$106+ 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 7/16. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
Jun 8 — Jun 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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Best
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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 May 9, 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 May 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 8/92:49 pm
MDW
- EYW
1 stop17h 52m
Multiple Airlines
Fri 8/1412:07 pm
EYW
- MDW
2 stops11h 01m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 8/92:49 pm
MDW
- EYW
1 stop17h 52m
Multiple Airlines
Tue 8/111:14 pm
EYW
- MDW
2 stops9h 54m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$323
This Delta deal was found by Cheapflights users on 5/6. 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.
Wed 6/310:59 am
MDW
- EYW
1 stop7h 50m
Delta
Tue 6/96:24 pm
EYW
- MDW
1 stop4h 53m
Delta
Deal found 5/6![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 5/8. 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.
Fri 8/712:46 pm
MDW
- EYW
1 stop6h 08m
Delta
Mon 8/106:15 pm
EYW
- MDW
1 stop5h 21m
Delta
Deal found 5/8![Delta logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Thu 7/302:48 pm
MDW
- EYW
1 stop17h 53m
Multiple Airlines
Sun 8/212:05 pm
EYW
- MDW
2 stops11h 03m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$347
This Delta deal was found by Cheapflights users on 5/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:53 pm
MDW
- EYW
1 stop5h 56m
Delta
Wed 6/106:24 pm
EYW
- MDW
1 stop4h 53m
Delta
Deal found 5/5![Delta logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Thu 6/252:46 pm
MDW
- EYW
1 stop17h 55m
Multiple Airlines
Sun 6/289:16 pm
EYW
- MDW
2 stops25h 55m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$356
This Delta deal was found by Cheapflights users on 5/8. 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 8/86:05 am
MDW
- EYW
1 stop7h 02m
Delta
Wed 8/127:40 am
EYW
- MDW
1 stop5h 11m
Delta
Deal found 5/8![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 5/7. 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 5/2610:59 am
MDW
- EYW
1 stop7h 50m
Delta
Tue 6/27:30 am
EYW
- MDW
1 stop5h 26m
Delta
Deal found 5/7![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 5/8. 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.
Tue 8/410:54 am
MDW
- EYW
1 stop5h 26m
Delta
Tue 8/116:15 pm
EYW
- MDW
2 stops19h 24m
Delta
Deal found 5/8![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 5/8. 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.
Wed 9/910:35 am
MDW
- EYW
1 stop5h 39m
Delta
Sun 9/136:00 pm
EYW
- MDW
1 stop4h 46m
Delta
Deal found 5/8![Delta logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 5/8. 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.
Thu 8/62:49 pm
MDW
- EYW
1 stop17h 52m
Multiple Airlines
Sun 8/912:05 pm
EYW
- MDW
2 stops11h 03m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$406
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 May 9, 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 May 9, 2026.
This Delta deal was found by Cheapflights users on 5/9. 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 6/512:53 pm
MDW
- EYW
1 stop5h 56m
Delta
Mon 6/86:24 pm
EYW
- MDW
1 stop4h 53m
Delta
Deal found 5/9![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 5/6. 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.
Fri 6/512:53 pm
MDW
- EYW
1 stop5h 56m
Delta
Fri 6/126:24 pm
EYW
- MDW
1 stop4h 53m
Delta
Deal found 5/6![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 5/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:00 am
MDW
- EYW
1 stop6h 29m
Delta
Sun 8/26:18 pm
EYW
- MDW
1 stop4h 57m
Delta
Deal found 5/5![Delta logo]()
$424
This Delta deal was found by Cheapflights users on 5/7. 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.
Wed 7/16:00 am
MDW
- EYW
1 stop5h 23m
Delta
Wed 7/86:18 pm
EYW
- MDW
1 stop4h 57m
Delta
Deal found 5/7![Delta logo]()
$461
This Delta deal was found by Cheapflights users on 5/9. 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 5/1512:53 pm
MDW
- EYW
1 stop5h 56m
Delta
Mon 5/187:30 am
EYW
- MDW
1 stop5h 26m
Delta
Deal found 5/9![Delta logo]()
$533
This Delta deal was found by Cheapflights users on 5/4. 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 7/26:00 am
MDW
- EYW
1 stop5h 23m
Delta
Sun 7/57:50 am
EYW
- MDW
1 stop5h 15m
Delta
Deal found 5/4![Delta logo]()
$539
This Delta deal was found by Cheapflights users on 5/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1410:59 am
MDW
- EYW
1 stop7h 50m
Delta
Sun 5/1711:48 am
EYW
- MDW
1 stop5h 24m
Delta
Deal found 5/5![Delta logo]()
$654
This Delta deal was found by Cheapflights users on 5/8. 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.
Fri 5/2210:59 am
MDW
- EYW
1 stop5h 24m
Delta
Mon 5/257:30 am
EYW
- MDW
1 stop5h 26m
Delta
Deal found 5/8![Delta logo]()
$849
Last-minute flights from Midway to Key WestDiscover last-minute flight deals from Midway to Key West. Data last updated May 9, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Key West. Data last updated May 9, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:23 am
MDW
- EYW
1 stop5h 04m
Delta
Tue 5/1911:48 am
EYW
- MDW
1 stop5h 24m
Delta
Deal found 5/5![Delta logo]()
$425
This Delta deal was found by Cheapflights users on 5/4. 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.
