$144+ Cheap flights from Midway (MDW) to San Jose, CA (SJC)
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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJC
Oct 14 — Oct 211
Round-trip
1 adult, Economy
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Find cheap flights from Midway to San Jose 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 San Jose
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Cheapest flights from Midway to San JoseExplore the most affordable flight options available from Midway to San Jose. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 14, 2026.
Explore the most affordable flight options available from Midway to San Jose. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 14, 2026.
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/208:40 pm -
Nonstop4h 40m
Tue 11/311:10 am -
Nonstop4h 05m
Deal found 9/14![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/208:40 pm -
Nonstop4h 40m
Wed 11/412:20 pm -
1 stop8h 05m
Deal found 9/14![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:25 am -
1 stop8h 05m
Wed 10/211:15 pm -
1 stop7h 00m
Deal found 9/14![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:40 pm -
Nonstop4h 40m
Mon 10/266:00 am -
Nonstop4h 00m
Deal found 9/13![Southwest logo]()
$308
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:50 pm -
Nonstop4h 40m
Tue 12/18:35 pm -
1 stop7h 05m
Deal found 9/14![Southwest logo]()
$318
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/68:40 pm -
Nonstop4h 40m
Mon 10/266:00 am -
Nonstop4h 00m
Deal found 9/13![Southwest logo]()
$320
Best flights from Midway to San JoseDiscover carefully curated flight deals from Midway to San Jose that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 14, 2026.
Discover carefully curated flight deals from Midway to San Jose that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 14, 2026.
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/43:50 pm -
Nonstop4h 40m
Sat 11/78:30 am -
Nonstop4h 05m
Deal found 9/14![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 9/11. 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.
Thu 11/512:27 pm -
1 stop7h 26m
Wed 11/114:19 pm -
2 stops14h 31m
Deal found 9/11![Delta logo]()
$443
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.
Wed 11/258:40 pm -
Nonstop4h 45m
Wed 12/211:10 am -
Nonstop4h 05m
Deal found 9/9![Southwest logo]()
$386
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 11/249:55 am -
Nonstop4h 40m
Wed 12/26:00 am -
Nonstop4h 10m
Deal found 9/9![Southwest logo]()
$386
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.
Fri 10/1612:49 pm -
1 stop8h 11m
Tue 10/206:20 am -
1 stop8h 27m
Deal found 9/9![Delta logo]()
$477
This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1110:10 am -
Nonstop4h 45m
Fri 11/1311:00 pm -
Nonstop4h 00m
Deal found 9/11![Southwest logo]()
$401
This Delta deal was found by Cheapflights users on 9/13. 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.
Tue 10/276:04 am -
1 stop7h 40m
Tue 11/36:20 am -
1 stop8h 27m
Deal found 9/13![Delta logo]()
$477
This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/292:55 pm -
1 stop6h 35m
Fri 10/3010:20 am -
2 stops8h 15m
Deal found 9/11![Southwest logo]()
$422
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 10/2311:55 am -
1 stop7h 10m
Sun 10/259:25 pm -
1 stop6h 15m
Deal found 9/9![Southwest logo]()
$443
This Southwest deal was found by Cheapflights users on 9/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/213:45 pm -
2 stops7h 55m
Fri 11/2711:00 pm -
Nonstop4h 00m
Deal found 9/12![Southwest logo]()
$472
Last-minute flights from Midway to San JoseDiscover last-minute flight deals from Midway to San Jose. Data last updated September 14, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Jose. Data last updated September 14, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/68:40 pm -
Nonstop4h 40m
Mon 10/266:00 am -
Nonstop4h 00m
Deal found 9/13![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:25 am -
1 stop8h 05m
Wed 10/211:15 pm -
1 stop7h 00m
Deal found 9/14![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/208:40 pm -
Nonstop4h 40m
Wed 11/46:00 am -
Nonstop4h 10m
Deal found 9/14![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:25 am -
1 stop6h 40m
Tue 11/36:00 am -
Nonstop4h 10m
Deal found 9/14![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:40 pm -
Nonstop4h 40m
Mon 10/266:00 am -
Nonstop4h 00m
Deal found 9/13![Southwest logo]()
$308
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/229:15 pm -
Nonstop4h 40m
Mon 10/2611:00 pm -
Nonstop4h 00m
Deal found 9/13![Southwest logo]()
$329
One-way flights from Midway to San JoseSearch for one-way flight options from Midway to San Jose. Find affordable one-way fares based on user searches. Data last updated September 14, 2026.
Search for one-way flight options from Midway to San Jose. Find affordable one-way fares based on user searches. Data last updated September 14, 2026.
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:50 pm -
Nonstop4h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$144
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:25 am -
1 stop6h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$153
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/68:40 pm -
Nonstop4h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Southwest logo]()
$156
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.
Wed 10/213:30 pm -
2 stops30h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$166
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.
