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$89+ 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 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$177
(Southwest)

One-way from

$89
(Southwest)

Popular in

December

Cheapest in

July

Average price

$269
Provider with most accurate pricing for Chicago (CHI)-Miami flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Miami flights.
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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. 14% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 17, 2025.

This Southwest deal was found by Cheapflights users on 4/17. 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 5/177:25 amMDW - MIA
Nonstop3h 00mSouthwest
Tue 5/207:00 amMIA - MDW
Nonstop3h 10mSouthwest
Deal found 4/17$177
This Lucky2Go deal was found by Cheapflights users on 4/17. 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 Lucky2Go is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/256:10 amMDW - MIA
1 stop24h 48mFrontier
Wed 5/289:30 amMIA - MDW
1 stop14h 06mFrontier
Deal found 4/17$204
This Delta deal was found by Cheapflights users on 4/17. 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 5/174:15 pmMDW - MIA
1 stop7h 22mDelta
Tue 5/205:35 amMIA - MDW
1 stop7h 18mDelta
Deal found 4/17$217
This Delta deal was found by Cheapflights users on 4/17. 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 7/810:35 amMDW - EYW
1 stop5h 40mDelta
Wed 7/96:00 pmEYW - MDW
1 stop4h 47mDelta
Deal found 4/17$323

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 April 17, 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

Sat 5/17

7:25 am-11:25 am

Nonstop3h 00m

Miami

Tue 5/20

7:00 am-9:10 am

Nonstop3h 10m

$177

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 5/25

6:10 am-7:58 am

1 stop24h 48m

Miami

Wed 5/28

9:30 am-10:36 pm

1 stop14h 06m

$204

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 5/17

4:15 pm-12:37 am

1 stop7h 22m

Miami

Tue 5/20

5:35 am-11:53 am

1 stop7h 18m

$217

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 7/8

10:35 am-5:15 pm

1 stop5h 40m

Key West

Wed 7/9

6:00 pm-9:47 pm

1 stop4h 47m

$323

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 5/17

6:45 pm-10:40 pm

Nonstop2h 55m

$89

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 5/17

4:15 pm-12:37 am

1 stop7h 22m

$109

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 5/8

6:30 pm-7:58 am

1 stop12h 28m

$111

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 6/16

8:36 pm-8:00 pm

2 stops22h 24m

$144

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 5/7

10:25 am-5:30 pm

1 stop6h 05m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

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 April 17, 2025.
See what other customers who have flown with Southwest, Delta and Frontier 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

Comfort

8.0

Overall

8.0

Food

7.1

Crew

8.6

Boarding

8.2

Entertainment

7.6

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

Comfort

8.0

Overall

8.0

Food

7.1

Crew

8.6

Boarding

8.2

Entertainment

7.6

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
7,917 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Overall

8.0

Food

7.1

Crew

8.6

Boarding

8.2

Entertainment

7.6

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
6.0
Okay
3,281 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Overall

8.0

Food

7.1

Crew

8.6

Boarding

8.2

Entertainment

7.6

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 $89. Users have also found prices from $109 and $111 on Delta and Frontier, 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.

See more FAQs

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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 2 airlines flying from Midway to Florida Keys

Discover the top 2 airlines 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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$247Average$478FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$324Average$464FlexibilityNo cancel feeOn-time69%

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