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$48+ 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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MDW
Nov 19 — Nov 261
1 adult
Tue 11/19
Tue 11/26
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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 November 14, 2024.

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 November 14, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 11/14. 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.
Fri 12/612:42 pmMIA - MDW
Nonstop3h 30mFrontier
Sun 12/157:25 amMDW - MIA
Nonstop3h 13mFrontier
Deal found 11/14$116
This eDestinos deal was found by Cheapflights users on 11/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2111:45 amMIA - MDW
1 stop12h 30mMultiple Airlines
Sat 11/236:48 pmMDW - MIA
1 stop14h 12mMultiple Airlines
Deal found 11/13$162
This Southwest deal was found by Cheapflights users on 11/12. 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 12/53:40 pmMIA - MDW
Nonstop3h 10mSouthwest
Tue 12/109:40 amMDW - MIA
Nonstop3h 05mSouthwest
Deal found 11/12$220
This Delta deal was found by Cheapflights users on 11/12. 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 12/76:00 amMIA - MDW
1 stop6h 58mDelta
Mon 12/99:30 amMDW - MIA
1 stop6h 33mDelta
Deal found 11/12$237
This Delta deal was found by Cheapflights users on 11/14. 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 12/266:02 pmEYW - MDW
1 stop5h 04mDelta
Wed 1/16:00 amMDW - EYW
1 stop5h 07mDelta
Deal found 11/14$287

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 2,752,363 searches. Data last updated November 14, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 1/17

11:50 am-2:19 pm

Nonstop3h 29m

Chicago Midway

Sun 1/19

7:25 am-11:37 am

Nonstop3h 12m

$115

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 12/5

8:06 am-6:12 pm

1 stop11h 06m

Chicago Midway

Sat 12/7

7:15 am-2:18 pm

2 stops30h 03m

$169

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 1/11

8:10 am-10:20 am

Nonstop3h 10m

Chicago Midway

Mon 1/13

6:10 pm-10:10 pm

Nonstop3h 00m

$178

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 12/7

6:00 am-11:58 am

1 stop6h 58m

Chicago Midway

Mon 12/9

9:30 am-5:03 pm

1 stop6h 33m

$237

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 12/26

6:02 pm-10:06 pm

1 stop5h 04m

Chicago Midway

Wed 1/1

6:00 am-12:07 pm

1 stop5h 07m

$287

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 12/6

12:42 pm-3:12 pm

Nonstop3h 30m

$58

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 1/11

8:10 am-10:20 am

Nonstop3h 10m

$79

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 2/11

6:20 pm-10:20 pm

1 stop5h 00m

$109

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 12/4

11:37 am-5:02 pm

1 stop6h 25m

$113

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 11/22

6:15 am-8:19 pm

2 stops15h 04m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 11 results
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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 November 14, 2024.
Read through reviews of airlines operating flights from Florida Keys to Chicago, such as Frontier, Southwest and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,045 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.3

Food

7.2

Crew

8.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.1
Very good
5,045 reviews
Southwest
8.1
Very good
5,045 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.3

Food

7.2

Crew

8.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Delta
8.0
Very good
8,788 reviews
Southwest
8.1
Very good
5,045 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.3

Food

7.2

Crew

8.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Frontier
6.1
Okay
3,551 reviews
Southwest
8.1
Very good
5,045 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.3

Food

7.2

Crew

8.7

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 $48 on Frontier. Other airlines that offer cheap prices include Southwest from $79 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, December is the cheapest month in which you can book a flight from Florida Keys to Chicago Midway Airport (average of $159). Flying from Florida Keys to Chicago Midway Airport in July is currently the most expensive (average of $231). 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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