$120+ 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 7/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
Jul 18 — Jul 251
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 June 18, 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 June 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Thu 8/132:49 pm
MDW
- EYW
1 stop17h 52m
Multiple Airlines
Sun 8/1612:05 pm
EYW
- MDW
2 stops10h 58m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 6/15. 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 7/302:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Wed 8/511:46 am
EYW
- MDW
2 stops11h 17m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 6/16. 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 7/2911:05 am
MDW
- EYW
1 stop7h 46m
Delta
Wed 8/56:15 pm
EYW
- MDW
1 stop5h 21m
Delta
Deal found 6/16![Delta logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 6/15. 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 7/232:48 pm
MDW
- EYW
1 stop17h 53m
Allegiant Air
Sun 7/268:48 pm
EYW
- MDW
2 stops18h 50m
Allegiant Air
Deal found 6/15![Allegiant Air logo]()
$336
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Sun 11/87:25 am
MDW
- EYW
2 stops25h 54m
Multiple Airlines
Fri 11/1310:14 am
EYW
- MDW
1 stop5h 12m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Sun 7/192:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Fri 7/241:11 pm
EYW
- MDW
2 stops22h 56m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Sun 7/52:48 pm
MDW
- EYW
1 stop17h 53m
Allegiant Air
Sat 7/252:44 pm
EYW
- MDW
2 stops24h 14m
Allegiant Air
Deal found 6/16![Allegiant Air logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Sat 7/1112:11 pm
MDW
- EYW
2 stops23h 37m
Multiple Airlines
Thu 7/1610:55 am
EYW
- MDW
1 stop28h 43m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$348
This Delta deal was found by Cheapflights users on 6/14. 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 10/311:25 am
MDW
- EYW
1 stop7h 25m
Delta
Sat 10/106:00 pm
EYW
- MDW
1 stop5h 10m
Delta
Deal found 6/14![Delta logo]()
$356
This Delta deal was found by Cheapflights users on 6/16. 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 8/512:46 pm
MDW
- EYW
1 stop6h 11m
Delta
Mon 8/106:15 pm
EYW
- MDW
1 stop5h 21m
Delta
Deal found 6/16![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 6/16. 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.
Sat 12/510:35 am
MDW
- EYW
1 stop5h 36m
Delta
Thu 12/106:00 pm
EYW
- MDW
1 stop5h 10m
Delta
Deal found 6/16![Delta logo]()
$384
This Delta deal was found by Cheapflights users on 6/15. 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.
Sat 8/156:05 am
MDW
- EYW
1 stop7h 47m
Delta
Thu 8/2011:48 am
EYW
- MDW
1 stop5h 27m
Delta
Deal found 6/15![Delta logo]()
$386
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 June 18, 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 June 18, 2026.
This Delta deal was found by Cheapflights users on 6/14. 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 7/2911:05 am
MDW
- EYW
1 stop7h 46m
Delta
Wed 8/56:15 pm
EYW
- MDW
1 stop5h 21m
Delta
Deal found 6/14![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 6/15. 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 8/1312:46 pm
MDW
- EYW
1 stop6h 11m
Delta
Tue 8/186:15 pm
EYW
- MDW
1 stop5h 21m
Delta
Deal found 6/15![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 6/13. 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 8/512:46 pm
MDW
- EYW
1 stop6h 11m
Delta
Mon 8/106:15 pm
EYW
- MDW
1 stop5h 21m
Delta
Deal found 6/13![Delta logo]()
$448
This Delta deal was found by Cheapflights users on 6/17. 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 8/512:46 pm
MDW
- EYW
1 stop6h 11m
Delta
Sun 8/97:40 am
EYW
- MDW
1 stop5h 11m
Delta
Deal found 6/17![Delta logo]()
$546
This Delta deal was found by Cheapflights users on 6/15. 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 8/512:46 pm
MDW
- EYW
1 stop6h 11m
Delta
Sat 8/811:48 am
EYW
- MDW
1 stop4h 50m
Delta
Deal found 6/15![Delta logo]()
$546
This Delta deal was found by Cheapflights users on 6/18. 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 8/1310:54 am
MDW
- EYW
1 stop5h 26m
Delta
Sun 8/167:40 am
EYW
- MDW
1 stop5h 11m
Delta
Deal found 6/18![Delta logo]()
$559
This Delta deal was found by Cheapflights users on 6/16. 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.
