$138+ Cheap flights from Midway (MDW) to Key West (EYW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
Dec 5 — Dec 121
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 November 5, 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 November 5, 2026.
This Delta deal was found by Cheapflights users on 11/3. 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 12/11:02 pm -
1 stop5h 59m
Sat 12/56:06 pm -
1 stop5h 48m
Deal found 11/3![Delta logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Mon 12/146:11 pm -
1 stop15h 08m
Fri 12/1810:59 am -
1 stop9h 31m
Deal found 11/4![Multiple Airlines logo]()
$362
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 11/298:42 pm -
1 stop12h 37m
Fri 12/412:59 pm -
2 stops23h 34m
Deal found 11/1![Multiple Airlines logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/35:02 pm -
2 stops18h 17m
Mon 12/710:59 am -
1 stop7h 17m
Deal found 11/3![Multiple Airlines logo]()
$366
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/308:35 pm -
1 stop12h 44m
Fri 1/810:59 am -
1 stop9h 36m
Deal found 11/1![Multiple Airlines logo]()
$369
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 12/218:35 pm -
1 stop12h 44m
Fri 12/2510:59 am -
1 stop9h 11m
Deal found 10/31![Multiple Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 11/2. 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 33m
Thu 12/106:06 pm -
1 stop5h 48m
Deal found 11/2![Delta logo]()
$376
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/311:11 pm -
2 stops20h 08m
Mon 1/410:59 am -
1 stop9h 31m
Deal found 11/1![Multiple Airlines logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Wed 11/186:42 pm -
2 stops14h 37m
Tue 11/2411:04 am -
1 stop9h 43m
Deal found 11/3![Multiple Airlines logo]()
$378
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/308:35 pm -
1 stop12h 44m
Mon 1/1110:59 am -
1 stop9h 36m
Deal found 11/5![Multiple Airlines logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:08 am -
2 stops28h 13m
Sun 11/227:20 pm -
1 stop25h 27m
Deal found 11/2![Multiple Airlines logo]()
$382
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 November 5, 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 November 5, 2026.
This Delta deal was found by Cheapflights users on 11/2. 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 12/11:02 pm -
1 stop5h 59m
Sat 12/56:06 pm -
1 stop5h 48m
Deal found 11/2![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 11/1. 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 12/249:58 am -
1 stop6h 25m
Thu 12/316:22 pm -
1 stop5h 00m
Deal found 11/1![Delta logo]()
$459
This Delta deal was found by Cheapflights users on 11/2. 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 1/19:58 am -
1 stop6h 25m
Wed 1/65:00 pm -
1 stop6h 17m
Deal found 11/2![Delta logo]()
$475
This Delta deal was found by Cheapflights users on 11/4. 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 12/249:58 am -
1 stop6h 25m
Sun 12/276:22 pm -
1 stop5h 00m
Deal found 11/4![Delta logo]()
$519
This Delta deal was found by Cheapflights users on 11/3. 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.
