$183+ 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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
Nov 13 — Nov 201
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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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 October 14, 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 October 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:08 am -
2 stops29h 28m
Fri 11/1310:14 am -
1 stop5h 12m
Deal found 10/14![Multiple Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 10/10. 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 12/73:50 pm -
2 stops17h 29m
Thu 12/1010:59 am -
1 stop10h 43m
Deal found 10/10![Multiple Airlines logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 10/10. 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 12/73:50 pm -
2 stops17h 29m
Fri 12/1110:59 am -
1 stop10h 43m
Deal found 10/10![Multiple Airlines logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 10/10. 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 12/43:50 pm -
2 stops17h 14m
Thu 12/1010:59 am -
1 stop10h 43m
Deal found 10/10![Multiple Airlines logo]()
$311
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1211:28 am -
1 stop7h 33m
Wed 12/166:06 pm -
1 stop5h 48m
Deal found 10/13![Delta logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 10/10. 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 12/63:50 pm -
2 stops17h 29m
Thu 12/1010:59 am -
1 stop10h 43m
Deal found 10/10![Multiple Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 10/10. 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 12/43:50 pm -
2 stops17h 14m
Fri 12/1110:59 am -
1 stop10h 43m
Deal found 10/10![Multiple Airlines logo]()
$335
This Kiwi.com deal was found by Cheapflights users on 10/10. 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 12/63:50 pm -
2 stops17h 29m
Fri 12/1110:59 am -
1 stop10h 43m
Deal found 10/10![Multiple Airlines logo]()
$341
This Delta deal was found by Cheapflights users on 10/10. 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
Wed 12/96:06 pm -
1 stop5h 48m
Deal found 10/10![Delta logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 10/10. 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 12/73:50 pm -
2 stops17h 29m
Mon 12/1410:59 am -
1 stop10h 43m
Deal found 10/10![Multiple Airlines logo]()
$355
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1311:27 am -
1 stop7h 33m
Thu 11/196:08 pm -
1 stop5h 46m
Deal found 10/14![Delta logo]()
$356
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 October 14, 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 October 14, 2026.
This Delta deal was found by Cheapflights users on 10/12. 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 1/196:00 am -
1 stop6h 08m
Tue 1/266:00 pm -
1 stop5h 10m
Deal found 10/12![Delta logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/268:07 pm -
1 stop13h 12m
Sun 1/310:59 am -
1 stop9h 03m
Deal found 10/14![Multiple Airlines logo]()
$755
This Delta deal was found by Cheapflights users on 10/10. 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 3/16:00 am -
1 stop6h 08m
Wed 3/316:00 pm -
1 stop5h 10m
Deal found 10/10![Delta logo]()
$406
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/218:07 pm -
1 stop13h 12m
Sat 1/25:35 pm -
2 stops14h 26m
Deal found 10/14![Multiple Airlines logo]()
$761
This Delta deal was found by Cheapflights users on 10/12. 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 1/79:30 am -
2 stops6h 41m
Thu 1/146:00 pm -
1 stop5h 10m
Deal found 10/12![Delta logo]()
$696
This Delta deal was found by Cheapflights users on 10/12. 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 1/169:30 am -
2 stops9h 13m
Sat 1/236:00 pm -
1 stop5h 10m
Deal found 10/12![Delta logo]()
$739
This Delta deal was found by Cheapflights users on 10/12. 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 11/1911:27 am -
1 stop4h 43m
Sun 11/226:08 pm -
1 stop5h 46m
Deal found 10/12![Delta logo]()
$758
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/209:30 am -
2 stops9h 13m
Sat 2/276:00 pm -
1 stop5h 10m
Deal found 10/13![Delta logo]()
$769
This Delta deal was found by Cheapflights users on 10/11. 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 1/29:30 am -
2 stops10h 28m
Wed 1/66:00 pm -
1 stop5h 10m
Deal found 10/11![Delta logo]()
$799
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/19:29 am -
2 stops9h 32m
Thu 11/56:11 pm -
1 stop5h 22m
Deal found 10/14![Delta logo]()
$847
Last-minute flights from Midway to Key WestDiscover last-minute flight deals from Midway to Key West. Data last updated October 14, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Key West. Data last updated October 14, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:08 am -
2 stops29h 28m
Fri 11/1310:14 am -
1 stop5h 12m
Deal found 10/14![Multiple Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:42 pm -
2 stops14h 37m
Fri 11/1310:14 am -
1 stop5h 12m
Deal found 10/14![Multiple Airlines logo]()
$370
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/111:05 pm -
1 stop5h 55m
Wed 11/186:08 pm -
1 stop5h 46m
Deal found 10/14![Delta logo]()
$416
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1311:27 am -
