$132+ 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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
Sep 18 — Sep 251
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
Cheapest
Best
Last-minute
One-way
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 August 19, 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 August 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 10/136:15 am -
2 stops26h 09m
Fri 10/1610:14 am -
1 stop6h 26m
Deal found 8/16![Multiple Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 8/17. 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 8/17![Delta logo]()
$323
This Delta deal was found by Cheapflights users on 8/13. 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 9/911:35 am -
1 stop7h 25m
Tue 9/156:19 pm -
1 stop5h 25m
Deal found 8/13![Delta logo]()
$331
This Delta deal was found by Cheapflights users on 8/17. 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 12/511:28 am -
1 stop7h 34m
Tue 12/87:35 am -
1 stop5h 30m
Deal found 8/17![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 8/16. 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 9/1011:35 am -
1 stop7h 25m
Wed 9/166:19 pm -
1 stop5h 25m
Deal found 8/16![Delta logo]()
$358
This Delta deal was found by Cheapflights users on 8/13. 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 9/1011:35 am -
1 stop7h 25m
Tue 9/156:19 pm -
1 stop5h 25m
Deal found 8/13![Delta logo]()
$361
This Delta deal was found by Cheapflights users on 8/15. 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 9/210:54 am -
1 stop5h 26m
Sat 9/54:00 pm -
1 stop7h 36m
Deal found 8/15![Delta logo]()
$363
This Delta deal was found by Cheapflights users on 8/14. 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 12/511:28 am -
1 stop7h 34m
Sat 12/126:02 pm -
1 stop5h 54m
Deal found 8/14![Delta logo]()
$366
This Delta deal was found by Cheapflights users on 8/13. 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 9/610:56 am -
1 stop5h 24m
Thu 9/106:19 pm -
1 stop5h 25m
Deal found 8/13![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 8/15. 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 8/1812:46 pm -
1 stop6h 11m
Wed 9/26:15 pm -
1 stop5h 21m
Deal found 8/15![Delta logo]()
$387
This Delta deal was found by Cheapflights users on 8/16. 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 10/212:35 pm -
1 stop6h 25m
Sat 10/36:19 pm -
1 stop5h 25m
Deal found 8/16![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 8/14. 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 8/226:11 am -
1 stop5h 15m
Fri 8/287:40 am -
1 stop5h 11m
Deal found 8/14![Delta logo]()
$393
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 August 19, 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 August 19, 2026.
This Delta deal was found by Cheapflights users on 8/16. 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 8/16![Delta logo]()
$323
This Delta deal was found by Cheapflights users on 8/13. 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 9/610:56 am -
1 stop5h 24m
Thu 9/106:19 pm -
1 stop5h 25m
Deal found 8/13![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 8/17. 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 11/1011:28 am -
1 stop7h 34m
Sat 11/146:02 pm -
1 stop5h 54m
Deal found 8/17![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 8/14. 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 8/2712:46 pm -
1 stop6h 11m
Tue 9/16:15 pm -
1 stop5h 21m
Deal found 8/14![Delta logo]()
$448
This Delta deal was found by Cheapflights users on 8/15. 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 11/46:04 am -
1 stop7h 16m
Tue 11/106:02 pm -
1 stop5h 54m
Deal found 8/15![Delta logo]()
$458
This Delta deal was found by Cheapflights users on 8/14. 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 9/312:46 pm -
1 stop6h 11m
Sun 9/611:48 am -
1 stop4h 56m
Deal found 8/14![Delta logo]()
$488
This Delta deal was found by Cheapflights users on 8/17. 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 8/226:11 am -
1 stop7h 41m
Fri 8/2811:48 am -
1 stop5h 27m
Deal found 8/17![Delta logo]()
$490
This Delta deal was found by Cheapflights users on 8/15. 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 8/15![Delta logo]()
$546
This Delta deal was found by Cheapflights users on 8/16. 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 10/1810:59 am -
1 stop5h 16m
Fri 10/236:10 pm -
1 stop5h 23m
Deal found 8/16![Delta logo]()
$597
This Delta deal was found by Cheapflights users on 8/13. 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 9/56:05 am -
1 stop7h 47m
Tue 9/86:19 pm -
1 stop5h 25m
Deal found 8/13![Delta logo]()
$639
Last-minute flights from Midway to Key WestDiscover last-minute flight deals from Midway to Key West. Data last updated August 19, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Key West. Data last updated August 19, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/15. 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 8/1812:46 pm -
1 stop6h 11m
Wed 9/26:15 pm -
1 stop5h 21m
Deal found 8/15![Delta logo]()
$387
This Delta deal was found by Cheapflights users on 8/14. 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 8/226:11 am -
1 stop5h 15m
Fri 8/287:40 am -
1 stop5h 11m
Deal found 8/14![Delta logo]()
$393
This Delta deal was found by Cheapflights users on 8/18. 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 8/2712:46 pm -
1 stop6h 11m
Tue 9/16:15 pm -
1 stop5h 21m
Deal found 8/18![Delta logo]()
$448
This Delta deal was found by Cheapflights users on 8/14. 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 8/296:11 am -
1 stop7h 41m
Mon 8/316:15 pm -
1 stop5h 21m
Deal found 8/14![Delta logo]()
$482
This Delta deal was found by Cheapflights users on 8/15. 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 9/210:54 am -
1 stop5h 26m
Sat 9/54:00 pm -
1 stop7h 36m
Deal found 8/15![Delta logo]()
$363
This Delta deal was found by Cheapflights users on 8/14. 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 9/312:46 pm -
1 stop6h 11m
Sun 9/611:48 am -
1 stop4h 56m
Deal found 8/14![Delta logo]()
$488
This Delta deal was found by Cheapflights users on 8/14. 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 9/610:56 am -
1 stop5h 24m
Thu 9/1011:42 am -
1 stop4h 42m
Deal found 8/14![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 8/16. 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 9/911:35 am -
1 stop4h 48m
Wed 9/166:19 pm -
1 stop5h 25m
Deal found 8/16![Delta logo]()
$331
This Delta deal was found by Cheapflights users on 8/15. 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 9/1011:35 am -
1 stop7h 25m
Wed 9/166:19 pm -
1 stop5h 25m
Deal found 8/15![Delta logo]()
$358
This Delta deal was found by Cheapflights users on 8/14. 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 8/14![Delta logo]()
$323
This Delta deal was found by Cheapflights users on 8/18. 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
Fri 9/186:19 pm -
1 stop5h 25m
Deal found 8/18![Delta logo]()
$460
This Delta deal was found by Cheapflights users on 8/15. 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 9/231:00 pm -
1 stop6h 00m
Sat 9/266:19 pm -
1 stop5h 25m
Deal found 8/15![Delta logo]()
$450
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 August 19, 2026.
