$212+ Cheap flights from Portland, ME to Key West (PWM - 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 5/22. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — EYW
Jun 5 — Jun 121
Round-trip
1 adult, Economy
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Find cheap flights from Portland 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
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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 Portland to Key West
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Best
Last-minute
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Cheapest flights from Portland to Key WestExplore the most affordable flight options available from Portland to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 6, 2026.
Explore the most affordable flight options available from Portland to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 6, 2026.
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.
Sat 6/66:26 pm
PWM
- EYW
1 stop15h 58m
Breeze Airways
Thu 6/1112:05 pm
EYW
- PWM
1 stop21h 07m
Breeze Airways
Deal found 5/5![Breeze Airways logo]()
$326
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.
Sun 6/73:11 pm
PWM
- EYW
1 stop27h 16m
Multiple Airlines
Fri 6/1212:07 pm
EYW
- PWM
1 stop21h 05m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$330
This Delta deal was found by Cheapflights users on 5/3. 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 6/306:00 am
PWM
- EYW
1 stop7h 43m
Delta
Fri 7/32:38 pm
EYW
- PWM
1 stop8h 27m
Delta
Deal found 5/3![Delta logo]()
$355
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/18:04 am
PWM
- EYW
1 stop5h 37m
American Airlines
Sat 6/65:07 pm
EYW
- PWM
1 stop5h 22m
American Airlines
Deal found 5/1![American Airlines logo]()
$357
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.
Sat 6/68:05 am
PWM
- EYW
2 stops11h 44m
Delta
Wed 6/102:28 pm
EYW
- PWM
1 stop8h 37m
Delta
Deal found 5/4![Delta logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Tue 9/14:44 pm
PWM
- EYW
2 stops18h 22m
Breeze Airways
Tue 9/81:14 pm
EYW
- PWM
1 stop28h 37m
Breeze Airways
Deal found 5/1![Breeze Airways logo]()
$364
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:02 am
PWM
- EYW
2 stops9h 37m
American Airlines
Sat 11/141:45 pm
EYW
- PWM
2 stops9h 53m
American Airlines
Deal found 5/5![American Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 5/3. 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.
Mon 6/296:00 am
PWM
- EYW
1 stop6h 23m
Delta
Fri 7/32:38 pm
EYW
- PWM
1 stop8h 27m
Delta
Deal found 5/3![Delta logo]()
$368
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/610:42 am
PWM
- EYW
1 stop8h 07m
American Airlines
Wed 6/104:44 pm
EYW
- PWM
1 stop6h 02m
American Airlines
Deal found 5/4![American Airlines logo]()
$374
Best flights from Portland to Key WestDiscover carefully curated flight deals from Portland to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 6, 2026.
Discover carefully curated flight deals from Portland to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 6, 2026.
This Delta deal was found by Cheapflights users on 5/3. 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 6/306:00 am
PWM
- EYW
1 stop7h 43m
Delta
Fri 7/32:38 pm
EYW
- PWM
1 stop8h 27m
Delta
Deal found 5/3![Delta logo]()
$355
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/77:58 am
PWM
- EYW
2 stops11h 12m
American Airlines
Sun 6/1411:28 am
EYW
- PWM
2 stops10h 18m
American Airlines
Deal found 5/1![American Airlines logo]()
$432
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/75:15 am
PWM
- EYW
2 stops9h 54m
United Airlines
Fri 6/122:26 pm
EYW
- PWM
2 stops9h 25m
United Airlines
Deal found 5/4![United Airlines logo]()
$511
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.
Sat 6/68:05 am
PWM
- EYW
2 stops11h 44m
Delta
Wed 6/102:28 pm
EYW
- PWM
1 stop8h 37m
Delta
Deal found 5/4![Delta logo]()
$360
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.
