$107+ Cheap flights from Key West (EYW) 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MDW
Apr 12 — Apr 191
Round-trip
1 adult, Economy
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Key West to MidwayExplore the most affordable flight options available from Key West to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on März 13, 2026.
Explore the most affordable flight options available from Key West to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on März 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
Mi 4/2911:51 am
EYW
- MDW
1 stop20h 30m
Multiple Airlines
Sa 5/27:34 pm
MDW
- EYW
2 stops13h 47m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 3/9. 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.
Mi 4/296:23 pm
EYW
- MDW
1 stop5h 05m
Delta
Sa 5/211:18 am
MDW
- EYW
1 stop7h 22m
Delta
Deal found 3/9![Delta logo]()
$313
This Delta deal was found by Cheapflights users on 3/9. 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.
Fr 4/176:23 pm
EYW
- MDW
1 stop5h 05m
Delta
Mo 4/206:00 am
MDW
- EYW
1 stop6h 44m
Delta
Deal found 3/9![Delta logo]()
$333
This Delta deal was found by Cheapflights users on 3/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 11/46:00 pm
EYW
- MDW
1 stop4h 45m
Delta
Mi 11/251:05 pm
MDW
- EYW
1 stop5h 38m
Delta
Deal found 3/11![Delta logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
Do 4/99:46 am
EYW
- MDW
1 stop12h 35m
Multiple Airlines
Do 4/162:15 pm
MDW
- EYW
2 stops17h 54m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Do 3/269:46 am
EYW
- MDW
1 stop7h 06m
Multiple Airlines
Mo 3/309:51 pm
MDW
- EYW
2 stops12h 39m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 3/8. 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.
Mo 3/91:06 pm
EYW
- MDW
1 stop8h 47m
Multiple Airlines
Di 3/1011:19 am
MDW
- EYW
1 stop22h 52m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 3/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 3/2611:43 am
EYW
- MDW
1 stop6h 39m
Delta
Mo 3/3012:47 pm
MDW
- EYW
1 stop5h 54m
Delta
Deal found 3/11![Delta logo]()
$444
This Delta deal was found by Cheapflights users on 3/8. 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.
Do 4/96:25 pm
EYW
- MDW
1 stop5h 06m
Delta
Mo 4/136:00 am
MDW
- EYW
1 stop6h 44m
Delta
Deal found 3/8![Delta logo]()
$453
Best flights from Key West to MidwayDiscover carefully curated flight deals from Key West to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated März 13, 2026.
Discover carefully curated flight deals from Key West to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated März 13, 2026.
This Delta deal was found by Cheapflights users on 3/9. 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.
Mi 4/296:23 pm
EYW
- MDW
1 stop5h 05m
Delta
Sa 5/211:18 am
MDW
- EYW
1 stop7h 22m
Delta
Deal found 3/9![Delta logo]()
$313
This Delta deal was found by Cheapflights users on 3/9. 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.
Fr 4/176:23 pm
EYW
- MDW
1 stop5h 05m
Delta
Mo 4/206:00 am
MDW
- EYW
1 stop6h 44m
Delta
Deal found 3/9![Delta logo]()
$333
This Delta deal was found by Cheapflights users on 3/8. 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.
Do 4/96:25 pm
EYW
- MDW
1 stop5h 06m
Delta
Mo 4/136:00 am
MDW
- EYW
1 stop6h 44m
Delta
Deal found 3/8![Delta logo]()
$453
This Delta deal was found by Cheapflights users on 3/10. 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.
Do 4/96:25 pm
EYW
- MDW
1 stop5h 06m
Delta
Do 4/1612:52 pm
MDW
- EYW
1 stop5h 48m
Delta
Deal found 3/10![Delta logo]()
$659
This Delta deal was found by Cheapflights users on 3/9. 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.
Fr 4/246:23 pm
EYW
- MDW
1 stop5h 05m
Delta
So 4/269:27 am
MDW
- EYW
2 stops9h 13m
Delta
Deal found 3/9![Delta logo]()
$901
This Delta deal was found by Cheapflights users on 3/12. 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.
So 5/177:30 am
EYW
- MDW
1 stop5h 26m
Delta
Mi 5/206:23 am
MDW
- EYW
1 stop5h 04m
Delta
Deal found 3/12![Delta logo]()
$913
This Delta deal was found by Cheapflights users on 3/8. 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.
Do 4/96:25 pm
EYW
- MDW
1 stop5h 06m
Delta
Sa 4/1110:45 am
MDW
- EYW
1 stop5h 45m
Delta
Deal found 3/8![Delta logo]()
$928
Last-minute flights from Key West to MidwayDiscover last-minute flight deals from Key West to Midway. Data last updated März 13, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to Midway. Data last updated März 13, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
So 3/154:31 pm
EYW
- MDW
1 stop22h 50m
Multiple Airlines
Mo 3/239:51 pm
MDW
- EYW
2 stops12h 39m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$532
This Delta deal was found by Cheapflights users on 3/12. 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.
