$235+ Cheap flights from San José (SJO) to Midway (MDW)
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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Oct 10 — Oct 171
Round-trip
1 adult, Economy
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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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Cheapest flights from San José to MidwayExplore the most affordable flight options available from San José to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 10, 2026.
Explore the most affordable flight options available from San José to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 10, 2026.
This Delta deal was found by Cheapflights users on 9/5. 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 11/72:25 pm -
1 stop8h 08m
Wed 11/111:05 pm -
1 stop9h 10m
Deal found 9/5![Delta logo]()
$366
This Delta deal was found by Cheapflights users on 9/7. 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 10/241:25 pm -
1 stop8h 08m
Thu 10/296:04 am -
1 stop6h 56m
Deal found 9/7![Delta logo]()
$387
This Southwest deal was found by Cheapflights users on 9/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:30 pm -
1 stop7h 50m
Thu 10/2911:50 am -
1 stop8h 50m
Deal found 9/8![Southwest logo]()
$432
This Delta deal was found by Cheapflights users on 9/7. 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.
Thu 11/122:37 pm -
1 stop8h 17m
Tue 11/176:00 am -
1 stop7h 12m
Deal found 9/7![Delta logo]()
$437
This Southwest deal was found by Cheapflights users on 9/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/91:20 pm -
1 stop9h 35m
Sun 11/155:15 am -
1 stop7h 05m
Deal found 9/5![Southwest logo]()
$453
This Southwest deal was found by Cheapflights users on 9/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/219:00 am -
2 stops9h 40m
Wed 10/285:45 am -
1 stop7h 20m
Deal found 9/5![Southwest logo]()
$463
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:25 pm -
1 stop8h 08m
Wed 10/286:04 am -
1 stop6h 56m
Deal found 9/9![Delta logo]()
$465
This Faresmojo deal was found by Cheapflights users on 9/6. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/81:25 pm -
1 stop8h 08m
Tue 10/136:04 am -
1 stop6h 56m
Deal found 9/6![JetBlue logo]()
$475
This Southwest deal was found by Cheapflights users on 9/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/289:00 am -
2 stops9h 40m
Sun 11/15:15 am -
1 stop7h 05m
Deal found 9/7![Southwest logo]()
$481
Best flights from San José to MidwayDiscover carefully curated flight deals from San José to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 10, 2026.
Discover carefully curated flight deals from San José to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 10, 2026.
This Southwest deal was found by Cheapflights users on 9/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/91:20 pm -
1 stop9h 35m
Sun 11/155:15 am -
1 stop7h 05m
Deal found 9/5![Southwest logo]()
$453
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/132:10 pm -
1 stop8h 00m
Wed 1/201:00 pm -
2 stops9h 05m
Deal found 9/9![Delta logo]()
$549
This Southwest deal was found by Cheapflights users on 9/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/81:20 pm -
1 stop9h 35m
Sun 11/155:15 am -
1 stop7h 05m
Deal found 9/5![Southwest logo]()
$481
This Delta deal was found by Cheapflights users on 9/6. 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 2/107:05 am -
2 stops11h 32m
Tue 2/169:30 am -
2 stops12h 35m
Deal found 9/6![Delta logo]()
$549
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/181:50 pm -
2 stops18h 40m
Wed 2/245:25 am -
1 stop8h 20m
Deal found 9/9![Southwest logo]()
$540
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/201:25 pm -
1 stop8h 08m
Mon 10/266:04 am -
1 stop6h 56m
Deal found 9/7![Delta logo]()
$559
This Southwest deal was found by Cheapflights users on 9/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/139:00 am -
2 stops9h 40m
Mon 10/197:25 am -
2 stops13h 15m
Deal found 9/5![Southwest logo]()
$592
This Delta deal was found by Cheapflights users on 9/8. 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 2/107:05 am -
2 stops11h 32m
Wed 2/179:30 am -
2 stops12h 35m
Deal found 9/8![Delta logo]()
$623
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/171:00 pm -
1 stop8h 20m
Wed 10/2112:25 pm -
1 stop8h 15m
Deal found 9/9![Southwest logo]()
$673
This Delta deal was found by Cheapflights users on 9/8. 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 12/267:00 am -
1 stop15h 22m
Thu 1/79:30 am -
2 stops12h 35m
Deal found 9/8![Delta logo]()
$755
Last-minute flights from San José to MidwayDiscover last-minute flight deals from San José to Midway. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from San José to Midway. Data last updated September 10, 2026 and is based on user searches.
