$159+ 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 7/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
Jul 8 — Jul 151
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 June 8, 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 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 7/122:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Thu 7/1612:05 pm
EYW
- MDW
2 stops10h 58m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 6/3. 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 7/2911:05 am
MDW
- EYW
1 stop7h 46m
Delta
Wed 8/56:15 pm
EYW
- MDW
1 stop5h 21m
Delta
Deal found 6/3![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 6/8. 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 6/8![Delta logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 7/52:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Sun 7/1212:05 pm
EYW
- MDW
2 stops27h 33m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 6/3. 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.
Thu 7/92:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Mon 7/1312:07 pm
EYW
- MDW
2 stops24h 00m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$350
This Delta deal was found by Cheapflights users on 6/3. 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.
Thu 7/2311:05 am
MDW
- EYW
1 stop7h 46m
Delta
Mon 7/276:18 pm
EYW
- MDW
1 stop4h 57m
Delta
Deal found 6/3![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 6/8. 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
MDW
- EYW
1 stop5h 21m
Delta
Wed 9/96:00 pm
EYW
- MDW
1 stop4h 46m
Delta
Deal found 6/8![Delta logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/112:44 pm
EYW
- MDW
2 stops24h 14m
Allegiant Air
Deal found 6/8![Allegiant Air logo]()
$365
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 7/510:55 am
EYW
- MDW
1 stop28h 43m
Allegiant Air
Deal found 6/7![Allegiant Air logo]()
$374
This Kiwi.com deal was found by Cheapflights users on 6/6. 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 8/92:49 pm
MDW
- EYW
1 stop17h 52m
Multiple Airlines
Fri 8/141:11 pm
EYW
- MDW
2 stops21h 40m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$379
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 8, 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 8, 2026.
This Delta deal was found by Cheapflights users on 6/4. 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.
Thu 8/1312:46 pm
MDW
- EYW
1 stop6h 08m
Delta
Tue 8/186:15 pm
EYW
- MDW
1 stop5h 21m
Delta
Deal found 6/4![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 6/6. 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 8/16:00 am
MDW
- EYW
1 stop5h 09m
Delta
Tue 8/117:40 am
EYW
- MDW
1 stop5h 11m
Delta
Deal found 6/6![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 6/7. 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 12/11:05 pm
MDW
- EYW
1 stop5h 38m
Delta
Mon 12/76:00 pm
EYW
- MDW
1 stop5h 10m
Delta
Deal found 6/7![Delta logo]()
$404
This Delta deal was found by Cheapflights users on 6/4. 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.
Wed 9/231:00 pm
MDW
- EYW
1 stop5h 50m
Delta
Sun 9/276:19 pm
EYW
- MDW
1 stop5h 06m
Delta
Deal found 6/4![Delta logo]()
$629
This Delta deal was found by Cheapflights users on 6/3. 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 8/1112:46 pm
MDW
- EYW
1 stop6h 08m
Delta
Sat 8/1511:48 am
EYW
- MDW
1 stop4h 50m
Delta
Deal found 6/3![Delta logo]()
$629
This Delta deal was found by Cheapflights users on 6/6. 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 7/1311:05 am
MDW
- EYW
1 stop5h 18m
Delta
Thu 7/166:18 pm
EYW
- MDW
1 stop4h 57m
Delta
Deal found 6/6![Delta logo]()
$633
This Delta deal was found by Cheapflights users on 6/4. 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 8/89:24 am
MDW
- EYW
2 stops9h 30m
Delta
Wed 8/127:40 am
EYW
- MDW
1 stop5h 11m
Delta
Deal found 6/4![Delta logo]()
$634
This Delta deal was found by Cheapflights users on 6/8. 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 9/59:24 am
MDW
- EYW
2 stops9h 33m
Delta
Wed 9/96:00 pm
EYW
- MDW
1 stop4h 46m
Delta
Deal found 6/8![Delta logo]()
$644
This Delta deal was found by Cheapflights users on 6/7. 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 9/269:30 am
MDW
- EYW
2 stops9h 20m
Delta
Tue 9/297:40 am
EYW
- MDW
1 stop5h 15m
Delta
Deal found 6/7![Delta logo]()
$644
This Delta deal was found by Cheapflights users on 6/7. 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 9/1911:25 am
MDW
- EYW
1 stop4h 59m
Delta
Fri 9/257:40 am
EYW
- MDW
2 stops11h 31m
Delta
Deal found 6/7![Delta logo]()
$644
Last-minute flights from Midway to Key WestDiscover last-minute flight deals from Midway to Key West. Data last updated June 8, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Key West. Data last updated June 8, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 7/510:55 am
EYW
- MDW
1 stop28h 43m
Allegiant Air
Deal found 6/7![Allegiant Air logo]()
$374
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 7/52:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Sun 7/1212:05 pm
EYW
- MDW
2 stops27h 33m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/112:44 pm
EYW
- MDW
2 stops24h 14m
Allegiant Air
Deal found 6/8![Allegiant Air logo]()
$365
This Kiwi.com deal was found by Cheapflights users on 6/8. 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
Fri 7/1012:07 pm
EYW
- MDW
2 stops10h 56m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 6/8. 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
Mon 7/131:11 pm
EYW
- MDW
2 stops22h 56m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 6/3. 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.
