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$59+ Cheap flights from Florida Keys to Midway (MDW)

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 2/20. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MDW
Dec 28 — Jan 41
Sat 12/28
Sat 1/4
1 adult, Economy
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Cheap flight deals from Florida Keys to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Florida Keys (zzEOA) to Midway (MDW). 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 December 23, 2024.

Round-trip from

$116
(Cheapflightsfares)

One-way from

$59
(Cheapflightsfares)
From Florida Keys to Chicago Midway
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One-way flight from Florida Keys to Chicago Midway
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Find flight deals from Florida Keys to Midway

Cheapest flights from Florida Keys to Midway
Explore the most affordable flight options available from Florida Keys to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 23, 2024.

This Frontier deal was found by Cheapflights users on 12/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3112:43 pmMIA - MDW
Nonstop3h 30mFrontier
Thu 1/97:30 amMDW - MIA
Nonstop3h 13mFrontier
Deal found 12/22$159
This Southwest deal was found by Cheapflights users on 12/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/306:30 amMIA - MDW
1 stop9h 20mSouthwest
Tue 12/311:30 pmMDW - MIA
2 stops7h 30mSouthwest
Deal found 12/22$639
This Delta deal was found by Cheapflights users on 12/22. 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.
Tue 12/315:45 pmMIA - MDW
1 stop5h 21mDelta
Thu 1/29:30 amMDW - MIA
2 stops8h 10mDelta
Deal found 12/22$783
This Delta deal was found by Cheapflights users on 12/22. 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.
Wed 12/253:50 pmEYW - MDW
1 stop7h 16mDelta
Sun 12/2912:10 pmMDW - EYW
1 stop7h 42mDelta
Deal found 12/22$1,088

Find flights from Florida Keys to Midway within your budget

Customize your flight search to find flights from Florida Keys to Midway 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 December 23, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 2/20

12:42 pm-3:13 pm

Nonstop3h 31m

Chicago Midway

Thu 2/27

7:25 am-11:37 am

Nonstop3h 12m

$116

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 1/23

5:45 am-6:26 pm

2 stops13h 41m

Chicago Midway

Mon 1/27

6:15 am-12:49 pm

1 stop5h 34m

$149

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 1/17

5:55 pm-8:15 pm

Nonstop3h 20m

Chicago Midway

Wed 1/22

6:10 pm-10:10 pm

Nonstop3h 00m

$178

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 2/14

8:00 am-1:05 pm

1 stop6h 05m

Chicago Midway

Mon 2/17

2:08 pm-9:42 pm

1 stop6h 34m

$216

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 1/8

6:16 pm-10:20 pm

1 stop5h 04m

Chicago Midway

Sat 1/11

6:00 am-11:38 am

1 stop4h 38m

$378

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 2/20

3:52 pm-6:20 pm

Nonstop3h 28m

$59

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 1/22

4:40 pm-6:55 pm

Nonstop3h 15m

$79

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 1/25

6:00 am-10:12 am

1 stop5h 12m

$108

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 3/5

1:02 pm-5:36 pm

3 stops29h 34m

$233

Key WestChicago

EYW - MDW

EYWMDW

Key West

Sat 12/28

6:13 pm-10:06 pm

1 stop4h 53m

$369

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Best time to book a flight from Florida Keys to Midway

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

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

Rainfall in Midway by month

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

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

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

If weather is an important factor for your trip to Chicago Midway Airport, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated December 23, 2024.
Read through reviews of airlines operating flights from Florida Keys to Chicago, such as Delta, Frontier and Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,780 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

Crew

8.7

Boarding

8.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.1
Very good
4,780 reviews
Southwest
8.1
Very good
4,780 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

Crew

8.7

Boarding

8.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Delta
8.0
Very good
8,594 reviews
Southwest
8.1
Very good
4,780 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

Crew

8.7

Boarding

8.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Frontier
6.1
Okay
3,469 reviews
Southwest
8.1
Very good
4,780 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

Crew

8.7

Boarding

8.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Related info for your journey

Find useful and relevant information for your journey from Florida Keys to Midway. 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 Florida Keys to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $59 on Frontier. Other airlines that offer cheap prices include Southwest from $79 and Delta from $108 one-way.

  • Can I find deals for flights from Florida Keys to Midway that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Florida Keys to Midway 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 Florida Keys to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Florida Keys to Chicago Midway Airport (average of $160). Flying from Florida Keys to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 Florida Keys to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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