$112+ Cheap flights from Midway (MDW) to Key West (EYW)
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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
May 1 — May 81
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Key West 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 Midway to Key West
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Cheapest flights from Midway to Key WestExplore the most affordable flight options available from Midway to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 1, 2026.
Explore the most affordable flight options available from Midway to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 4/152:15 pm
MDW
- EYW
2 stops17h 51m
Multiple Airlines
Sun 4/199:46 am
EYW
- MDW
1 stop23h 18m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/22:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Thu 7/912:05 pm
EYW
- MDW
2 stops11h 06m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 7/52:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Thu 7/912:05 pm
EYW
- MDW
2 stops11h 06m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 7/22:48 pm
MDW
- EYW
1 stop17h 53m
Allegiant Air
Sun 7/58:48 pm
EYW
- MDW
2 stops18h 50m
Allegiant Air
Deal found 3/29![Allegiant Air logo]()
$328
This Delta deal was found by Cheapflights users on 3/30. 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.
Thu 4/2312:52 pm
MDW
- EYW
1 stop5h 48m
Delta
Wed 4/296:23 pm
EYW
- MDW
1 stop5h 05m
Delta
Deal found 3/30![Delta logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 6/42:46 pm
MDW
- EYW
1 stop16h 25m
Multiple Airlines
Sun 6/79:16 pm
EYW
- MDW
2 stops25h 46m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 6/42:46 pm
MDW
- EYW
1 stop16h 25m
Multiple Airlines
Mon 6/83:25 pm
EYW
- MDW
2 stops20h 47m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 8/62:49 pm
MDW
- EYW
1 stop17h 52m
Multiple Airlines
Mon 8/1012:07 pm
EYW
- MDW
2 stops11h 04m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 7/232:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Sun 7/268:48 pm
EYW
- MDW
2 stops18h 19m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$352
This Delta deal was found by Cheapflights users on 3/31. 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 9/76:00 am
MDW
- EYW
1 stop6h 09m
Delta
Wed 9/166:00 pm
EYW
- MDW
1 stop4h 46m
Delta
Deal found 3/31![Delta logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 4/135:30 am
MDW
- EYW
1 stop5h 56m
Multiple Airlines
Sun 4/199:46 am
EYW
- MDW
2 stops13h 33m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$355
Best flights from Midway to Key WestDiscover carefully curated flight deals from Midway to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 1, 2026.
Discover carefully curated flight deals from Midway to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 1, 2026.
This Delta deal was found by Cheapflights users on 3/27. 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 5/211:18 am
MDW
- EYW
1 stop7h 22m
Delta
Tue 5/127:30 am
EYW
- MDW
1 stop5h 26m
Delta
Deal found 3/27![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 3/27. 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 4/1712:52 pm
MDW
- EYW
1 stop5h 48m
Delta
Tue 4/216:23 pm
EYW
- MDW
1 stop5h 05m
Delta
Deal found 3/27![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 3/28. 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.
Tue 8/116:00 am
MDW
- EYW
1 stop6h 09m
Delta
Sat 8/156:00 pm
EYW
- MDW
1 stop4h 46m
Delta
Deal found 3/28![Delta logo]()
$474
This Delta deal was found by Cheapflights users on 3/29. 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 5/76:23 am
MDW
- EYW
1 stop5h 04m
Delta
Fri 5/86:19 pm
EYW
- MDW
1 stop22h 53m
Delta
Deal found 3/29![Delta logo]()
$497
This Delta deal was found by Cheapflights users on 3/27. 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 6/2311:05 am
MDW
- EYW
1 stop5h 24m
Delta
Sat 6/276:24 pm
EYW
- MDW
1 stop4h 53m
Delta
Deal found 3/27![Delta logo]()
$514
This Delta deal was found by Cheapflights users on 3/30. 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.
