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Midway

$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 3/16. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MDW
feb. 11 — feb. 181
mié. 2/11
mié. 2/18
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 enero 12, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$83
(Kiwi.com)

One-way from

$60
(Flightnetwork)
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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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 enero 12, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/1211:28 am
MIA
-
MDW
Nonstop3h 28m
Frontier
dom. 2/156:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Deal found 1/12$83
This Mytrip deal was found by Cheapflights users on 1/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/2611:28 am
MIA
-
MDW
Nonstop3h 28m
Frontier
jue. 3/56:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Deal found 1/12$84
This Super.com deal was found by Cheapflights users on 1/11. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 1/154:44 pm
MIA
-
MDW
Nonstop3h 25m
Frontier
lun. 1/197:20 pm
MDW
-
MIA
Nonstop3h 05m
Frontier
Deal found 1/11$106
This Frontier deal was found by Cheapflights users on 1/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/2512:10 pm
MIA
-
MDW
1 stop7h 57m
Frontier
dom. 3/16:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Deal found 1/12$108
This Super.com deal was found by Cheapflights users on 1/11. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 3/611:13 am
MIA
-
MDW
Nonstop3h 28m
Frontier
dom. 3/86:00 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Deal found 1/11$109
This Frontier deal was found by Cheapflights users on 1/11. 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.
jue. 3/1911:13 am
MIA
-
MDW
Nonstop3h 28m
Frontier
lun. 3/236:00 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Deal found 1/11$110
This CheapOair deal was found by Cheapflights users on 1/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/511:28 am
MIA
-
MDW
Nonstop3h 28m
Frontier
dom. 3/86:00 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Deal found 1/11$111
This Kiwi.com deal was found by Cheapflights users on 1/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/1911:28 am
MIA
-
MDW
Nonstop3h 28m
Frontier
dom. 2/229:04 pm
MDW
-
MIA
1 stop12h 24m
Frontier
Deal found 1/12$112
This Trip.com deal was found by Cheapflights users on 1/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/1211:28 am
MIA
-
MDW
Nonstop3h 28m
Frontier
jue. 2/196:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Deal found 1/12$113
This Kiwi.com deal was found by Cheapflights users on 1/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 1/301:06 pm
EYW
-
MDW
1 stop7h 46m
Multiple Airlines
dom. 2/11:00 pm
MDW
-
EYW
1 stop22h 26m
Multiple Airlines
Deal found 1/11$213
This Delta deal was found by Cheapflights users on 1/12. 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.
jue. 1/297:10 am
EYW
-
MDW
1 stop5h 49m
Delta
lun. 2/26:00 am
MDW
-
EYW
1 stop6h 48m
Delta
Deal found 1/12$319
This Delta deal was found by Cheapflights users on 1/12. 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.
vie. 1/306:06 pm
EYW
-
MDW
1 stop5h 16m
Delta
dom. 2/112:46 pm
MDW
-
EYW
1 stop5h 54m
Delta
Deal found 1/12$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 enero 12, 2026.
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

jue. 2/12

5:05 am-11:27 am

1 stop7h 22m

Chicago Midway

dom. 2/15

6:15 am-10:28 am

Nonstop3h 13m

$105

MiamiChicago

MIA - MDW

MIAMDW

Miami

vie. 1/30

7:09 pm-8:43 am

1 stop14h 34m

Chicago Midway

mar. 2/3

1:20 pm-12:26 pm

1 stop22h 06m

$174

MiamiChicago

MIA - MDW

MIAMDW

Miami

vie. 3/6

12:16 pm-7:47 pm

1 stop8h 31m

Chicago Midway

lun. 3/9

2:41 pm-12:47 am

1 stop9h 06m

$182

MiamiChicago

MIA - MDW

MIAMDW

Miami

vie. 1/23

5:30 am-11:45 am

1 stop7h 15m

Chicago Midway

lun. 1/26

5:01 pm-12:47 am

1 stop6h 46m

$188

MiamiChicago

MIA - MDW

MIAMDW

Miami

lun. 3/23

11:13 am-1:41 pm

Nonstop3h 28m

Chicago Midway

jue. 3/26

2:41 pm-12:47 am

1 stop9h 06m

$205

MiamiChicago

MIA - MDW

MIAMDW

Miami

jue. 2/12

6:50 am-1:50 pm

2 stops8h 00m

Chicago Midway

lun. 2/16

12:30 pm-4:30 pm

Nonstop3h 00m

$213

Key WestChicago

EYW - MDW

EYWMDW

Key West

vie. 1/30

1:06 pm-7:52 pm

1 stop7h 46m

Chicago Midway

dom. 2/1

1:00 pm-12:26 pm

1 stop22h 26m

$213

MiamiChicago

MIA - MDW

MIAMDW

Miami

mar. 3/10

6:30 am-8:45 am

Nonstop3h 15m

Chicago Midway

mié. 3/18

10:30 am-8:05 pm

1 stop8h 35m

$213

MiamiChicago

MIA - MDW

MIAMDW

Miami

sáb. 2/7

5:50 am-9:53 am

1 stop5h 03m

Chicago Midway

dom. 2/8

1:26 pm-10:03 pm

1 stop7h 37m

$217

MiamiChicago

MIA - MDW

MIAMDW

Miami

mié. 2/25

8:15 am-11:59 am

1 stop4h 44m

Chicago Midway

mié. 3/4

10:49 am-6:21 pm

1 stop6h 32m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/12

Showing 1-10 of 38 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.

Cheapflights Insights

Everything you need to know about your flight from Florida Keys to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

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 enero 12, 2026.
Get a feel of what it's like to fly with Southwest and Frontier from Florida Keys to Chicago Midway Airport by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,255 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

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
4,255 reviews
Southwest
8.0
Very good
4,255 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

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
5.7
Fair
3,057 reviews
Southwest
8.0
Very good
4,255 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

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.

  • How long is the flight from Florida Keys to Chicago Midway Airport?

    Airlines like Frontier and Delta fly from Florida Keys to Chicago Midway Airport in about 5h 16m. The time it takes to get you to your destination can typically vary by up to 2h 06m. The distance from Florida Keys to Chicago Midway Airport is about 1238 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $41 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.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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