Thu 7/92:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Mon 7/1312:07 pm
EYW
- MDW
2 stops24h 00m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 7/122:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Thu 7/1612:05 pm
EYW
- MDW
2 stops10h 58m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 6/3. 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.
Thu 7/2311:05 am
MDW
- EYW
1 stop7h 46m
Delta
Mon 7/276:18 pm
EYW
- MDW
1 stop4h 57m
Delta
Deal found 6/3![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 6/3. 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 7/2911:05 am
MDW
- EYW
1 stop7h 46m
Delta
Wed 8/56:15 pm
EYW
- MDW
1 stop5h 21m
Delta
Deal found 6/3![Delta logo]()
$329
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 8, 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 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/5. 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
Deal found 6/5![Allegiant Air logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 9/1512:03 pm
MDW
- EYW
2 stops20h 21m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 7/33:28 pm
MDW
- EYW
2 stops21h 26m
Allegiant Air
Deal found 6/4![Allegiant Air logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 6/3. 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.
Thu 7/22:48 pm
MDW
- EYW
1 stop17h 53m
Allegiant Air
Deal found 6/3![Allegiant Air logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 6/142:46 pm
MDW
- EYW
1 stop17h 55m
Allegiant Air
Deal found 6/5![Allegiant Air logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 6/3. 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 10/1012:03 pm
MDW
- EYW
2 stops21h 16m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 6/3. 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 7/411:59 am
MDW
- EYW
2 stops22h 26m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 6/6. 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 6/198:20 pm
MDW
- EYW
2 stops38h 05m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 6/6. 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 6/206:00 am
MDW
- EYW
2 stops30h 16m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 6/212:46 pm
MDW
- EYW
1 stop17h 55m
Allegiant Air
Deal found 6/4![Allegiant Air logo]()
$252
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 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $327 (Kiwi.com) |
One-way from | $159 (Kiwi.com) |
Popular in | November |
Cheapest in | July |
Average price | $435 |
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 8, 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
Thu 8/13
12:46 pm-7:54 pm
1 stop6h 08m
Key West
Tue 8/18
6:15 pm-10:36 pm
1 stop5h 21m
$329
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Sat 8/1
6:00 am-12:09 pm
1 stop5h 09m
Key West
Tue 8/11
7:40 am-11:51 am
1 stop5h 11m
$339
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Tue 12/1
1:05 pm-7:43 pm
1 stop5h 38m
Key West
Mon 12/7
6:00 pm-10:10 pm
1 stop5h 10m
$404
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Wed 9/23
1:00 pm-7:50 pm
1 stop5h 50m
Key West
Sun 9/27
6:19 pm-10:25 pm
1 stop5h 06m
$629
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Tue 8/11
12:46 pm-7:54 pm
1 stop6h 08m
Key West
Sat 8/15
11:48 am-3:38 pm
1 stop4h 50m
$629
Quickest round-trip
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Mon 7/13
11:05 am-5:23 pm
1 stop5h 18m
Key West
Thu 7/16
6:18 pm-10:15 pm
1 stop4h 57m
$633
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Sat 8/8
9:24 am-7:54 pm
2 stops9h 30m
Key West
Wed 8/12
7:40 am-11:51 am
1 stop5h 11m
$634
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Sat 9/5
9:24 am-7:57 pm
2 stops9h 33m
Key West
Wed 9/9
6:00 pm-9:46 pm
1 stop4h 46m
$644
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Sat 9/26
9:30 am-7:50 pm
2 stops9h 20m
Key West
Tue 9/29
7:40 am-11:55 am
1 stop5h 15m
$644
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Sat 9/19
11:25 am-5:24 pm
1 stop4h 59m
Key West
Fri 9/25
7:40 am-6:11 pm
2 stops11h 31m
$644
Showing 1-10 of 22 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 8, 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.
Food
7.2
Boarding
8.1
Overall
7.9
Crew
8.5
Comfort
7.8
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Food
7.2
Boarding
8.1
Overall
7.9
Crew
8.5
Comfort
7.8
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Related info for your journey
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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 June 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$294 | Average$508 | FlexibilityNo cancel fee | On-timeN/A |