Sat 5/162:05 pm
PWM
- EYW
1 stop5h 44m
Delta
Wed 5/2011:48 am
EYW
- PWM
2 stops12h 55m
Delta
Deal found 5/4![Delta logo]()
$379
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:00 am
PWM
- EYW
2 stops10h 30m
American Airlines
Thu 5/216:45 am
EYW
- PWM
2 stops10h 22m
American Airlines
Deal found 5/1![American Airlines logo]()
$497
This United Airlines deal was found by Cheapflights users on 5/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/246:00 am
PWM
- EYW
1 stop9h 07m
United Airlines
Thu 5/282:26 pm
EYW
- PWM
2 stops9h 25m
United Airlines
Deal found 5/1![United Airlines logo]()
$658
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:00 am
PWM
- EYW
1 stop5h 29m
American Airlines
Sat 5/237:49 pm
EYW
- PWM
2 stops13h 49m
American Airlines
Deal found 5/6![American Airlines logo]()
$650
This Delta deal was found by Cheapflights users on 5/3. 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 5/162:05 pm
PWM
- EYW
1 stop5h 44m
Delta
Sat 5/237:30 am
EYW
- PWM
1 stop5h 40m
Delta
Deal found 5/3![Delta logo]()
$633
Last-minute flights from Portland to Key WestDiscover last-minute flight deals from Portland to Key West. Data last updated May 6, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Key West. Data last updated May 6, 2026 and is based on user searches.
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.
Sat 5/162:05 pm
PWM
- EYW
1 stop5h 44m
Delta
Wed 5/2011:48 am
EYW
- PWM
2 stops12h 55m
Delta
Deal found 5/4![Delta logo]()
$379
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:00 am
PWM
- EYW
2 stops10h 13m
American Airlines
Wed 5/2011:24 am
EYW
- PWM
2 stops12h 02m
American Airlines
Deal found 5/4![American Airlines logo]()
$385
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/18:04 am
PWM
- EYW
1 stop5h 37m
American Airlines
Sat 6/65:07 pm
EYW
- PWM
1 stop5h 22m
American Airlines
Deal found 5/1![American Airlines logo]()
$357
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.
Sat 6/66:26 pm
PWM
- EYW
1 stop15h 58m
Breeze Airways
Thu 6/1112:05 pm
EYW
- PWM
1 stop21h 07m
Breeze Airways
Deal found 5/5![Breeze Airways logo]()
$326
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.
Sat 6/68:05 am
PWM
- EYW
2 stops11h 44m
Delta
Wed 6/102:28 pm
EYW
- PWM
1 stop8h 37m
Delta
Deal found 5/4![Delta logo]()
$360
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/610:42 am
PWM
- EYW
1 stop8h 07m
American Airlines
Wed 6/104:44 pm
EYW
- PWM
1 stop6h 02m
American Airlines
Deal found 5/4![American Airlines logo]()
$374
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.
Sun 6/73:11 pm
PWM
- EYW
1 stop27h 16m
Multiple Airlines
Fri 6/1212:07 pm
EYW
- PWM
1 stop21h 05m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$330
This Delta deal was found by Cheapflights users on 5/3. 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.
Mon 6/296:00 am
PWM
- EYW
1 stop6h 23m
Delta
Fri 7/32:38 pm
EYW
- PWM
1 stop8h 27m
Delta
Deal found 5/3![Delta logo]()
$368
This Delta deal was found by Cheapflights users on 5/3. 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 6/306:00 am
PWM
- EYW
1 stop7h 43m
Delta
Fri 7/32:38 pm
EYW
- PWM
1 stop8h 27m
Delta
Deal found 5/3![Delta logo]()
$355
One-way flights from Portland to Key WestSearch for one-way flight options from Portland to Key West. Find affordable one-way fares based on user searches. Data last updated May 6, 2026.
Search for one-way flight options from Portland to Key West. Find affordable one-way fares based on user searches. Data last updated May 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Fri 5/226:13 pm
PWM
- EYW
2 stops40h 11m
Breeze Airways
Deal found 5/3![Breeze Airways logo]()
$212
This Delta deal was found by Cheapflights users on 5/3. 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.
Fri 5/222:05 pm
PWM
- EYW
1 stop5h 44m
Delta
Deal found 5/3![Delta logo]()
$290
Find flight deals from Portland to Key West
Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) 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 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $326 (Kiwi.com) |
One-way from | $212 (Kiwi.com) |
Popular in | February |
Cheapest in | June |
Average price | $372 |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland 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 6, 2026.
