$161+ Cheap flights from Midway (MDW) to Key West (EYW)
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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
Oct 5 — Oct 121
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 September 5, 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 September 5, 2026.
This Delta deal was found by Cheapflights users on 9/2. 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 11/1411:27 am -
1 stop7h 33m
Wed 11/186:05 pm -
1 stop5h 49m
Deal found 9/2![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 9/3. 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 9/266:05 am -
1 stop5h 48m
Fri 10/26:19 pm -
1 stop5h 25m
Deal found 9/3![Delta logo]()
$389
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 11/112:20 pm -
2 stops20h 59m
Fri 11/610:14 am -
1 stop10h 05m
Deal found 9/2![Multiple Airlines logo]()
$394
This Delta deal was found by Cheapflights users on 9/4. 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 12/1211:28 am -
1 stop7h 34m
Wed 12/166:06 pm -
1 stop5h 49m
Deal found 9/4![Delta logo]()
$406
This Delta deal was found by Cheapflights users on 9/2. 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 9/161:00 pm -
1 stop6h 00m
Tue 9/226:19 pm -
1 stop5h 25m
Deal found 9/2![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 9/2. 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 11/1011:27 am -
1 stop4h 43m
Sat 11/146:05 pm -
1 stop5h 49m
Deal found 9/2![Delta logo]()
$425
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 11/228:07 am -
2 stops27h 12m
Wed 11/2510:59 am -
1 stop9h 48m
Deal found 9/4![Multiple Airlines logo]()
$431
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 11/218:07 am -
2 stops11h 49m
Tue 11/2411:04 am -
1 stop9h 43m
Deal found 9/3![Multiple Airlines logo]()
$435
This Delta deal was found by Cheapflights users on 8/31. 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 12/1711:28 am -
1 stop4h 43m
Sun 12/206:20 pm -
1 stop5h 02m
Deal found 8/31![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 9/4. 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 11/1411:27 am -
1 stop7h 33m
Tue 11/176:05 pm -
1 stop5h 49m
Deal found 9/4![Delta logo]()
$439
This Kiwi.com deal was found by Cheapflights users on 8/31. 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.
Sat 12/55:20 pm -
2 stops15h 59m
Thu 12/1010:59 am -
1 stop9h 03m
Deal found 8/31![Multiple Airlines logo]()
$440
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 September 5, 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 September 5, 2026.
This Delta deal was found by Cheapflights users on 9/4. 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 11/1411:27 am -
1 stop7h 33m
Wed 11/186:05 pm -
1 stop5h 49m
Deal found 9/4![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 9/2. 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 9/161:00 pm -
1 stop6h 00m
Tue 9/226:19 pm -
1 stop5h 25m
Deal found 9/2![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 9/4. 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 11/1411:27 am -
1 stop7h 33m
Tue 11/176:05 pm -
1 stop5h 49m
Deal found 9/4![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 9/3. 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 9/161:00 pm -
1 stop6h 00m
Wed 9/236:19 pm -
1 stop5h 25m
Deal found 9/3![Delta logo]()
$455
This Delta deal was found by Cheapflights users on 9/3. 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 9/271:00 pm -
1 stop6h 00m
Tue 9/2911:42 am -
1 stop5h 33m
Deal found 9/3![Delta logo]()
$617
This Delta deal was found by Cheapflights users on 9/4. 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 10/41:00 pm -
1 stop6h 00m
Tue 10/66:10 pm -
1 stop5h 23m
Deal found 9/4![Delta logo]()
$637
This Delta deal was found by Cheapflights users on 8/31. 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 10/29:29 am -
2 stops9h 31m
Tue 10/611:51 am -
1 stop5h 23m
Deal found 8/31![Delta logo]()
$699
This Delta deal was found by Cheapflights users on 8/31. 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.
Tue 11/101:05 pm -
1 stop5h 55m
Sat 11/147:25 am -
2 stops10h 14m
Deal found 8/31![Delta logo]()
$699
Last-minute flights from Midway to Key WestDiscover last-minute flight deals from Midway to Key West. Data last updated September 5, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Key West. Data last updated September 5, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/3. 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 9/410:54 am -
1 stop5h 26m
Sun 9/611:48 am -
1 stop4h 56m
Deal found 9/3![Delta logo]()
$597
This Delta deal was found by Cheapflights users on 9/2. 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 9/161:00 pm -
1 stop6h 00m
Tue 9/226:19 pm -
1 stop5h 25m
Deal found 9/2![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 9/3. 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 9/161:00 pm -
1 stop6h 00m
Wed 9/236:19 pm -
1 stop5h 25m
Deal found 9/3![Delta logo]()
$455
This Delta deal was found by Cheapflights users on 9/2. 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 9/181:00 pm -
1 stop6h 00m
Tue 9/226:19 pm -
1 stop5h 25m
Deal found 9/2![Delta logo]()
$508
This Delta deal was found by Cheapflights users on 8/31. 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.
