$146+ 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 8/16. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
Sep 8 — Sep 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 August 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 August 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 11/612:03 pm -
2 stops20h 21m
Fri 11/1310:14 am -
1 stop5h 12m
Deal found 8/6![Multiple Airlines logo]()
$264
This Delta deal was found by Cheapflights users on 8/7. 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 9/161:00 pm -
1 stop6h 00m
Wed 9/236:19 pm -
1 stop5h 25m
Deal found 8/7![Delta logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 8/162:49 pm -
1 stop17h 52m
Fri 8/211:11 pm -
2 stops34h 36m
Deal found 8/4![Multiple Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 8/7. 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.
Fri 9/1111:35 am -
1 stop4h 48m
Sat 9/196:19 pm -
1 stop5h 25m
Deal found 8/7![Delta logo]()
$331
This Delta deal was found by Cheapflights users on 8/7. 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 12/511:28 am -
1 stop7h 34m
Thu 12/106:02 pm -
1 stop5h 54m
Deal found 8/7![Delta logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 8/162:49 pm -
1 stop17h 52m
Thu 8/2011:04 am -
2 stops12h 43m
Deal found 8/4![Multiple Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 8/8. 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 9/1211:35 am -
1 stop7h 25m
Sat 9/196:19 pm -
1 stop5h 25m
Deal found 8/8![Delta logo]()
$351
This Delta deal was found by Cheapflights users on 8/8. 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 9/210:54 am -
1 stop5h 26m
Wed 9/96:19 pm -
1 stop5h 25m
Deal found 8/8![Delta logo]()
$355
This Delta deal was found by Cheapflights users on 8/5. 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.
Mon 9/286:05 am -
1 stop5h 48m
Sat 10/36:19 pm -
1 stop5h 25m
Deal found 8/5![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 8/7. 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.
Mon 9/146:05 am -
1 stop5h 48m
Sat 9/196:19 pm -
1 stop5h 25m
Deal found 8/7![Delta logo]()
$361
This Delta deal was found by Cheapflights users on 8/5. 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.
Sat 8/226:11 am -
1 stop7h 41m
Fri 8/286:15 pm -
1 stop5h 21m
Deal found 8/5![Delta logo]()
$363
This Delta deal was found by Cheapflights users on 8/7. 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 12/1211:28 am -
1 stop7h 34m
Wed 12/166:02 pm -
1 stop5h 54m
Deal found 8/7![Delta logo]()
$366
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 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 August 9, 2026.
This Delta deal was found by Cheapflights users on 8/6. 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 9/161:00 pm -
1 stop6h 00m
Wed 9/236:19 pm -
1 stop5h 25m
Deal found 8/6![Delta logo]()
$323
This Delta deal was found by Cheapflights users on 8/5. 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.
Fri 8/2112:46 pm -
1 stop6h 11m
Thu 8/277:40 am -
1 stop5h 11m
Deal found 8/5![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 8/8. 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 9/911:35 am -
1 stop7h 25m
Sat 9/124:35 pm -
1 stop7h 09m
Deal found 8/8![Delta logo]()
$381
This Delta deal was found by Cheapflights users on 8/5. 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.
Sat 8/156:11 am -
1 stop7h 41m
Thu 8/207:40 am -
1 stop5h 11m
Deal found 8/5![Delta logo]()
$393
This Delta deal was found by Cheapflights users on 8/6. 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.
Thu 8/2712:46 pm -
1 stop6h 11m
Tue 9/16:15 pm -
1 stop5h 21m
Deal found 8/6![Delta logo]()
$554
This Delta deal was found by Cheapflights users on 8/6. 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.
Thu 10/812:45 pm -
1 stop6h 16m
Wed 10/147:40 am -
1 stop5h 10m
Deal found 8/6![Delta logo]()
$554
This Delta deal was found by Cheapflights users on 8/8. 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 8/2712:46 pm -
1 stop6h 11m
Mon 8/316:15 pm -
1 stop5h 21m
Deal found 8/8![Delta logo]()
$614
This Delta deal was found by Cheapflights users on 8/7. 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 9/129:29 am -
2 stops9h 31m
Sat 9/196:19 pm -
1 stop5h 25m
Deal found 8/7![Delta logo]()
$695
This Delta deal was found by Cheapflights users on 8/4. 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 9/2611:35 am -
1 stop7h 25m
Wed 9/307:40 am -
2 stops11h 39m
Deal found 8/4![Delta logo]()
$703
This Delta deal was found by Cheapflights users on 8/8. 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 10/3012:45 pm -
1 stop6h 16m
Tue 11/311:51 am -
2 stops7h 09m
Deal found 8/8![Delta logo]()
$703
Last-minute flights from Midway to Key WestDiscover last-minute flight deals from Midway to Key West. Data last updated August 9, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Key West. Data last updated August 9, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 8/162:49 pm -
1 stop17h 52m
Fri 8/211:11 pm -
2 stops34h 36m
Deal found 8/4![Multiple Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 8/162:49 pm -
1 stop17h 52m
Thu 8/2011:04 am -
2 stops12h 43m
Deal found 8/4![Multiple Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 8/5. 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.
