$180+ Cheap flights from Key West (EYW) to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MDW
Oct 10 — Oct 171
Round-trip
1 adult, Economy
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Find cheap flights from Key West to Midway with Cheapflights
1. Tell us where you want to go
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Key West to Midway
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One-way
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 September 10, 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 September 10, 2026.
This Delta deal was found by Cheapflights users on 9/8. 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.
Sat 10/246:11 pm -
1 stop5h 22m
Mon 10/2612:49 pm -
1 stop6h 12m
Deal found 9/8![Delta logo]()
$406
This Delta deal was found by Cheapflights users on 9/7. 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.
Tue 9/226:19 pm -
1 stop5h 25m
Sat 9/2611:35 am -
1 stop7h 25m
Deal found 9/7![Delta logo]()
$439
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Tue 12/225:20 pm -
1 stop26h 42m
Mon 12/288:07 pm -
1 stop12h 11m
Deal found 9/5![Multiple Airlines logo]()
$515
This Delta deal was found by Cheapflights users on 9/8. 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.
Sat 9/124:35 pm -
1 stop7h 09m
Mon 9/1410:48 am -
1 stop5h 35m
Deal found 9/8![Delta logo]()
$530
This Delta deal was found by Cheapflights users on 9/8. 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.
Thu 9/247:40 am -
1 stop5h 14m
Mon 9/289:59 am -
2 stops9h 01m
Deal found 9/8![Delta logo]()
$829
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 September 10, 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 September 10, 2026.
This Delta deal was found by Cheapflights users on 9/5. 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 2/116:00 pm -
1 stop5h 10m
Mon 2/156:00 am -
1 stop6h 08m
Deal found 9/5![Delta logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Tue 12/225:20 pm -
2 stops20h 39m
Mon 12/288:07 pm -
1 stop12h 11m
Deal found 9/5![Multiple Airlines logo]()
$516
This Delta deal was found by Cheapflights users on 9/8. 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.
Sat 10/246:11 pm -
1 stop5h 22m
Mon 10/2612:49 pm -
1 stop6h 12m
Deal found 9/8![Delta logo]()
$406
This Delta deal was found by Cheapflights users on 9/7. 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.
Tue 9/226:19 pm -
1 stop5h 25m
Sat 9/2611:35 am -
1 stop7h 25m
Deal found 9/7![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 9/8. 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.
Thu 9/247:40 am -
1 stop5h 14m
Mon 9/281:00 pm -
1 stop6h 00m
Deal found 9/8![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 9/5. 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.
Tue 12/227:15 am -
2 stops11h 09m
Mon 12/289:30 am -
2 stops10h 28m
Deal found 9/5![Delta logo]()
$1,429
Last-minute flights from Key West to MidwayDiscover last-minute flight deals from Key West to Midway. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to Midway. Data last updated September 10, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/8. 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.
Sat 9/124:35 pm -
1 stop7h 09m
Mon 9/1410:48 am -
1 stop5h 35m
Deal found 9/8![Delta logo]()
$530
This Delta deal was found by Cheapflights users on 9/7. 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.
Tue 9/226:19 pm -
1 stop5h 25m
Sat 9/2611:35 am -
1 stop7h 25m
Deal found 9/7![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 9/8. 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.
Thu 9/247:40 am -
1 stop5h 14m
Mon 9/289:59 am -
2 stops9h 01m
Deal found 9/8![Delta logo]()
$829
This Delta deal was found by Cheapflights users on 9/8. 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.
Sat 10/246:11 pm -
1 stop5h 22m
Mon 10/2612:49 pm -
1 stop6h 12m
Deal found 9/8![Delta logo]()
$406
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 September 10, 2026.
Search for one-way flight options from Key West to Midway. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Sun 10/118:41 pm -
2 stops28h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$180
This Delta deal was found by Cheapflights users on 9/7. 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.
Tue 9/297:40 am -
1 stop5h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Delta logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Sun 1/33:10 pm -
2 stops22h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$375
This Delta deal was found by Cheapflights users on 9/8. 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.
Mon 10/196:10 pm -
1 stop23h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Delta logo]()
$392
This Delta deal was found by Cheapflights users on 9/9. 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.
Sun 10/116:10 pm -
1 stop5h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Delta logo]()
$430
This Delta deal was found by Cheapflights users on 9/8. 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.
Mon 11/96:05 pm -
1 stop5h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Delta logo]()
$440
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Sat 1/25:35 pm -
2 stops23h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$488
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 September 10, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $379 (Delta) |
One-way from | $180 (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 7,457,451 searches. Data last updated September 10, 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
Quickest round-trip
Key WestChicago
EYW Key West - MDW Chicago Midway
EYWMDW
Key West
Tue 9/29
7:40 am-11:54 am
1 stop5h 14m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$319
Key WestChicago
EYW Key West - MDW Chicago Midway
EYWMDW
Key West
Mon 10/5
11:42 am-4:11 pm
1 stop5h 29m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$319
Key WestChicago
EYW Key West - MDW Chicago Midway
EYWMDW
Key West
Thu 2/11
6:00 pm-10:10 pm
1 stop5h 10m
Chicago Midway
Mon 2/15
6:00 am-1:08 pm
1 stop6h 08m
$379
Key WestChicago
EYW Key West - MDW Chicago Midway
EYWMDW
Key West
Sat 10/24
6:11 pm-10:33 pm
1 stop5h 22m
Chicago Midway
Mon 10/26
12:49 pm-8:01 pm
1 stop6h 12m
$406
Key WestChicago
EYW Key West - MDW Chicago Midway
EYWMDW
Key West
Tue 9/22
6:19 pm-10:44 pm
1 stop5h 25m
Chicago Midway
Sat 9/26
11:35 am-8:00 pm
1 stop7h 25m
$439
Key WestChicago
EYW Key West - MDW Chicago Midway
EYWMDW
Key West
Thu 9/24
7:40 am-11:54 am
1 stop5h 14m
Chicago Midway
Mon 9/28
1:00 pm-8:00 pm
1 stop6h 00m
$439
Key WestChicago
EYW Key West - MDW Chicago Midway
EYWMDW
Key West
Mon 11/9
6:05 pm-10:54 pm
1 stop5h 49m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$440
Key WestChicago
EYW Key West - MDW Chicago Midway
EYWMDW
Key West
Sat 1/2
5:35 pm-4:15 pm
2 stops23h 40m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$488
Key WestChicago
EYW Key West - MDW Chicago Midway
EYWMDW
Key West
Tue 12/22
5:20 pm-12:59 pm
2 stops20h 39m
Chicago Midway
Mon 12/28
8:07 pm-9:18 am
1 stop12h 11m
$516
Key WestChicago
EYW Key West - MDW Chicago Midway
EYWMDW
Key West
Tue 12/22
7:15 am-5:24 pm
2 stops11h 09m
Chicago Midway
Mon 12/28
9:30 am-8:58 pm
2 stops10h 28m
$1,429
Sorted by cheapest first
- Most accurate provider: When it comes to deals on Key West-Chicago Midway Airport flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Key West-Chicago Midway Airport flight deals on Cheapflights vs. Expedia <90% 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 Expedia the most. Expedia 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 locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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