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Florida Keys

$67+ 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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
Aug 10 — Aug 171
Sun 8/10
Sun 8/17
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 August 5, 2025.

Round-trip from

$132
(Southwest)

One-way from

$67
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$206
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. 11% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 5, 2025.

This Southwest deal was found by Cheapflights users on 8/5. 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 9/82:10 pmMDW - MIA
Nonstop3h 00mSouthwest
Sat 9/134:05 pmMIA - MDW
Nonstop3h 10mSouthwest
Deal found 8/5$132
This Southwest deal was found by Cheapflights users on 8/4. 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 8/4$137
This Southwest deal was found by Cheapflights users on 8/5. 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 9/26:25 amMDW - MIA
1 stop6h 40mSouthwest
Thu 9/412:35 pmMIA - MDW
Nonstop3h 10mSouthwest
Deal found 8/5$143
This Southwest deal was found by Cheapflights users on 8/3. 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 9/38:35 amMDW - MIA
1 stop7h 05mSouthwest
Sat 9/66:05 amMIA - MDW
1 stop6h 05mSouthwest
Deal found 8/3$146
This Southwest deal was found by Cheapflights users on 8/4. 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 9/63:55 pmMDW - MIA
1 stop4h 45mSouthwest
Mon 9/812:35 pmMIA - MDW
Nonstop3h 10mSouthwest
Deal found 8/4$147
This Southwest deal was found by Cheapflights users on 8/4. 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 9/38:35 amMDW - MIA
1 stop7h 05mSouthwest
Wed 9/1011:40 amMIA - MDW
2 stops8h 30mSouthwest
Deal found 8/4$151
This Southwest deal was found by Cheapflights users on 8/4. 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 8/279:00 amMDW - MIA
1 stop6h 20mSouthwest
Wed 9/39:00 amMIA - MDW
1 stop9h 10mSouthwest
Deal found 8/4$153
This Frontier deal was found by Cheapflights users on 8/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2310:03 pmMDW - MIA
Nonstop3h 00mFrontier
Mon 10/276:53 pmMIA - MDW
Nonstop3h 15mFrontier
Deal found 8/4$155
This Southwest deal was found by Cheapflights users on 8/5. 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 9/63:55 pmMDW - MIA
1 stop4h 45mSouthwest
Sat 9/136:05 amMIA - MDW
2 stops8h 25mSouthwest
Deal found 8/5$157
This Delta deal was found by Cheapflights users on 8/3. 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 8/256:00 amMDW - EYW
1 stop6h 05mDelta
Wed 9/37:00 amEYW - MDW
1 stop7h 36mDelta
Deal found 8/3$269
This Delta deal was found by Cheapflights users on 8/4. 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 8/2112:43 pmMDW - EYW
1 stop6h 29mDelta
Tue 8/266:00 pmEYW - MDW
1 stop4h 44mDelta
Deal found 8/4$289
This Delta deal was found by Cheapflights users on 8/3. 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 9/136:00 amMDW - EYW
1 stop6h 02mDelta
Tue 9/167:00 amEYW - MDW
1 stop5h 48mDelta
Deal found 8/3$320

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 August 5, 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

Mon 9/8

2:10 pm-6:10 pm

Nonstop3h 00m

Miami

Sat 9/13

4:05 pm-6:15 pm

Nonstop3h 10m

$132

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

Tue 9/2

6:25 am-2:05 pm

1 stop6h 40m

Miami

Thu 9/4

12:35 pm-2:45 pm

Nonstop3h 10m

$143

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 9/3

8:35 am-4:40 pm

1 stop7h 05m

Miami

Sat 9/6

6:05 am-11:10 am

1 stop6h 05m

$146

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 9/6

3:55 pm-9:40 pm

1 stop4h 45m

Miami

Mon 9/8

12:35 pm-2:45 pm

Nonstop3h 10m

$147

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 9/3

8:35 am-4:40 pm

1 stop7h 05m

Miami

Wed 9/10

11:40 am-7:10 pm

2 stops8h 30m

$151

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 8/27

9:00 am-4:20 pm

1 stop6h 20m

Miami

Wed 9/3

9:00 am-5:10 pm

1 stop9h 10m

$153

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 10/23

10:03 pm-2:03 am

Nonstop3h 00m

Miami

Mon 10/27

6:53 pm-9:08 pm

Nonstop3h 15m

$155

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 9/6

3:55 pm-9:40 pm

1 stop4h 45m

Miami

Sat 9/13

6:05 am-1:30 pm

2 stops8h 25m

$157

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Mon 8/25

6:00 am-1:05 pm

1 stop6h 05m

Key West

Wed 9/3

7:00 am-1:36 pm

1 stop7h 36m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/5

Showing 1-10 of 35 results
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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 $492). 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.

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 August 5, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Frontier from Chicago Midway Airport to Florida Keys. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

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
7,985 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

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
3,232 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

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.

  • 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 $492). 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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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 August 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$225Average$526FlexibilityNo cancel feeOn-timeN/A

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