$122+ 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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MDW
Nov 25 — Dec 21
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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Best
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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 October 26, 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 October 26, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/24. 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.
Thu 12/1710:59 am -
1 stop9h 31m
Thu 12/246:52 am -
2 stops28h 27m
Deal found 10/24![Multiple Airlines logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/2411:04 am -
1 stop9h 43m
Mon 11/308:42 pm -
1 stop12h 37m
Deal found 10/25![Multiple Airlines logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 10/24. 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.
Thu 12/1710:59 am -
1 stop9h 31m
Wed 12/301:11 pm -
2 stops20h 08m
Deal found 10/24![Multiple Airlines logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 10/24. 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.
Mon 12/2110:59 am -
1 stop9h 31m
Thu 12/241:11 pm -
2 stops22h 08m
Deal found 10/24![Multiple Airlines logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 10/24. 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.
Mon 12/2110:59 am -
1 stop9h 31m
Wed 12/301:11 pm -
2 stops20h 08m
Deal found 10/24![Multiple Airlines logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 10/24. 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.
Wed 12/1610:45 am -
2 stops12h 39m
Wed 12/308:35 pm -
1 stop12h 44m
Deal found 10/24![Multiple Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 10/24. 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.
Fri 12/1810:59 am -
1 stop9h 31m
Thu 12/241:11 pm -
2 stops22h 08m
Deal found 10/24![Multiple Airlines logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 10/24. 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.
Fri 12/1810:59 am -
1 stop9h 31m
Wed 12/301:11 pm -
2 stops20h 08m
Deal found 10/24![Multiple Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/2411:04 am -
1 stop9h 43m
Sat 11/288:42 pm -
1 stop12h 37m
Deal found 10/25![Multiple Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Wed 11/2510:59 am -
1 stop9h 48m
Mon 11/308:42 pm -
1 stop12h 37m
Deal found 10/25![Multiple Airlines logo]()
$340
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 October 26, 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 October 26, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/23. 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.
Fri 2/1910:59 am -
1 stop9h 43m
Mon 2/221:18 pm -
2 stops22h 18m
Deal found 10/23![Multiple Airlines logo]()
$423
This Delta deal was found by Cheapflights users on 10/21. 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 11/56:11 pm -
1 stop5h 22m
Mon 11/96:00 am -
1 stop5h 59m
Deal found 10/21![Delta logo]()
$514
This Delta deal was found by Cheapflights users on 10/23. 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 11/76:11 pm -
1 stop5h 22m
Wed 11/111:05 pm -
1 stop5h 55m
Deal found 10/23![Delta logo]()
$639
This Delta deal was found by Cheapflights users on 10/24. 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 12/216:22 pm -
1 stop5h 00m
Sun 12/276:00 am -
1 stop13h 57m
Deal found 10/24![Delta logo]()
$649
This Delta deal was found by Cheapflights users on 10/25. 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 11/267:30 am -
1 stop8h 45m
Mon 11/3011:27 am -
1 stop7h 33m
Deal found 10/25![Delta logo]()
$653
This Delta deal was found by Cheapflights users on 10/25. 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 11/267:30 am -
1 stop8h 45m
Sat 11/286:00 am -
1 stop10h 10m
Deal found 10/25![Delta logo]()
$658
This Delta deal was found by Cheapflights users on 10/25. 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 3/226:00 pm -
1 stop5h 10m
Thu 3/251:05 pm -
1 stop5h 38m
Deal found 10/25![Delta logo]()
$717
This Delta deal was found by Cheapflights users on 10/22. 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 12/236:20 pm -
1 stop5h 02m
Tue 12/2912:55 pm -
1 stop7h 03m
Deal found 10/22![Delta logo]()
$737
This Delta deal was found by Cheapflights users on 10/24. 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.