Fri 8/2112:46 pm -
1 stop6h 11m
Thu 8/277:40 am -
1 stop5h 11m
Deal found 8/5![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 8/5. 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.
Sat 8/226:11 am -
1 stop7h 41m
Fri 8/286:15 pm -
1 stop5h 21m
Deal found 8/5![Delta logo]()
$363
This Delta deal was found by Cheapflights users on 8/8. 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 9/210:54 am -
1 stop5h 26m
Wed 9/96:19 pm -
1 stop5h 25m
Deal found 8/8![Delta logo]()
$355
This Delta deal was found by Cheapflights users on 8/7. 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.
Fri 9/1111:35 am -
1 stop4h 48m
Sat 9/196:19 pm -
1 stop5h 25m
Deal found 8/7![Delta logo]()
$331
This Delta deal was found by Cheapflights users on 8/7. 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.
Fri 9/116:05 am -
1 stop5h 48m
Thu 9/176:19 pm -
1 stop5h 26m
Deal found 8/7![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 8/8. 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 9/1211:35 am -
1 stop7h 25m
Sat 9/196:19 pm -
1 stop5h 25m
Deal found 8/8![Delta logo]()
$351
This Delta deal was found by Cheapflights users on 8/7. 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 9/1211:35 am -
1 stop7h 25m
Wed 9/166:19 pm -
1 stop5h 25m
Deal found 8/7![Delta logo]()
$381
This Delta deal was found by Cheapflights users on 8/7. 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.
Mon 9/146:05 am -
1 stop5h 48m
Sat 9/196:19 pm -
1 stop5h 25m
Deal found 8/7![Delta logo]()
$361
This Delta deal was found by Cheapflights users on 8/7. 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 9/161:00 pm -
1 stop6h 00m
Wed 9/236:19 pm -
1 stop5h 25m
Deal found 8/7![Delta logo]()
$323
This Delta deal was found by Cheapflights users on 8/5. 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.
Mon 9/286:05 am -
1 stop5h 48m
Sat 10/36:19 pm -
1 stop5h 25m
Deal found 8/5![Delta logo]()
$359
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 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 August 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 8/162:49 pm -
1 stop17h 52m
Deal found 8/8![Allegiant Air logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 8/8. 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.
Sat 10/106:40 am -
2 stops27h 41m
Deal found 8/8![Multiple Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 8/6. 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.
Wed 8/2611:50 am -
2 stops30h 23m
Deal found 8/6![Multiple Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 8/166:05 am -
2 stops53h 29m
Deal found 8/8![Multiple Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 8/8. 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.
Mon 10/121:26 pm -
3 stops42h 58m
Deal found 8/8![Multiple Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 8/8. 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 10/1011:33 am -
1 stop4h 42m
Deal found 8/8![Delta logo]()
$299
This Delta deal was found by Cheapflights users on 8/6. 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 8/2610:54 am -
1 stop5h 26m
Deal found 8/6![Delta logo]()
$384
This Delta deal was found by Cheapflights users on 8/8. 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 10/1212:45 pm -
1 stop6h 16m
Deal found 8/8![Delta logo]()
$470
This Delta deal was found by Cheapflights users on 8/5. 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.
Sat 9/199:29 am -
2 stops9h 31m
Deal found 8/5![Delta logo]()
$489
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 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $264 (Kiwi.com) |
One-way from | $146 (Kiwi.com) |
Popular in | November |
Cheapest in | June |
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 August 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 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
Quickest round-trip
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Fri 8/21
12:46 pm-7:57 pm
1 stop6h 11m
Key West
Thu 8/27
7:40 am-11:51 am
1 stop5h 11m
$369
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Wed 9/9
11:35 am-8:00 pm
1 stop7h 25m
Key West
Sat 9/12
4:35 pm-10:44 pm
1 stop7h 09m
$381
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Sat 8/15
6:11 am-2:52 pm
1 stop7h 41m
Key West
Thu 8/20
7:40 am-11:51 am
1 stop5h 11m
$393
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
$554
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Thu 10/8
12:45 pm-8:01 pm
1 stop6h 16m
Key West
Wed 10/14
7:40 am-11:50 am
1 stop5h 10m
$554
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
Mon 8/31
6:15 pm-10:36 pm
1 stop5h 21m
$614
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Sat 9/12
9:29 am-8:00 pm
2 stops9h 31m
Key West
Sat 9/19
6:19 pm-10:44 pm
1 stop5h 25m
$695
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Sat 9/26
11:35 am-8:00 pm
1 stop7h 25m
Key West
Wed 9/30
7:40 am-6:19 pm
2 stops11h 39m
$703
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Fri 10/30
12:45 pm-8:01 pm
1 stop6h 16m
Key West
Tue 11/3
11:51 am-6:00 pm
2 stops7h 09m
$703
Showing 1-10 of 17 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 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.
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Food
7.2
Crew
8.5
Overall
7.8
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Food
7.2
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.
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Complete your trip to Key West by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Midway to Key West, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Key West
Explore flights to Key West departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 9, 2026.
Midway and Key West flights
Browse other Midway and Key West flight options. Last updated on August 9, 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 9, 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 August 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$294 | Average$499 | FlexibilityNo cancel fee | On-timeN/A |