Tue 8/1112:46 pm
MDW
- EYW
1 stop6h 11m
Delta
Sat 8/1511:48 am
EYW
- MDW
1 stop4h 50m
Delta
Deal found 6/16![Delta logo]()
$619
This Delta deal was found by Cheapflights users on 6/17. 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 8/1910:54 am
MDW
- EYW
1 stop5h 26m
Delta
Wed 8/2611:48 am
EYW
- MDW
2 stops7h 45m
Delta
Deal found 6/17![Delta logo]()
$634
Last-minute flights from Midway to Key WestDiscover last-minute flight deals from Midway to Key West. Data last updated June 18, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Key West. Data last updated June 18, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 6/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/211:05 am
MDW
- EYW
1 stop7h 48m
Delta
Tue 7/711:50 am
EYW
- MDW
1 stop5h 25m
Delta
Deal found 6/16![Delta logo]()
$432
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Sun 7/52:48 pm
MDW
- EYW
1 stop17h 53m
Allegiant Air
Sat 7/252:44 pm
EYW
- MDW
2 stops24h 14m
Allegiant Air
Deal found 6/16![Allegiant Air logo]()
$345
This Delta deal was found by Cheapflights users on 6/17. 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 7/811:05 am
MDW
- EYW
1 stop5h 18m
Delta
Tue 7/146:18 pm
EYW
- MDW
1 stop4h 57m
Delta
Deal found 6/17![Delta logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 6/16. 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 7/92:48 pm
MDW
- EYW
1 stop17h 53m
Allegiant Air
Sun 7/1210:55 am
EYW
- MDW
1 stop28h 43m
Allegiant Air
Deal found 6/16![Allegiant Air logo]()
$442
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Sat 7/1112:11 pm
MDW
- EYW
2 stops23h 37m
Multiple Airlines
Thu 7/1610:55 am
EYW
- MDW
1 stop28h 43m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Sun 7/192:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Fri 7/241:11 pm
EYW
- MDW
2 stops22h 56m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 6/15. 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 7/232:48 pm
MDW
- EYW
1 stop17h 53m
Allegiant Air
Sun 7/268:48 pm
EYW
- MDW
2 stops18h 50m
Allegiant Air
Deal found 6/15![Allegiant Air logo]()
$336
This Delta deal was found by Cheapflights users on 6/16. 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 7/2911:05 am
MDW
- EYW
1 stop7h 46m
Delta
Wed 8/56:15 pm
EYW
- MDW
1 stop5h 21m
Delta
Deal found 6/16![Delta logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 6/15. 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 7/302:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Wed 8/511:46 am
EYW
- MDW
2 stops11h 17m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 6/15. 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 7/3011:05 am
MDW
- EYW
1 stop5h 18m
Delta
Tue 8/46:15 pm
EYW
- MDW
1 stop5h 21m
Delta
Deal found 6/15![Delta logo]()
$394
This Kiwi.com deal was found by Cheapflights users on 6/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/302:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Sun 8/212:05 pm
EYW
- MDW
2 stops10h 58m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$419
This Delta deal was found by Cheapflights users on 6/13. 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 7/3011:05 am
MDW
- EYW
1 stop5h 18m
Delta
Thu 8/66:15 pm
EYW
- MDW
1 stop5h 21m
Delta
Deal found 6/13![Delta logo]()
$424
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 June 18, 2026.
Search for one-way flight options from Midway to Key West. Find affordable one-way fares based on user searches. Data last updated June 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Thu 7/232:48 pm
MDW
- EYW
1 stop17h 53m
Allegiant Air
Deal found 6/17![Allegiant Air logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Fri 7/312:04 pm
MDW
- EYW
2 stops45h 20m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 7/206:05 am
MDW
- EYW
2 stops29h 29m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Fri 7/39:15 pm
MDW
- EYW
3 stops41h 12m
Allegiant Air
Deal found 6/17![Allegiant Air logo]()
$259
This Delta deal was found by Cheapflights users on 6/17. 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.
Mon 7/2011:05 am
MDW
- EYW
1 stop5h 18m
Delta
Deal found 6/17![Delta logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Sun 6/212:46 pm
MDW
- EYW
1 stop17h 55m
Allegiant Air
Deal found 6/17![Allegiant Air logo]()
$310
This Delta deal was found by Cheapflights users on 6/15. 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 7/236:00 am
MDW
- EYW
1 stop6h 23m
Delta
Deal found 6/15![Delta logo]()
$337
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 June 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $325 (Kiwi.com) |
One-way from | $134 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $387 |
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 June 18, 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
Wed 7/29
11:05 am-7:51 pm
1 stop7h 46m
Key West
Wed 8/5
6:15 pm-10:36 pm
1 stop5h 21m
$329
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Thu 8/13
12:46 pm-7:57 pm
1 stop6h 11m
Key West
Tue 8/18
6:15 pm-10:36 pm
1 stop5h 21m
$329
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Wed 8/5
12:46 pm-7:57 pm
1 stop6h 11m
Key West
Mon 8/10
6:15 pm-10:36 pm
1 stop5h 21m
$448
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Wed 8/5
12:46 pm-7:57 pm
1 stop6h 11m
Key West
Sun 8/9
7:40 am-11:51 am
1 stop5h 11m
$546
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Wed 8/5
12:46 pm-7:57 pm
1 stop6h 11m
Key West
Sat 8/8
11:48 am-3:38 pm
1 stop4h 50m
$546
Quickest round-trip
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Thu 8/13
10:54 am-5:20 pm
1 stop5h 26m
Key West
Sun 8/16
7:40 am-11:51 am
1 stop5h 11m
$559
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Tue 8/11
12:46 pm-7:57 pm
1 stop6h 11m
Key West
Sat 8/15
11:48 am-3:38 pm
1 stop4h 50m
$619
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Wed 8/19
10:54 am-5:20 pm
1 stop5h 26m
Key West
Wed 8/26
11:48 am-6:33 pm
2 stops7h 45m
$634
Cheapest one-way
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Thu 7/23
2:48 pm-9:41 am
1 stop17h 53m
$120
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Mon 7/20
6:05 am-12:34 pm
2 stops29h 29m
$188
Showing 1-10 of 16 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 June.
| 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 June 18, 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.
Comfort
7.8
Entertainment
7.8
Overall
7.8
Boarding
8.1
Crew
8.5
Food
7.2
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Comfort
7.8
Entertainment
7.8
Overall
7.8
Boarding
8.1
Crew
8.5
Food
7.2
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.
Alternative routes
Complete your trip
Flights by cabin class
Key West flight routes
Other flight options
Other flights from Midway
Popular flights
Alternative routes for Midway to Key West
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
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 June 18, 2026.
Midway and Key West flights
Browse other Midway and Key West flight options. Last updated on June 18, 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 June 18, 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 2,558,603 searches. Data last updated June 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$294 | Average$508 | FlexibilityNo cancel fee | On-timeN/A |