Fri 12/187:25 am -
1 stop5h 39m
Sun 12/2712:55 pm -
1 stop7h 02m
Deal found 10/24![Delta logo]()
$779
Last-minute flights from Key West to MidwayDiscover last-minute flight deals from Key West to Midway. Data last updated October 26, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to Midway. Data last updated October 26, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 10/25. 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 10/2911:51 am -
1 stop5h 23m
Sat 10/316:04 am -
1 stop7h 16m
Deal found 10/25![Delta logo]()
$584
This Delta deal was found by Cheapflights users on 10/21. 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 11/56:11 pm -
1 stop5h 22m
Mon 11/96:00 am -
1 stop5h 59m
Deal found 10/21![Delta logo]()
$514
This Delta deal was found by Cheapflights users on 10/23. 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 11/76:11 pm -
1 stop5h 22m
Wed 11/111:05 pm -
1 stop5h 55m
Deal found 10/23![Delta logo]()
$639
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/2411:04 am -
1 stop9h 43m
Mon 11/308:42 pm -
1 stop12h 37m
Deal found 10/25![Multiple Airlines logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/2411:04 am -
1 stop9h 43m
Sat 11/288:42 pm -
1 stop12h 37m
Deal found 10/25![Multiple Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/2411:04 am -
1 stop9h 43m
Sun 11/298:42 pm -
1 stop12h 37m
Deal found 10/25![Multiple Airlines logo]()
$356
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Wed 11/2510:59 am -
1 stop9h 48m
Mon 11/308:42 pm -
1 stop12h 37m
Deal found 10/25![Multiple Airlines logo]()
$340
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Wed 11/2510:59 am -
1 stop9h 48m
Sat 11/288:42 pm -
1 stop12h 37m
Deal found 10/25![Multiple Airlines logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Wed 11/2510:59 am -
1 stop9h 48m
Sun 11/298:42 pm -
1 stop12h 37m
Deal found 10/25![Multiple Airlines logo]()
$432
This Delta deal was found by Cheapflights users on 10/25. 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 11/267:30 am -
1 stop8h 45m
Mon 11/3011:27 am -
1 stop7h 33m
Deal found 10/25![Delta logo]()
$653
This Delta deal was found by Cheapflights users on 10/25. 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 11/267:30 am -
1 stop8h 45m
Sat 11/286:00 am -
1 stop10h 10m
Deal found 10/25![Delta logo]()
$658
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 October 26, 2026.
Search for one-way flight options from Key West to Midway. Find affordable one-way fares based on user searches. Data last updated October 26, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 1/2610:59 am -
2 stops13h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Multiple Airlines logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 10/24. 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.
Wed 11/1110:04 am -
2 stops8h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Multiple Airlines logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Wed 1/611:19 am -
2 stops30h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Multiple Airlines logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 10/24. 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.
Thu 11/1210:59 am -
2 stops13h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 11/101:16 pm -
2 stops29h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 10/24. 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.
Fri 11/1310:14 am -
1 stop5h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Allegiant Air logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 10/22. 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.
Wed 12/235:35 pm -
2 stops31h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 10/22. 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.
Thu 12/2410:59 am -
2 stops14h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/2411:04 am -
1 stop9h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 10/23. 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.
Mon 12/710:59 am -
1 stop7h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/2110:04 am -
2 stops47h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/2212:01 pm -
2 stops13h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$138
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 October 26, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $258 (Kiwi.com) |
One-way from | $122 (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 October 26, 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 Key West - MDW Chicago Midway
EYWMDW
Key West
Sat 11/14
10:04 am-11:47 pm
2 stops14h 43m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$126
Key WestChicago
EYW Key West - MDW Chicago Midway
EYWMDW
Key West
Mon 12/7
10:59 am-5:16 pm
1 stop7h 17m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$135
Key WestChicago
EYW Key West - MDW Chicago Midway
EYWMDW
Key West
Thu 12/3
7:22 pm-4:07 pm
2 stops21h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$141
Key WestChicago
EYW Key West - MDW Chicago Midway
EYWMDW
Key West
Sun 12/20
10:59 am-12:01 am
2 stops14h 02m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
Key WestChicago
EYW Key West - MDW Chicago Midway
EYWMDW
Key West
Mon 1/4
12:59 pm-4:26 pm
2 stops28h 27m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$170
Key WestChicago
EYW Key West - MDW Chicago Midway
EYWMDW
Key West
Mon 2/8
10:59 am-11:46 pm
2 stops13h 47m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$197
Key WestChicago
EYW Key West - MDW Chicago Midway
EYWMDW
Key West
Mon 11/23
11:59 am-7:47 pm
2 stops32h 48m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$210
Key WestChicago
EYW Key West - MDW Chicago Midway
EYWMDW
Key West
Sun 1/31
3:25 pm-11:46 pm
3 stops57h 21m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$221
Quickest round-trip
Key WestChicago
EYW Key West - MDW Chicago Midway
EYWMDW
Key West
Wed 1/6
6:00 pm-10:10 pm
1 stop5h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$227
Key WestChicago
EYW Key West - MDW Chicago Midway
EYWMDW
Key West
Fri 2/19
10:59 am-7:42 pm
1 stop9h 43m
Chicago Midway
Mon 2/22
1:18 pm-12:36 pm
2 stops22h 18m
$423
Showing 1-10 of 18 resultsSorted 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
Browse thousands of different options on Cheapflights for your next trip
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