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$60+ 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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MDW
Jan 27 — Feb 31
Mon 1/27
Mon 2/3
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 January 22, 2025.

Round-trip from

$97
(Cheapflightsfares)

One-way from

$60
(Flightnetwork)
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 January 22, 2025.

This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/61:36 pmMIA - MDW
1 stop5h 50mFrontier
Sun 2/97:25 amMDW - MIA
Nonstop3h 12mFrontier
Deal found 1/22$97
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 2/1411:33 amMIA - MDW
1 stop7h 38mDelta
Mon 2/172:08 pmMDW - MIA
1 stop6h 34mDelta
Deal found 1/22$217
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/258:20 amMIA - MDW
Nonstop3h 15mSouthwest
Tue 3/253:35 pmMDW - MIA
1 stop6h 15mSouthwest
Deal found 1/22$218
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.
Wed 3/56:14 pmEYW - MDW
1 stop5h 06mDelta
Mon 3/1012:51 pmMDW - EYW
1 stop6h 39mDelta
Deal found 1/21$243

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 January 22, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 2/6

12:42 pm-3:13 pm

Nonstop3h 31m

Chicago Midway

Mon 2/10

4:08 pm-12:12 am

1 stop7h 04m

$99

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 2/14

11:33 am-6:11 pm

1 stop7h 38m

Chicago Midway

Mon 2/17

2:08 pm-9:42 pm

1 stop6h 34m

$217

MiamiChicago

MIA - MDW

MIAMDW

Miami

Tue 3/25

8:20 am-10:35 am

Nonstop3h 15m

Chicago Midway

Tue 3/25

3:35 pm-10:50 pm

1 stop6h 15m

$218

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 3/5

6:14 pm-10:20 pm

1 stop5h 06m

Chicago Midway

Mon 3/10

12:51 pm-8:30 pm

1 stop6h 39m

$243

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 2/12

7:50 am-6:23 pm

1 stop11h 33m

$60

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 3/26

8:20 am-10:35 am

Nonstop3h 15m

$90

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 2/20

11:33 am-6:11 pm

1 stop7h 38m

$109

Key WestChicago

EYW - MDW

EYWMDW

Key West

Sat 3/1

10:00 am-10:51 pm

1 stop13h 51m

$153

Key WestChicago

EYW - MDW

EYWMDW

Key West

Sat 2/15

6:14 pm-10:20 pm

1 stop5h 06m

$260

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/22

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 January 22, 2025.
Read through reviews of airlines operating flights from Florida Keys to Chicago, such as Frontier, Delta and Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,654 reviews

Entertainment

7.7

Boarding

8.2

Food

7.2

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

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

Entertainment

7.7

Boarding

8.2

Food

7.2

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Delta
8.0
Very good
8,512 reviews
Southwest
8.1
Very good
4,654 reviews

Entertainment

7.7

Boarding

8.2

Food

7.2

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Frontier
6.1
Okay
3,441 reviews
Southwest
8.1
Very good
4,654 reviews

Entertainment

7.7

Boarding

8.2

Food

7.2

Comfort

8.1

Crew

8.7

Overall

8.1

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 $60 on Frontier. Other airlines that offer cheap prices include Southwest from $90 and Delta from $109 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.

See more FAQs

Traveling to a place near Florida Keys?

Book flights to Florida Keys if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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