Fri 5/2210:59 am
MDW
- EYW
1 stop5h 24m
Delta
Wed 5/2711:48 am
EYW
- MDW
1 stop5h 24m
Delta
Deal found 5/4![Delta logo]()
$414
This Delta deal was found by Cheapflights users on 5/7. 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 5/2610:59 am
MDW
- EYW
1 stop7h 50m
Delta
Tue 6/27:30 am
EYW
- MDW
1 stop5h 26m
Delta
Deal found 5/7![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 5/8. 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.
Mon 6/110:59 am
MDW
- EYW
1 stop7h 50m
Delta
Tue 6/96:24 pm
EYW
- MDW
1 stop4h 53m
Delta
Deal found 5/8![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 5/6. 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.
Wed 6/310:59 am
MDW
- EYW
1 stop7h 50m
Delta
Tue 6/96:24 pm
EYW
- MDW
1 stop4h 53m
Delta
Deal found 5/6![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 5/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:53 pm
MDW
- EYW
1 stop5h 56m
Delta
Wed 6/106:24 pm
EYW
- MDW
1 stop4h 53m
Delta
Deal found 5/5![Delta logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 5/4. 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.
Thu 6/42:46 pm
MDW
- EYW
1 stop16h 25m
Multiple Airlines
Sun 6/711:04 am
EYW
- MDW
2 stops25h 05m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 5/6. 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.
Fri 6/512:53 pm
MDW
- EYW
1 stop5h 56m
Delta
Fri 6/126:24 pm
EYW
- MDW
1 stop4h 53m
Delta
Deal found 5/6![Delta logo]()
$407
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Thu 6/252:46 pm
MDW
- EYW
1 stop17h 55m
Multiple Airlines
Sun 6/289:16 pm
EYW
- MDW
2 stops25h 55m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$356
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 May 9, 2026.
Search for one-way flight options from Midway to Key West. Find affordable one-way fares based on user searches. Data last updated May 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/6. 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.
Thu 7/162:48 pm
MDW
- EYW
1 stop17h 53m
Allegiant Air
Deal found 5/6![Allegiant Air logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 5/2612:27 pm
MDW
- EYW
2 stops21h 39m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 6/112:46 pm
MDW
- EYW
1 stop17h 55m
Allegiant Air
Deal found 5/7![Allegiant Air logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Wed 5/2712:04 pm
MDW
- EYW
2 stops22h 21m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 7/173:28 pm
MDW
- EYW
2 stops41h 56m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 5/8. 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.
Wed 6/106:00 am
MDW
- EYW
3 stops50h 41m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 6/116:00 am
MDW
- EYW
2 stops31h 35m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 5/6. 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.
Mon 5/259:30 pm
MDW
- EYW
3 stops41h 52m
Allegiant Air
Deal found 5/6![Allegiant Air logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Wed 5/1312:04 pm
MDW
- EYW
2 stops22h 21m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 7/179:21 pm
MDW
- EYW
3 stops41h 06m
Allegiant Air
Deal found 5/6![Allegiant Air logo]()
$270
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 May 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $321 (Kiwi.com) |
One-way from | $106 (Kiwi.com) |
Popular in | November |
Cheapest in | May |
Average price | $342 |
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 May 9, 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
Fri 6/5
12:53 pm-7:49 pm
1 stop5h 56m
Key West
Mon 6/8
6:24 pm-10:17 pm
1 stop4h 53m
$329
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Fri 6/5
12:53 pm-7:49 pm
1 stop5h 56m
Key West
Fri 6/12
6:24 pm-10:17 pm
1 stop4h 53m
$407
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Wed 7/29
6:00 am-1:29 pm
1 stop6h 29m
Key West
Sun 8/2
6:18 pm-10:15 pm
1 stop4h 57m
$424
Quickest round-trip
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Wed 7/1
6:00 am-12:23 pm
1 stop5h 23m
Key West
Wed 7/8
6:18 pm-10:15 pm
1 stop4h 57m
$461
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Fri 5/15
12:53 pm-7:49 pm
1 stop5h 56m
Key West
Mon 5/18
7:30 am-11:56 am
1 stop5h 26m
$533
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Thu 7/2
6:00 am-12:23 pm
1 stop5h 23m
Key West
Sun 7/5
7:50 am-12:05 pm
1 stop5h 15m
$539
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Thu 5/14
10:59 am-7:49 pm
1 stop7h 50m
Key West
Sun 5/17
11:48 am-4:12 pm
1 stop5h 24m
$654
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Fri 5/22
10:59 am-5:23 pm
1 stop5h 24m
Key West
Mon 5/25
7:30 am-11:56 am
1 stop5h 26m
$849
Cheapest one-way
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Thu 7/16
2:48 pm-9:41 am
1 stop17h 53m
$106
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
Thu 6/11
6:00 am-2:35 pm
2 stops31h 35m
$198
Showing 1-10 of 18 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 May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Key West flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Key West flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Key West flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Key West flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Key West flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Midway to Key West
Have a flexible travel schedule? Discover the best time to fly to Key West from Midway with our price prediction graph.
MDW-EYW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to Key West
Reviews of airlines servicing Key West
Get insights into the airlines that provide service to Key West. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Key West. Reviews last updated May 9, 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
7.9
Boarding
8.1
Overall
7.9
Entertainment
7.8
Food
7.2
Crew
8.5
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Comfort
7.9
Boarding
8.1
Overall
7.9
Entertainment
7.8
Food
7.2
Crew
8.5
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$268 | Average$508 | FlexibilityNo cancel fee | On-timeN/A |