This Faresmojo deal was found by Cheapflights users on 9/6. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/81:25 pm -
1 stop8h 08m
Tue 10/136:04 am -
1 stop6h 56m
Deal found 9/6![JetBlue logo]()
$475
This Southwest deal was found by Cheapflights users on 9/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/219:00 am -
2 stops9h 40m
Wed 10/285:45 am -
1 stop7h 20m
Deal found 9/5![Southwest logo]()
$463
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:25 pm -
1 stop8h 08m
Wed 10/286:04 am -
1 stop6h 56m
Deal found 9/9![Delta logo]()
$465
This Southwest deal was found by Cheapflights users on 9/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:30 pm -
1 stop7h 50m
Thu 10/2911:50 am -
1 stop8h 50m
Deal found 9/8![Southwest logo]()
$432
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:30 pm -
1 stop7h 50m
Sun 11/15:15 am -
1 stop7h 05m
Deal found 9/9![Southwest logo]()
$488
This Delta deal was found by Cheapflights users on 9/7. 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 10/241:25 pm -
1 stop8h 08m
Thu 10/296:04 am -
1 stop6h 56m
Deal found 9/7![Delta logo]()
$387
This KAYAK deal was found by Cheapflights users on 9/7. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/269:00 am -
1 stop23h 50m
Wed 10/286:25 am -
1 stop14h 15m
Deal found 9/7![Southwest logo]()
$492
This Southwest deal was found by Cheapflights users on 9/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/289:00 am -
2 stops9h 40m
Sun 11/15:15 am -
1 stop7h 05m
Deal found 9/7![Southwest logo]()
$481
One-way flights from San José to MidwaySearch for one-way flight options from San José to Midway. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
Search for one-way flight options from San José to Midway. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
This Southwest deal was found by Cheapflights users on 9/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/31:20 pm -
1 stop7h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Southwest logo]()
$235
This Southwest deal was found by Cheapflights users on 9/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/62:10 pm -
1 stop10h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/243:25 pm -
1 stop7h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Southwest logo]()
$275
This KAYAK deal was found by Cheapflights users on 9/7. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/269:00 am -
1 stop22h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/222:45 pm -
1 stop8h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Southwest logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/79:55 am -
2 stops13h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$300
This Southwest deal was found by Cheapflights users on 9/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/61:00 pm -
1 stop9h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Southwest logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/78:55 am -
3 stops31h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$313
Find flight deals from San José to Midway
Discover tips and strategies to find the most affordable flight options for your journey from San José (SJO) to Midway (MDW). 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 September 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $366 (Delta) |
One-way from | $235 (Southwest) |
Popular in | July |
Cheapest in | January |
Average price | $411 |
Cheapflights Fare Finder
Customize your flight search to find flights from San José to Midway 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 September 10, 2026.
Use the filters below to find and compare flights from San José to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Thu 12/3
1:20 pm-9:15 pm
1 stop7h 55m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$235
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Mon 10/26
9:00 am-8:25 am
1 stop22h 25m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$281
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Fri 10/23
1:30 pm-10:20 pm
1 stop7h 50m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$305
Quickest round-trip
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Sat 11/7
2:40 pm-10:20 pm
1 stop7h 40m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$320
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Mon 10/5
1:30 pm-10:15 pm
1 stop7h 45m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$328
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Wed 10/7
8:55 am-5:45 pm
2 stops31h 50m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$339
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Thu 10/8
9:00 am-8:20 pm
1 stop10h 20m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$441
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Mon 11/9
1:20 pm-10:55 pm
1 stop9h 35m
Chicago Midway
Sun 11/15
5:15 am-12:20 pm
1 stop7h 05m
$453
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Sat 10/24
1:25 pm-10:33 pm
1 stop8h 08m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$474
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Tue 10/20
1:25 pm-10:33 pm
1 stop8h 08m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$474
Showing 1-10 of 20 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on San José-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San José-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San José-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San José-Chicago Midway Airport 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 San José-Chicago Midway Airport 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 San José to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from San José with our price prediction graph.
SJO-MDW
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 San José to Chicago Midway Airport
What is the cheapest month to book a flight from San José to Chicago Midway Airport?
Currently, January is the cheapest month in which you can book a flight from San José to Chicago Midway Airport (average of $385). Flying from San José to Chicago Midway Airport in July is currently the most expensive (average of $902). 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 San José to Chicago Midway Airport?
Airfare is typical for this route at the moment.
San José to Chicago Midway Airport flights typically cost between $366 and $594 in November.The cheapest round-trip price found within the last 5 days was $366 on Delta (Nov 7-Nov 11).
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated September 10, 2026.
Read through reviews of airlines operating flights from San José to Chicago Midway Airport, such as Southwest. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from San José to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 10, 2026.
San José and Midway flights
Browse other San José and Midway flight options. Last updated on September 10, 2026.
Other flights from San José
Browse through other flights departing from San José. Flights are based on user searches made on Cheapflights and were last updated on September 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from San José to Midway
Discover the top airline that operate flights from San José to Midway. 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 September 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$390 | Average$589 | FlexibilityNo cancel fee | On-time63% |