1 stop7h 33m
Wed 11/187:30 am -
1 stop5h 29m
Deal found 10/14![Delta logo]()
$313
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1311:27 am -
1 stop7h 33m
Thu 11/196:08 pm -
1 stop5h 46m
Deal found 10/14![Delta logo]()
$356
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1411:27 am -
1 stop7h 33m
Wed 11/186:08 pm -
1 stop5h 46m
Deal found 10/14![Delta logo]()
$376
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1411:27 am -
1 stop7h 33m
Thu 11/1911:43 am -
1 stop5h 35m
Deal found 10/14![Delta logo]()
$419
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 11/218:42 pm -
1 stop13h 36m
Tue 11/2411:04 am -
1 stop9h 43m
Deal found 10/11![Multiple Airlines logo]()
$394
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 11/221:16 pm -
2 stops22h 03m
Fri 11/2710:59 am -
1 stop9h 48m
Deal found 10/12![Multiple Airlines logo]()
$404
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 11/239:09 am -
2 stops23h 15m
Fri 11/2710:59 am -
1 stop9h 48m
Deal found 10/12![Multiple Airlines logo]()
$427
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 October 14, 2026.
Search for one-way flight options from Midway to Key West. Find affordable one-way fares based on user searches. Data last updated October 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:16 am -
2 stops29h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Multiple Airlines logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 10/10. 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 3/18:47 pm -
1 stop12h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Multiple Airlines logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 10/10. 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 12/109:37 pm -
3 stops35h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Multiple Airlines logo]()
$197
This Trip.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/288:42 pm -
1 stop12h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Multiple Airlines logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/19:23 pm -
2 stops18h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Multiple Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 10/10. 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 3/158:47 pm -
1 stop12h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Multiple Airlines logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/158:47 pm -
3 stops37h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Multiple Airlines logo]()
$255
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 October 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $266 (Kiwi.com) |
One-way from | $121 (Kiwi.com) |
Popular in | November |
Cheapest in | July |
Average price | $499 |
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 October 14, 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
Mon 11/2
6:16 am-12:36 pm
2 stops29h 20m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$183
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Thu 12/10
9:37 pm-10:04 am
3 stops35h 27m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$197
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Sat 11/28
8:42 pm-10:19 am
1 stop12h 37m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$201
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Mon 3/1
6:01 am-10:19 am
2 stops27h 18m
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 3/15
8:47 pm-10:19 am
1 stop12h 32m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$239
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Fri 1/15
8:47 pm-11:26 am
3 stops37h 39m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$255
Quickest round-trip
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Fri 1/1
6:00 am-1:55 pm
1 stop6h 55m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$278
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Tue 1/19
6:00 am-1:08 pm
1 stop6h 08m
Key West
Tue 1/26
6:00 pm-10:10 pm
1 stop5h 10m
$346
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Mon 3/1
6:00 am-1:08 pm
1 stop6h 08m
Key West
Wed 3/31
6:00 pm-10:10 pm
1 stop5h 10m
$406
ChicagoKey West
MDW Chicago Midway - EYW Key West
MDWEYW
Chicago Midway
Thu 1/7
9:30 am-5:11 pm
2 stops6h 41m
Key West
Thu 1/14
6:00 pm-10:10 pm
1 stop5h 10m
$696
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 October.
| 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 October 14, 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
Boarding
8.1
Food
7.2
Overall
7.8
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Boarding
8.1
Food
7.2
Overall
7.8
Entertainment
7.8
Crew
8.5
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.
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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
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 October 14, 2026.
Midway and Key West flights
Browse other Midway and Key West flight options. Last updated on October 14, 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 October 14, 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 October 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$294 | Average$483 | FlexibilityNo cancel fee | On-timeN/A |