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$54+ 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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
Jan 27 — Feb 31
Mon 1/27
Mon 2/3
1 adult, Economy
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Cheap flight deals from Midway to Florida Keys

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Florida Keys (zzEOA). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 22, 2025.

Round-trip from

$104
(CheapOair)

One-way from

$54
(Trip.com)
From Chicago Midway to Florida Keys
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One-way flight from Chicago Midway to Florida Keys
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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 January 22, 2025.

This Trip.com deal was found by Cheapflights users on 1/21. 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.
Tue 2/187:25 amMDW - MIA
Nonstop3h 12mFrontier
Tue 2/259:42 pmMIA - MDW
1 stop10h 25mFrontier
Deal found 1/21$105
This Delta deal was found by Cheapflights users on 1/21. 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 2/182:08 pmMDW - MIA
1 stop6h 34mDelta
Fri 2/286:00 amMIA - MDW
1 stop5h 12mDelta
Deal found 1/21$217
This Southwest deal was found by Cheapflights users on 1/21. 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 3/245:35 pmMDW - MIA
Nonstop3h 00mSouthwest
Thu 3/277:40 amMIA - MDW
Nonstop3h 15mSouthwest
Deal found 1/21$237
This Delta deal was found by Cheapflights users on 1/22. 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 4/1112:48 pmMDW - EYW
1 stop6h 38mDelta
Tue 4/156:00 pmEYW - MDW
1 stop5h 29mDelta
Deal found 1/22$289
This Trip.com deal was found by Cheapflights users on 1/22. 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.
Mon 2/107:15 amMDW - EYW
1 stop9h 00mMultiple Airlines
Sat 2/1510:00 amEYW - MDW
1 stop13h 51mMultiple Airlines
Deal found 1/22$300

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 2,558,603 searches. Data last updated January 22, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 2/12

7:25 am-11:37 am

Nonstop3h 12m

Miami

Tue 2/18

9:42 pm-7:07 am

1 stop10h 25m

$104

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 2/18

2:08 pm-9:42 pm

1 stop6h 34m

Miami

Thu 2/27

8:10 am-11:59 am

1 stop4h 49m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 3/24

5:35 pm-9:35 pm

Nonstop3h 00m

Miami

Thu 3/27

7:40 am-9:55 am

Nonstop3h 15m

$237

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Mon 2/24

6:59 pm-2:08 pm

2 stops18h 09m

Key West

Wed 3/5

6:14 pm-10:20 pm

1 stop5h 06m

$288

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Mon 2/10

7:15 am-5:15 pm

1 stop9h 00m

Key West

Sat 2/15

10:00 am-10:51 pm

1 stop13h 51m

$300

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 2/12

6:00 am-3:35 pm

1 stop8h 35m

$54

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 2/11

12:44 pm-8:11 pm

1 stop6h 27m

$109

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 2/17

2:08 pm-9:42 pm

1 stop6h 34m

$109

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 3/24

5:35 pm-9:35 pm

Nonstop3h 00m

$119

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sat 2/15

12:43 pm-10:10 am

1 stop20h 27m

$180

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/22

Showing 1-10 of 12 results
1
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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.

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.

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 January 22, 2025.
See what other customers who have flown with Frontier, Delta and Southwest 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
8.1
Very good
4,654 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Overall

8.1

Food

7.2

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
8.1
Very good
4,654 reviews
Southwest
8.1
Very good
4,654 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Overall

8.1

Food

7.2

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
8,512 reviews
Southwest
8.1
Very good
4,654 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Overall

8.1

Food

7.2

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
801 reviews
Southwest
8.1
Very good
4,654 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Overall

8.1

Food

7.2

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
3,441 reviews
Southwest
8.1
Very good
4,654 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Overall

8.1

Food

7.2

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.

  • 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 $54. Users have also found prices from $109 and $119 on Delta and Southwest, 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 $531). 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 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 January 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$525FlexibilityNo cancel feeOn-timeN/A
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