Use the filters below to find and compare flights from Portland to Key West that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandKey West
PWM - EYW
PWMEYW
Portland
Tue 6/30
6:00 am-1:43 pm
1 stop7h 43m
Key West
Fri 7/3
2:38 pm-11:05 pm
1 stop8h 27m
$355
PortlandKey West
PWM - EYW
PWMEYW
Portland
Sat 6/6
8:05 am-7:49 pm
2 stops11h 44m
Key West
Wed 6/10
2:28 pm-11:05 pm
1 stop8h 37m
$360
PortlandKey West
PWM - EYW
PWMEYW
Portland
Sat 5/16
2:05 pm-7:49 pm
1 stop5h 44m
Key West
Wed 5/20
11:48 am-12:43 am
2 stops12h 55m
$379
PortlandKey West
PWM - EYW
PWMEYW
Portland
Sun 6/7
7:58 am-7:10 pm
2 stops11h 12m
Key West
Sun 6/14
11:28 am-9:46 pm
2 stops10h 18m
$432
PortlandKey West
PWM - EYW
PWMEYW
Portland
Sun 5/17
6:00 am-4:30 pm
2 stops10h 30m
Key West
Thu 5/21
6:45 am-5:07 pm
2 stops10h 22m
$497
PortlandKey West
PWM - EYW
PWMEYW
Portland
Sun 6/7
5:15 am-3:09 pm
2 stops9h 54m
Key West
Fri 6/12
2:26 pm-11:51 pm
2 stops9h 25m
$511
Quickest round-trip
PortlandKey West
PWM - EYW
PWMEYW
Portland
Sat 5/16
2:05 pm-7:49 pm
1 stop5h 44m
Key West
Sat 5/23
7:30 am-1:10 pm
1 stop5h 40m
$633
PortlandKey West
PWM - EYW
PWMEYW
Portland
Sat 5/16
6:00 am-11:29 am
1 stop5h 29m
Key West
Sat 5/23
7:49 pm-9:38 am
2 stops13h 49m
$650
PortlandKey West
PWM - EYW
PWMEYW
Portland
Sun 5/24
6:00 am-3:07 pm
1 stop9h 07m
Key West
Thu 5/28
2:26 pm-11:51 pm
2 stops9h 25m
$658
Cheapest one-way
PortlandKey West
PWM - EYW
PWMEYW
Portland
Fri 5/22
6:13 pm-10:24 am
2 stops40h 11m
$212
Showing 1-10 of 11 resultsSorted by cheapest first
Compare providers for flights from Portland 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 Portland 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 Portland, Maine-Key West flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland, Maine-Key West flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland, Maine-Key West flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Portland, Maine-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 Portland, Maine-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 Portland to Key West
Have a flexible travel schedule? Discover the best time to fly to Key West from Portland with our price prediction graph.
PWM-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 Portland to Key West
How far ahead should I book a flight from Portland, Maine to Key West?
To ensure you get the cheapest price possible for a flight from Portland, Maine to Key West, you should look to book at least 25 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Portland, Maine to Key West?
Currently, June is the cheapest month in which you can book a flight from Portland, Maine to Key West (average of $319). Flying from Portland, Maine to Key West in February is currently the most expensive (average of $572). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Portland, Maine 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 6, 2026.
Read through reviews of airlines operating flights from Portland to Key West, such as Delta,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.9
Crew
8.5
Entertainment
7.8
Overall
7.9
Boarding
8.1
Food
7.2
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Comfort
7.9
Crew
8.5
Entertainment
7.8
Overall
7.9
Boarding
8.1
Food
7.2
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Comfort
7.9
Crew
8.5
Entertainment
7.8
Overall
7.9
Boarding
8.1
Food
7.2
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Comfort
7.9
Crew
8.5
Entertainment
7.8
Overall
7.9
Boarding
8.1
Food
7.2
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Related info for your journey
Find useful and relevant information for your journey from Portland 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.
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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 Portland to Key West by cabin class
Find flights from Portland 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 May 6, 2026.
Portland and Key West flights
Browse other Portland and Key West flight options. Last updated on May 6, 2026.
Other flights from Portland
Browse through other flights departing from Portland. Flights are based on user searches made on Cheapflights and were last updated on May 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Portland to Key West
Discover the top 3 airlines that operate flights from Portland 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 May 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$256 | Average$447 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$437 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$268 | Average$449 | FlexibilityNo cancel fee | On-time71% |