Wed 9/3010:20 am -
Nonstop4h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Southwest logo]()
$168
This Delta deal was found by Cheapflights users on 9/10. 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 11/79:29 am -
2 stops12h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Delta logo]()
$173
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.
Wed 10/76:25 am -
2 stops39h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$174
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/292:30 pm -
1 stop6h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Southwest logo]()
$175
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.
Wed 9/306:25 am -
2 stops39h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 9/12. 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.
Wed 11/116:16 am -
2 stops39h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Frontier logo]()
$177
Find flight deals from Midway to San Jose
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San Jose (SJC). 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 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $287 (Southwest) |
One-way from | $144 (Southwest) |
Popular in | May |
Cheapest in | April |
Average price | $395 |
Good round-trip deal | $303 or less |
Good one-way deal | $184 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to San Jose 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 14, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San Jose that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Jose
MDW Chicago Midway - SJC San Jose
MDWSJC
Chicago Midway
Wed 10/14
6:25 am-11:20 am
1 stop6h 55m
San Jose
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$153
Quickest round-trip
ChicagoSan Jose
MDW Chicago Midway - SJC San Jose
MDWSJC
Chicago Midway
Wed 12/9
3:50 pm-6:30 pm
Nonstop4h 40m
San Jose
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$168
ChicagoSan Jose
MDW Chicago Midway - SJC San Jose
MDWSJC
Chicago Midway
Thu 10/8
9:15 pm-11:55 pm
Nonstop4h 40m
San Jose
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$168
ChicagoSan Jose
MDW Chicago Midway - SJC San Jose
MDWSJC
Chicago Midway
Fri 11/6
4:19 pm-5:15 pm
2 stops26h 56m
San Jose
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$173
ChicagoSan Jose
MDW Chicago Midway - SJC San Jose
MDWSJC
Chicago Midway
Tue 11/10
6:00 am-11:50 am
1 stop7h 50m
San Jose
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$178
ChicagoSan Jose
MDW Chicago Midway - SJC San Jose
MDWSJC
Chicago Midway
Wed 11/11
6:00 am-11:50 am
1 stop7h 50m
San Jose
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$178
ChicagoSan Jose
MDW Chicago Midway - SJC San Jose
MDWSJC
Chicago Midway
Tue 12/8
6:00 am-5:23 pm
2 stops13h 23m
San Jose
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$183
ChicagoSan Jose
MDW Chicago Midway - SJC San Jose
MDWSJC
Chicago Midway
Fri 10/2
10:48 am-10:06 pm
2 stops13h 18m
San Jose
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$210
ChicagoSan Jose
MDW Chicago Midway - SJC San Jose
MDWSJC
Chicago Midway
Fri 10/16
9:15 pm-11:55 pm
Nonstop4h 40m
San Jose
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$229
ChicagoSan Jose
MDW Chicago Midway - SJC San Jose
MDWSJC
Chicago Midway
Wed 11/4
3:50 pm-6:30 pm
Nonstop4h 40m
San Jose
Sat 11/7
8:30 am-2:35 pm
Nonstop4h 05m
$287
Showing 1-10 of 19 resultsSorted by cheapest first
Compare providers for flights from Midway to San Jose
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 San Jose in September.
| 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-San Jose, California 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-San Jose, California flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-San Jose, California flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-San Jose, California 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-San Jose, California 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 San Jose
Have a flexible travel schedule? Discover the best time to fly to San Jose from Midway with our price prediction graph.
MDW-SJC
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 Chicago Midway Airport to San Jose
What is the cheapest time of day to fly from MDW to SJC?
Find hourly flight availability from Midway to San Jose. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 14, 2026.
One of the essential ways to save on airfare from Chicago Midway Airport to San Jose, California is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 25% on airfare.
How much does it cost to fly round-trip from Chicago Midway Airport to San Jose, California?
Airfare is below average for this route at the moment.
Chicago Midway Airport to San Jose, California flights typically cost between $395 and $443 in October.The cheapest round-trip price found within the last 5 days was $287 on Southwest (Oct 20-Nov 3).
The best insider tips for Chicago Midway Airport to San Jose flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to San Jose trip
Our travel experts
Reviews of airlines servicing San Jose
Get insights into the airlines that provide service to San Jose. 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 San Jose. Reviews last updated September 14, 2026.
Get a feel of what it's like to fly with Southwest from Chicago Midway Airport to San Jose by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Midway to San Jose. 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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Alternative routes for Midway to San Jose
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Complete your trip
Complete your trip to San Jose by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Midway to San Jose, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and San Jose flights
Browse other Midway and San Jose flight options. Last updated on September 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 September 14, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to San Jose
Explore flights to San Jose departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 14, 2026.
Top airline flying from Midway to San Jose
Discover the top airline that operate flights from Midway to San Jose. 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 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$298 | Average$488 | FlexibilityNo cancel fee | On-time63% |