Sat 12/1211:28 am -
1 stop7h 33m
Wed 12/167:25 am -
2 stops10h 25m
Deal found 11/3![Delta logo]()
$686
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/139:37 am -
2 stops9h 24m
Sat 12/266:23 pm -
1 stop4h 59m
Deal found 10/31![Delta logo]()
$729
This Delta deal was found by Cheapflights users on 10/31. 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 11/2011:20 am -
1 stop7h 40m
Tue 11/247:30 am -
1 stop5h 29m
Deal found 10/31![Delta logo]()
$799
This Delta deal was found by Cheapflights users on 11/3. 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 1/66:00 am -
1 stop6h 55m
Sun 1/105:00 pm -
1 stop6h 17m
Deal found 11/3![Delta logo]()
$859
This Delta deal was found by Cheapflights users on 10/31. 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 3/2210:35 am -
1 stop5h 36m
Mon 3/296:00 pm -
1 stop5h 10m
Deal found 10/31![Delta logo]()
$862
Last-minute flights from Midway to Key WestDiscover last-minute flight deals from Midway to Key West. Data last updated November 5, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Key West. Data last updated November 5, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Wed 11/186:42 pm -
2 stops14h 37m
Tue 11/2411:04 am -
1 stop9h 43m
Deal found 11/3![Multiple Airlines logo]()
$378
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:08 am -
2 stops28h 13m
Sun 11/227:20 pm -
1 stop25h 27m
Deal found 11/2![Multiple Airlines logo]()
$382
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 11/298:42 pm -
1 stop12h 37m
Fri 12/412:59 pm -
2 stops23h 34m
Deal found 11/1![Multiple Airlines logo]()
$364
This Delta deal was found by Cheapflights users on 11/3. 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 12/11:02 pm -
1 stop5h 59m
Sat 12/56:06 pm -
1 stop5h 48m
Deal found 11/3![Delta logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/35:02 pm -
2 stops18h 17m
Mon 12/710:59 am -
1 stop7h 17m
Deal found 11/3![Multiple Airlines logo]()
$366
This Delta deal was found by Cheapflights users on 11/2. 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 33m
Thu 12/106:06 pm -
1 stop5h 48m
Deal found 11/2![Delta logo]()
$376
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Mon 12/146:11 pm -
1 stop15h 08m
Fri 12/1810:59 am -
1 stop9h 31m
Deal found 11/4![Multiple Airlines logo]()
$362
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 12/218:35 pm -
1 stop12h 44m
Fri 12/2510:59 am -
1 stop9h 11m
Deal found 10/31![Multiple Airlines logo]()
$374
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/308:35 pm -
1 stop12h 44m
Fri 1/810:59 am -
1 stop9h 36m
Deal found 11/1![Multiple Airlines logo]()
$369
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/308:35 pm -
1 stop12h 44m
Mon 1/1110:59 am -
1 stop9h 36m
Deal found 11/5![Multiple Airlines logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/311:11 pm -
2 stops20h 08m
Mon 1/410:59 am -
1 stop9h 31m
Deal found 11/1![Multiple Airlines logo]()
$377
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 November 5, 2026.
Search for one-way flight options from Midway to Key West. Find affordable one-way fares based on user searches. Data last updated November 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 1/95:21 pm -
2 stops15h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Multiple Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 2/61:18 pm -
2 stops24h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 1/221:18 pm -
2 stops24h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 1/291:18 pm -
2 stops21h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Sat 12/191:11 pm -
2 stops24h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Mon 11/238:42 pm -
1 stop12h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 1/288:47 pm -
1 stop12h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 2/41:18 pm -
2 stops24h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$189
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 November 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $358 (Kiwi.com) |
One-way from | $138 (Kiwi.com) |
Popular in | December |
Cheapest in | February |
Average price | $403 |
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 7,457,451 searches. Data last updated November 5, 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
Fri 1/22
1:18 pm-3:17 pm
2 stops24h 59m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$144
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Fri 12/11
5:02 pm-10:19 am
2 stops40h 17m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$153
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Fri 1/29
8:47 pm-11:26 am
3 stops37h 39m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$185
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Fri 1/1
1:11 pm-10:19 am
3 stops44h 08m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$203
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Sat 11/21
8:42 pm-12:19 pm
3 stops38h 37m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$218
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Mon 11/23
1:16 pm-9:24 am
3 stops19h 08m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$238
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Sat 1/9
5:21 pm-3:35 pm
3 stops21h 14m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$250
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Fri 12/11
11:28 am-8:01 pm
1 stop7h 33m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$262
Quickest round-trip
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Thu 12/31
9:58 am-5:23 pm
1 stop6h 25m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$283
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Fri 11/20
1:06 pm-10:19 am
3 stops44h 13m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$284
Showing 1-10 of 20 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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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 November 5, 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
Overall
7.8
Crew
8.5
Food
7.2
Entertainment
7.8
Boarding
8.1
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Overall
7.8
Crew
8.5
Food
7.2
Entertainment
7.8
Boarding
8.1
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
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 November 5, 2026.
Midway and Key West flights
Browse other Midway and Key West flight options. Last updated on November 5, 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 November 5, 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 7,457,451 searches. Data last updated November 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$294 | Average$483 | FlexibilityNo cancel fee | On-timeN/A |