Tue 9/221:00 pm -
1 stop6h 00m
Mon 9/286:19 pm -
1 stop5h 25m
Deal found 8/31![Delta logo]()
$574
This Delta deal was found by Cheapflights users on 9/3. 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 9/2512:39 pm -
1 stop6h 21m
Wed 9/306:19 pm -
1 stop5h 25m
Deal found 9/3![Delta logo]()
$478
This Delta deal was found by Cheapflights users on 9/3. 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 9/266:05 am -
1 stop5h 48m
Fri 10/26:19 pm -
1 stop5h 25m
Deal found 9/3![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 9/3. 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 9/271:00 pm -
1 stop6h 00m
Fri 10/26:19 pm -
2 stops19h 20m
Deal found 9/3![Delta logo]()
$567
This Delta deal was found by Cheapflights users on 9/3. 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 9/2910:48 am -
1 stop5h 35m
Fri 10/26:19 pm -
2 stops15h 48m
Deal found 9/3![Delta logo]()
$507
This Delta deal was found by Cheapflights users on 8/31. 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 10/11:00 pm -
1 stop6h 00m
Mon 10/56:19 pm -
1 stop5h 25m
Deal found 8/31![Delta logo]()
$579
This Delta deal was found by Cheapflights users on 8/31. 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.
Tue 10/2712:49 pm -
1 stop6h 12m
Sat 10/314:00 pm -
1 stop7h 33m
Deal found 8/31![Delta logo]()
$568
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 September 5, 2026.
Search for one-way flight options from Midway to Key West. Find affordable one-way fares based on user searches. Data last updated September 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 11/176:16 am -
2 stops26h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Multiple Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 11/106:16 am -
2 stops26h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Multiple Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 11/239:29 am -
2 stops22h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Allegiant Air logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 10/146:21 am -
2 stops26h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Multiple Airlines logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 11/231:29 pm -
1 stop19h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Multiple Airlines logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 11/116:42 pm -
2 stops35h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Multiple Airlines logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 10/256:24 am -
2 stops28h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 9/116:25 am -
3 stops25h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$245
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 September 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $359 (Delta) |
One-way from | $161 (Kiwi.com) |
Popular in | November |
Cheapest in | July |
Average price | $543 |
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 7,457,451 searches. Data last updated September 5, 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 Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Tue 11/17
6:16 am-9:24 am
2 stops26h 08m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$161
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Tue 11/10
6:16 am-9:24 am
2 stops26h 08m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$172
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Wed 10/14
6:21 am-10:19 am
2 stops26h 58m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$188
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Fri 9/11
6:25 am-9:24 am
3 stops25h 59m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$245
Quickest round-trip
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Wed 11/11
11:27 am-5:10 pm
1 stop4h 43m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$309
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Tue 11/10
6:00 am-12:59 pm
1 stop5h 59m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$309
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Wed 10/14
6:04 am-12:53 pm
1 stop5h 49m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$309
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Sat 11/14
11:27 am-8:00 pm
1 stop7h 33m
Key West
Wed 11/18
6:05 pm-10:54 pm
1 stop5h 49m
$379
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Wed 9/16
1:00 pm-8:00 pm
1 stop6h 00m
Key West
Tue 9/22
6:19 pm-10:44 pm
1 stop5h 25m
$419
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Sat 11/14
11:27 am-8:00 pm
1 stop7h 33m
Key West
Tue 11/17
6:05 pm-10:54 pm
1 stop5h 49m
$439
Showing 1-10 of 15 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 September.
| 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.
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 September 5, 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.
Overall
7.8
Comfort
7.8
Food
7.2
Crew
8.5
Entertainment
7.8
Boarding
8.1
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Overall
7.8
Comfort
7.8
Food
7.2
Crew
8.5
Entertainment
7.8
Boarding
8.1
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Midway to Key West
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Complete your trip
Complete your trip to Key West by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Midway to Key West, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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 September 5, 2026.
Midway and Key West flights
Browse other Midway and Key West flight options. Last updated on September 5, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on September 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated September 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$294 | Average$499 | FlexibilityNo cancel fee | On-timeN/A |