Sun 8/911:05 am
MDW
- EYW
1 stop7h 46m
Delta
Sat 8/156:00 pm
EYW
- MDW
1 stop4h 46m
Delta
Deal found 3/30![Delta logo]()
$529
This Delta deal was found by Cheapflights users on 3/31. 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 9/1110:35 am
MDW
- EYW
1 stop5h 39m
Delta
Tue 9/156:00 pm
EYW
- MDW
1 stop4h 46m
Delta
Deal found 3/31![Delta logo]()
$599
This Delta deal was found by Cheapflights users on 3/29. 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 7/2611:05 am
MDW
- EYW
1 stop7h 46m
Delta
Fri 7/316:18 pm
EYW
- MDW
1 stop4h 57m
Delta
Deal found 3/29![Delta logo]()
$607
This Delta deal was found by Cheapflights users on 3/27. 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 9/231:05 pm
MDW
- EYW
1 stop5h 40m
Delta
Sun 9/276:00 pm
EYW
- MDW
1 stop4h 46m
Delta
Deal found 3/27![Delta logo]()
$669
This Delta deal was found by Cheapflights users on 3/31. 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 7/96:05 am
MDW
- EYW
1 stop6h 24m
Delta
Sun 7/126:18 pm
EYW
- MDW
1 stop4h 57m
Delta
Deal found 3/31![Delta logo]()
$744
This Delta deal was found by Cheapflights users on 3/28. 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.
Sun 5/106:23 am
MDW
- EYW
1 stop5h 04m
Delta
Fri 5/1511:48 am
EYW
- MDW
1 stop5h 24m
Delta
Deal found 3/28![Delta logo]()
$868
Last-minute flights from Midway to Key WestDiscover last-minute flight deals from Midway to Key West. Data last updated April 1, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Key West. Data last updated April 1, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 3/28. 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 4/912:47 pm
MDW
- EYW
1 stop5h 54m
Delta
Tue 4/146:23 pm
EYW
- MDW
1 stop5h 05m
Delta
Deal found 3/28![Delta logo]()
$444
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 4/105:30 am
MDW
- EYW
1 stop5h 56m
Multiple Airlines
Sun 4/124:22 pm
EYW
- MDW
2 stops28h 45m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$441
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 4/135:30 am
MDW
- EYW
1 stop5h 56m
Multiple Airlines
Sun 4/199:46 am
EYW
- MDW
2 stops13h 33m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 4/152:15 pm
MDW
- EYW
2 stops17h 51m
Multiple Airlines
Sun 4/199:46 am
EYW
- MDW
1 stop23h 18m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$320
This Delta deal was found by Cheapflights users on 3/27. 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 4/1712:52 pm
MDW
- EYW
1 stop5h 48m
Delta
Tue 4/216:23 pm
EYW
- MDW
1 stop5h 05m
Delta
Deal found 3/27![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 3/30. 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.
Thu 4/2312:52 pm
MDW
- EYW
1 stop5h 48m
Delta
Wed 4/296:23 pm
EYW
- MDW
1 stop5h 05m
Delta
Deal found 3/30![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 3/28. 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.
Sat 4/256:00 am
MDW
- EYW
1 stop6h 44m
Delta
Tue 4/286:23 pm
EYW
- MDW
1 stop5h 05m
Delta
Deal found 3/28![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 3/31. 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 4/2910:41 am
MDW
- EYW
1 stop5h 42m
Delta
Sat 5/26:18 pm
EYW
- MDW
1 stop5h 10m
Delta
Deal found 3/31![Delta logo]()
$474
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 4/308:21 am
MDW
- EYW
1 stop27h 05m
Multiple Airlines
Sun 5/312:26 pm
EYW
- MDW
2 stops10h 53m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$487
One-way flights from Midway to Key WestSearch for one-way flight options from Midway to Key West. Find affordable one-way fares based on user searches. Data last updated April 1, 2026.