Search for one-way flight options from Midway to Key West. Find affordable one-way fares based on user searches. Data last updated August 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 9/266:25 am -
2 stops27h 56m
Deal found 8/18![Multiple Airlines logo]()
$132
This Delta deal was found by Cheapflights users on 8/16. 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 9/3010:48 am -
1 stop5h 35m
Deal found 8/16![Delta logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 10/112:54 pm -
3 stops43h 30m
Deal found 8/16![Multiple Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 11/187:25 am -
2 stops25h 54m
Deal found 8/15![Multiple Airlines logo]()
$181
This Delta deal was found by Cheapflights users on 8/18. 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 9/2611:35 am -
1 stop7h 25m
Deal found 8/18![Delta logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 11/301:29 pm -
1 stop19h 50m
Deal found 8/17![Multiple Airlines logo]()
$259
This Delta deal was found by Cheapflights users on 8/14. 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 9/286:05 am -
1 stop5h 48m
Deal found 8/14![Delta logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 12/3111:36 am -
2 stops28h 06m
Deal found 8/15![Multiple Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 8/14. 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 11/1911:28 am -
1 stop4h 39m
Deal found 8/14![Delta logo]()
$319
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 August 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $289 (Kiwi.com) |
One-way from | $162 (Delta) |
Popular in | November |
Cheapest in | July |
Average price | $328 |
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 August 19, 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
Wed 9/16
1:00 pm-8:00 pm
1 stop6h 00m
Key West
Wed 9/23
6:19 pm-10:44 pm
1 stop5h 25m
$323
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Sun 9/6
10:56 am-5:20 pm
1 stop5h 24m
Key West
Thu 9/10
6:19 pm-10:44 pm
1 stop5h 25m
$369
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Tue 11/10
11:28 am-8:02 pm
1 stop7h 34m
Key West
Sat 11/14
6:02 pm-10:56 pm
1 stop5h 54m
$399
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Thu 8/27
12:46 pm-7:57 pm
1 stop6h 11m
Key West
Tue 9/1
6:15 pm-10:36 pm
1 stop5h 21m
$448
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Wed 11/4
6:04 am-2:20 pm
1 stop7h 16m
Key West
Tue 11/10
6:02 pm-10:56 pm
1 stop5h 54m
$458
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Thu 9/3
12:46 pm-7:57 pm
1 stop6h 11m
Key West
Sun 9/6
11:48 am-3:44 pm
1 stop4h 56m
$488
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Sat 8/22
6:11 am-2:52 pm
1 stop7h 41m
Key West
Fri 8/28
11:48 am-4:15 pm
1 stop5h 27m
$490
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Tue 9/22
1:00 pm-8:00 pm
1 stop6h 00m
Key West
Mon 9/28
6:19 pm-10:44 pm
1 stop5h 25m
$546
Quickest round-trip
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Sun 10/18
10:59 am-5:15 pm
1 stop5h 16m
Key West
Fri 10/23
6:10 pm-10:33 pm
1 stop5h 23m
$597
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Sat 9/5
6:05 am-2:52 pm
1 stop7h 47m
Key West
Tue 9/8
6:19 pm-10:44 pm
1 stop5h 25m
$639
Showing 1-10 of 21 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 August.
| 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 August 19, 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
Comfort
7.8
Food
7.2
Boarding
8.1
Crew
8.5
Overall
7.8
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Entertainment
7.8
Comfort
7.8
Food
7.2
Boarding
8.1
Crew
8.5
Overall
7.8
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 to Key West by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Key West by cabin class
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 August 19, 2026.
Midway and Key West flights
Browse other Midway and Key West flight options. Last updated on August 19, 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 August 19, 2026.
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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 August 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$294 | Average$499 | FlexibilityNo cancel fee | On-timeN/A |