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$90+ 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 7/2. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MDW
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheap flight deals from Florida Keys to Midway

Keep the following information in mind while searching for Florida Keys to Midway flight deals. Data was last updated May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$197
(Southwest)

One-way from

$90
(Southwest)

Popular in

March

Cheapest in

June

Average price

$406
Provider with most accurate pricing for Key West-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Key West-Chicago (CHI) flights.
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From Florida Keys to Chicago Midway
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One-way flight from Florida Keys to Chicago Midway
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Highest demand for flights based on searches. 17% potential increase in price ($81 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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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 May 1, 2025.

This Southwest deal was found by Cheapflights users on 4/30. 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 6/37:00 amMIA - MDW
Nonstop3h 10mSouthwest
Wed 6/45:10 pmMDW - MIA
Nonstop2h 55mSouthwest
Deal found 4/30$197
This eDestinos deal was found by Cheapflights users on 4/30. 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 5/297:24 pmMIA - MDW
1 stop25h 19mFrontier
Mon 6/27:05 amMDW - MIA
1 stop24h 00mFrontier
Deal found 4/30$205
This Delta deal was found by Cheapflights users on 4/30. 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 6/48:10 amMIA - MDW
1 stop4h 43mDelta
Tue 6/1712:44 pmMDW - MIA
1 stop7h 32mDelta
Deal found 4/30$217
This Delta deal was found by Cheapflights users on 4/28. 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 5/151:51 pmEYW - MDW
1 stop4h 52mDelta
Wed 5/2112:48 pmMDW - EYW
1 stop6h 19mDelta
Deal found 4/28$349

Cheapflights Fare Finder

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 May 1, 2025.
Use the filters below to find and compare flights from Florida Keys to Chicago Midway Airport that are best for you.

Fly from

Florida Keys

Fly to

Midway

Route

Depart

Return

Price

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 7/2

6:30 am-8:40 am

Nonstop3h 10m

Chicago Midway

Sat 7/5

7:10 pm-11:10 pm

Nonstop3h 00m

$179

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 5/29

7:24 pm-7:43 pm

1 stop25h 19m

Chicago Midway

Mon 6/2

7:05 am-8:05 am

1 stop24h 00m

$205

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 6/14

5:30 am-9:41 am

1 stop5h 11m

Chicago Midway

Tue 6/17

12:44 pm-9:16 pm

1 stop7h 32m

$217

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 5/15

1:51 pm-5:43 pm

1 stop4h 52m

Chicago Midway

Wed 5/21

12:48 pm-8:07 pm

1 stop6h 19m

$349

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 7/2

6:30 am-8:40 am

Nonstop3h 10m

$90

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 6/28

6:00 am-10:28 pm

1 stop17h 28m

$102

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 6/4

8:10 am-11:53 am

1 stop4h 43m

$109

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 6/19

2:45 pm-10:32 pm

1 stop8h 47m

$144

MiamiChicago

MIA - MDW

MIAMDW

Miami

Mon 5/5

8:58 am-8:19 am

1 stop24h 21m

$198

Key WestChicago

EYW - MDW

EYWMDW

Key West

Sun 6/29

7:10 am-11:59 am

1 stop5h 49m

$420

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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.

Cheapflights Insights

Everything you need to know about your flight from Florida Keys to Chicago Midway Airport

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 May 1, 2025.
Read through reviews of airlines operating flights from Florida Keys to Chicago, such as Southwest, Delta and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Frontier
6.0
Okay
3,287 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $90 on Southwest. Other airlines that offer cheap prices include Delta from $109 and Frontier from $116 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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