Search for one-way flight options from Midway to Key West. Find affordable one-way fares based on user searches. Data last updated April 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/189:14 am
MDW
- EYW
1 stop22h 52m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 5/186:00 am
MDW
- EYW
2 stops29h 34m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 4/166:00 am
MDW
- EYW
2 stops29h 26m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 5/179:16 am
MDW
- EYW
2 stops23h 55m
Allegiant Air
Deal found 3/27![Allegiant Air logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 5/179:16 am
MDW
- EYW
3 stops25h 11m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$287
This Delta deal was found by Cheapflights users on 3/31. 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 4/2312:52 pm
MDW
- EYW
1 stop5h 48m
Delta
Deal found 3/31![Delta logo]()
$294
Find flight deals from Midway to Key West
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Key West (EYW). 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 April 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $320 (Kiwi.com) |
One-way from | $112 (Kiwi.com) |
Popular in | November |
Cheapest in | May |
Average price | $588 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Key West 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 April 1, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Key West that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Sat 5/2
11:18 am-7:40 pm
1 stop7h 22m
Key West
Tue 5/12
7:30 am-11:56 am
1 stop5h 26m
$329
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Fri 4/17
12:52 pm-7:40 pm
1 stop5h 48m
Key West
Tue 4/21
6:23 pm-10:28 pm
1 stop5h 05m
$354
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Tue 8/11
6:00 am-1:09 pm
1 stop6h 09m
Key West
Sat 8/15
6:00 pm-9:46 pm
1 stop4h 46m
$474
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Thu 5/7
6:23 am-12:27 pm
1 stop5h 04m
Key West
Fri 5/8
6:19 pm-4:12 pm
1 stop22h 53m
$497
Quickest round-trip
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Tue 6/23
11:05 am-5:29 pm
1 stop5h 24m
Key West
Sat 6/27
6:24 pm-10:17 pm
1 stop4h 53m
$514
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Sun 8/9
11:05 am-7:51 pm
1 stop7h 46m
Key West
Sat 8/15
6:00 pm-9:46 pm
1 stop4h 46m
$529
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Fri 9/11
10:35 am-5:14 pm
1 stop5h 39m
Key West
Tue 9/15
6:00 pm-9:46 pm
1 stop4h 46m
$599
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Sun 7/26
11:05 am-7:51 pm
1 stop7h 46m
Key West
Fri 7/31
6:18 pm-10:15 pm
1 stop4h 57m
$607
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Wed 9/23
1:05 pm-7:45 pm
1 stop5h 40m
Key West
Sun 9/27
6:00 pm-9:46 pm
1 stop4h 46m
$669
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Thu 7/9
6:05 am-1:29 pm
1 stop6h 24m
Key West
Sun 7/12
6:18 pm-10:15 pm
1 stop4h 57m
$744
Showing 1-10 of 17 resultsSorted by cheapest first
Compare providers for flights from Midway to Key West
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 Midway to Key West in April.
| 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 Chicago Midway Airport-Key West flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Key West flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Key West flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Key West 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 Chicago Midway Airport-Key West 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 Midway to Key West
Have a flexible travel schedule? Discover the best time to fly to Key West from Midway with our price prediction graph.
MDW-EYW
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 Chicago Midway Airport to Key West
Reviews of airlines servicing Key West
Get insights into the airlines that provide service to Key West. 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 Key West. Reviews last updated April 1, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Key West, such as Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.8
Crew
8.5
Food
7.2
Overall
7.9
Boarding
8.1
Comfort
7.9
Reviews
1 / 20
2.0
MediocreJoseph,Aug 2023
MSP - MCO
Entertainment
7.8
Crew
8.5
Food
7.2
Overall
7.9
Boarding
8.1
Comfort
7.9
Reviews
1 / 20
2.0
MediocreJoseph,Aug 2023
MSP - MCO
Related info for your journey
Find useful and relevant information for your journey from Midway to Key West. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Midway to Key West
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Other flights to Key West
Explore flights to Key West departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on April 1, 2026.
Midway and Key West flights
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Other flights from Midway
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Top airline flying from Midway to Key West
Discover the top airline that operate flights from Midway to Key West. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$268 | Average$508 | FlexibilityNo cancel fee | On-timeN/A |