Di 3/176:25 pm
EYW
- MDW
1 stop5h 06m
Delta
Di 3/246:00 am
MDW
- EYW
1 stop6h 43m
Delta
Deal found 3/12![Delta logo]()
$500
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Do 3/269:46 am
EYW
- MDW
1 stop7h 06m
Multiple Airlines
Mo 3/309:51 pm
MDW
- EYW
2 stops12h 39m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$377
This Delta deal was found by Cheapflights users on 3/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 3/2611:43 am
EYW
- MDW
1 stop6h 39m
Delta
Mo 3/3012:47 pm
MDW
- EYW
1 stop5h 54m
Delta
Deal found 3/11![Delta logo]()
$444
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
Do 4/99:46 am
EYW
- MDW
1 stop12h 35m
Multiple Airlines
Do 4/162:15 pm
MDW
- EYW
2 stops17h 54m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$342
This Delta deal was found by Cheapflights users on 3/8. 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.
Do 4/96:25 pm
EYW
- MDW
1 stop5h 06m
Delta
Mo 4/136:00 am
MDW
- EYW
1 stop6h 44m
Delta
Deal found 3/8![Delta logo]()
$453
This Delta deal was found by Cheapflights users on 3/9. 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.
Fr 4/176:23 pm
EYW
- MDW
1 stop5h 05m
Delta
Mo 4/206:00 am
MDW
- EYW
1 stop6h 44m
Delta
Deal found 3/9![Delta logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
Mi 4/2911:51 am
EYW
- MDW
1 stop20h 30m
Multiple Airlines
Sa 5/27:34 pm
MDW
- EYW
2 stops13h 47m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 3/9. 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.
Mi 4/296:23 pm
EYW
- MDW
1 stop5h 05m
Delta
Sa 5/211:18 am
MDW
- EYW
1 stop7h 22m
Delta
Deal found 3/9![Delta logo]()
$313
One-way flights from Key West to MidwaySearch for one-way flight options from Key West to Midway. Find affordable one-way fares based on user searches. Data last updated März 13, 2026.
Search for one-way flight options from Key West to Midway. Find affordable one-way fares based on user searches. Data last updated März 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/8. 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.
Di 4/211:01 pm
EYW
- MDW
2 stops34h 13m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 3/12. 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.
Do 3/269:46 am
EYW
- MDW
1 stop7h 06m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Mo 6/12:51 pm
EYW
- MDW
2 stops24h 21m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Di 6/21:14 pm
EYW
- MDW
2 stops22h 55m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 3/12. 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.
Mo 3/301:06 pm
EYW
- MDW
1 stop27h 27m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 3/12. 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.
Mo 6/84:35 pm
EYW
- MDW
2 stops39h 25m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Mi 4/112:25 pm
EYW
- MDW
2 stops10h 54m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Sa 6/62:48 pm
EYW
- MDW
2 stops24h 08m
Allegiant Air
Deal found 3/11![Allegiant Air logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
So 6/79:16 pm
EYW
- MDW
2 stops34h 44m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$212
Find flight deals from Key West to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Key West (EYW) 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 März 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $217 (Kiwi.com) |
One-way from | $107 (Kiwi.com) |
Cheapflights Fare Finder
Customize your flight search to find flights from Key West 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 März 13, 2026.
Use the filters below to find and compare flights from Key West to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Key WestChicago
EYW - MDW
EYWMDW
Key West
Mi 4/29
6:23 pm-10:28 pm
1 stop5h 05m
Chicago Midway
Sa 5/2
11:18 am-7:40 pm
1 stop7h 22m
$313
Key WestChicago
EYW - MDW
EYWMDW
Key West
Fr 4/17
6:23 pm-10:28 pm
1 stop5h 05m
Chicago Midway
Mo 4/20
6:00 am-1:44 pm
1 stop6h 44m
$333
Key WestChicago
EYW - MDW
EYWMDW
Key West
Do 4/9
6:25 pm-10:31 pm
1 stop5h 06m
Chicago Midway
Mo 4/13
6:00 am-1:44 pm
1 stop6h 44m
$453
Key WestChicago
EYW - MDW
EYWMDW
Key West
Do 4/9
6:25 pm-10:31 pm
1 stop5h 06m
Chicago Midway
Do 4/16
12:52 pm-7:40 pm
1 stop5h 48m
$659
Key WestChicago
EYW - MDW
EYWMDW
Key West
Fr 4/24
6:23 pm-10:28 pm
1 stop5h 05m
Chicago Midway
So 4/26
9:27 am-7:40 pm
2 stops9h 13m
$901
Quickest round-trip
Key WestChicago
EYW - MDW
EYWMDW
Key West
So 5/17
7:30 am-11:56 am
1 stop5h 26m
Chicago Midway
Mi 5/20
6:23 am-12:27 pm
1 stop5h 04m
$913
Key WestChicago
EYW - MDW
EYWMDW
Key West
Do 4/9
6:25 pm-10:31 pm
1 stop5h 06m
Chicago Midway
Sa 4/11
10:45 am-5:30 pm
1 stop5h 45m
$928
Cheapest one-way
Key WestChicago
EYW - MDW
EYWMDW
Key West
Mi 4/1
12:25 pm-10:19 pm
2 stops10h 54m
$195
Quickest one-way
Key WestChicago
EYW - MDW
EYWMDW
Key West
Di 4/21
6:23 pm-10:28 pm
1 stop5h 05m
$274
Key WestChicago
EYW - MDW
EYWMDW
Key West
Di 6/2
2:05 pm-9:09 pm
1 stop8h 04m
$310
Showing 1-10 of 15 resultsSorted by cheapest first
Compare providers for flights from Key West to Midway
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Key West to Midway in March.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Key West-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Key West-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Key West-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Key West-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Key West-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Key West to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Key West with our price prediction graph.
EYW-MDW
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.
Related info for your journey
Find useful and relevant information for your journey from Key West to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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