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Cheap flight deals from Midway to Florida Keys

Keep the following information in mind while searching for Midway to Florida Keys flight deals. Data was last updated June 18, 2025.

Round-trip from

$137
(Southwest)

One-way from

$69
(Southwest)

Popular in

March

Cheapest in

September

Average price

$276
From Chicago Midway to Florida Keys
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One-way flight from Chicago Midway to Florida Keys
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Highest demand for flights based on searches. 12% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Find flight deals from Midway to Florida Keys

Cheapest flights from Midway to Florida Keys
Explore the most affordable flight options available from Midway to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 18, 2025.

This Southwest deal was found by Cheapflights users on 6/16. 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.
Thu 9/42:10 pmMDW - MIA
Nonstop3h 00mSouthwest
Sun 9/77:30 amMIA - MDW
Nonstop3h 05mSouthwest
Deal found 6/16$137
This KAYAK deal was found by Cheapflights users on 6/15. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1910:03 pmMDW - MIA
Nonstop3h 00mFrontier
Sun 10/266:53 pmMIA - MDW
Nonstop3h 15mFrontier
Deal found 6/15$193
This Delta deal was found by Cheapflights users on 6/16. 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 8/301:08 pmMDW - MIA
1 stop7h 22mDelta
Thu 9/48:10 amMIA - MDW
1 stop5h 18mDelta
Deal found 6/16$222
This Delta deal was found by Cheapflights users on 6/16. 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 8/2210:11 amMDW - EYW
1 stop6h 16mDelta
Sat 8/2311:52 amEYW - MDW
1 stop4h 36mDelta
Deal found 6/16$330
This Mytrip deal was found by Cheapflights users on 6/16. 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 7/3111:37 amMDW - EYW
2 stops27h 59mAllegiant Air
Thu 8/78:54 amEYW - MDW
2 stops28h 27mAllegiant Air
Deal found 6/16$353

Cheapflights Fare Finder

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 2,558,603 searches. Data last updated June 18, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Florida Keys that are best for you.

Fly from

Midway

Fly to

Florida Keys

Route

Depart

Return

Price

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 9/4

2:10 pm-6:10 pm

Nonstop3h 00m

Miami

Sun 9/7

7:30 am-9:35 am

Nonstop3h 05m

$137

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 8/30

1:08 pm-9:30 pm

1 stop7h 22m

Miami

Thu 9/4

8:10 am-12:28 pm

1 stop5h 18m

$222

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 8/22

10:11 am-5:27 pm

1 stop6h 16m

Key West

Sat 8/23

11:52 am-3:28 pm

1 stop4h 36m

$330

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 8/21

2:05 pm-9:35 pm

1 stop6h 30m

Miami

Sun 8/24

9:08 am-2:41 pm

1 stop6h 33m

$345

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Thu 7/31

11:37 am-4:36 pm

2 stops27h 59m

Key West

Thu 8/7

8:54 am-12:21 pm

2 stops28h 27m

$353

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 9/1

2:10 pm-6:10 pm

Nonstop3h 00m

$69

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 8/12

12:43 pm-9:28 pm

1 stop7h 45m

$109

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Fri 7/18

12:50 pm-10:29 pm

1 stop8h 39m

$171

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Fri 6/27

10:34 am-8:00 pm

2 stops32h 26m

$196

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 7/15

12:43 pm-7:49 pm

1 stop6h 06m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/17

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Florida Keys

What is the cheapest month to book a flight from Chicago Midway Airport to Florida Keys?

Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Florida Keys (average of $328). Flying from Chicago Midway Airport to Florida Keys in March is currently the most expensive (average of $493). 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.

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 June 18, 2025.
See what other customers who have flown with Southwest, Delta and Allegiant Air 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
8.0
Very good
4,280 reviews

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

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
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

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
7,965 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

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
7.3
Good
722 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

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
5.9
Fair
3,301 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

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.

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

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $69. Users have also found prices from $96 and $109 on Frontier and Delta, respectively.

  • 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Florida Keys?

    Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Florida Keys (average of $328). Flying from Chicago Midway Airport to Florida Keys in March is currently the most expensive (average of $493). 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.

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Alternative routes for Midway to Florida Keys

See prices for flight routes from nearby airports that may be better suited for you.
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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 2,558,603 searches. Data last updated June 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$438FlexibilityNo cancel feeOn-timeN/A

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