$198+ Cheap flights from San José (SJO) to Midway (MDW)
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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Aug 24 — Aug 311
Round-trip
1 adult, Economy
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Find cheap flights from San José to Midway 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 San José to Midway
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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 July 25, 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 July 25, 2026.
This Southwest deal was found by Cheapflights users on 7/20. 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 9/171:40 pm
SJO
- MDW
1 stop7h 35m
Southwest
Wed 9/2310:30 am
MDW
- SJO
1 stop9h 10m
Southwest
Deal found 7/20![Southwest logo]()
$399
This Southwest deal was found by Cheapflights users on 7/20. 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 9/191:15 pm
SJO
- MDW
1 stop7h 45m
Southwest
Sat 9/269:55 am
MDW
- SJO
2 stops9h 05m
Southwest
Deal found 7/20![Southwest logo]()
$401
This Southwest deal was found by Cheapflights users on 7/20. 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 9/261:15 pm
SJO
- MDW
1 stop7h 45m
Southwest
Sat 10/311:25 am
MDW
- SJO
2 stops9h 15m
Southwest
Deal found 7/20![Southwest logo]()
$403
This Southwest deal was found by Cheapflights users on 7/21. 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 9/299:00 am
SJO
- MDW
1 stop9h 15m
Southwest
Tue 10/69:40 am
MDW
- SJO
2 stops11h 00m
Southwest
Deal found 7/21![Southwest logo]()
$405
This Southwest deal was found by Cheapflights users on 7/23. 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 9/211:40 pm
SJO
- MDW
1 stop7h 40m
Southwest
Mon 9/285:00 am
MDW
- SJO
1 stop8h 45m
Southwest
Deal found 7/23![Southwest logo]()
$406
This Southwest deal was found by Cheapflights users on 7/23. 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 10/291:30 pm
SJO
- MDW
1 stop7h 50m
Southwest
Wed 11/45:15 am
MDW
- SJO
1 stop8h 00m
Southwest
Deal found 7/23![Southwest logo]()
$411
This Southwest deal was found by Cheapflights users on 7/24. 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 9/181:40 pm
SJO
- MDW
1 stop7h 40m
Southwest
Fri 9/2510:05 am
MDW
- SJO
2 stops9h 40m
Southwest
Deal found 7/24![Southwest logo]()
$414
This Southwest deal was found by Cheapflights users on 7/21. 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 11/22:10 pm
SJO
- MDW
1 stop10h 55m
Southwest
Sun 11/85:15 am
MDW
- SJO
1 stop7h 05m
Southwest
Deal found 7/21![Southwest logo]()
$420
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 July 25, 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 July 25, 2026.
This Southwest deal was found by Cheapflights users on 7/24. 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 12/32:15 pm
SJO
- MDW
1 stop8h 50m
Southwest
Mon 12/75:15 am
MDW
- SJO
1 stop8h 00m
Southwest
Deal found 7/24![Southwest logo]()
$469
This Delta deal was found by Cheapflights users on 7/21. 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 1/217:05 am
SJO
- MDW
1 stop15h 05m
Delta
Sun 1/249:30 am
MDW
- SJO
2 stops12h 35m
Delta
Deal found 7/21![Delta logo]()
$518
This Southwest deal was found by Cheapflights users on 7/24. 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 9/259:00 am
SJO
- MDW
2 stops9h 30m
Southwest
Fri 10/29:40 am
MDW
- SJO
2 stops11h 00m
Southwest
Deal found 7/24![Southwest logo]()
$470
This Delta deal was found by Cheapflights users on 7/22. 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 11/247:00 am
SJO
- MDW
2 stops11h 37m
Delta
Wed 12/21:00 pm
MDW
- SJO
2 stops9h 15m
Delta
Deal found 7/22![Delta logo]()
$518
This Southwest deal was found by Cheapflights users on 7/22. 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 11/213:50 pm
SJO
- MDW
1 stop8h 30m
Southwest
Sat 11/288:55 pm
MDW
- SJO
2 stops16h 20m
Southwest
Deal found 7/22![Southwest logo]()
$513
This Delta deal was found by Cheapflights users on 7/24. 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 11/192:30 pm
SJO
- MDW
1 stop7h 40m
Delta
Wed 11/251:00 pm
MDW
- SJO
2 stops9h 15m
Delta
Deal found 7/24![Delta logo]()
$608
This Delta deal was found by Cheapflights users on 7/24. 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 12/257:00 am
SJO
- MDW
1 stop15h 10m
Delta
Wed 12/309:30 am
MDW
- SJO
2 stops12h 45m
Delta
Deal found 7/24![Delta logo]()
$697
This Delta deal was found by Cheapflights users on 7/21. 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 11/147:00 am
SJO
- MDW
1 stop15h 10m
Delta
Sat 11/2810:35 am
MDW
- SJO
1 stop11h 40m
Delta
Deal found 7/21![Delta logo]()
$698
This Delta deal was found by Cheapflights users on 7/21. 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 1/217:05 am
SJO
- MDW
2 stops11h 32m
Delta
Thu 1/2810:35 am
MDW
- SJO
1 stop11h 30m
Delta
Deal found 7/21![Delta logo]()
$735
This Delta deal was found by Cheapflights users on 7/20. 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 9/211:19 pm
SJO
- MDW
1 stop8h 25m
Delta
Sat 9/266:05 am
MDW
- SJO
1 stop6h 49m
Delta
Deal found 7/20![Delta logo]()
$739
This Delta deal was found by Cheapflights users on 7/24. 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 1/187:05 am
SJO
- MDW
1 stop15h 05m
Delta
Sun 1/2410:35 am
MDW
- SJO
1 stop11h 30m
Delta
Deal found 7/24![Delta logo]()
$752
This Delta deal was found by Cheapflights users on 7/24. 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 8/211:14 pm
SJO
- MDW
1 stop8h 22m
Delta
Fri 8/286:05 am
MDW
- SJO
1 stop6h 44m
Delta
Deal found 7/24![Delta logo]()
$752
Last-minute flights from San José to MidwayDiscover last-minute flight deals from San José to Midway. Data last updated July 25, 2026 and is based on user searches.
Discover last-minute flight deals from San José to Midway. Data last updated July 25, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/21. 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 7/241:40 pm
SJO
- MDW
1 stop8h 25m
Southwest
Wed 7/2912:00 pm
MDW
- SJO
1 stop8h 40m
Southwest
Deal found 7/21![Southwest logo]()
$479
This Southwest deal was found by Cheapflights users on 7/24. 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 7/311:40 pm
SJO
- MDW
1 stop8h 25m
Southwest
Fri 8/710:05 am
MDW
- SJO
2 stops9h 35m
Southwest
Deal found 7/24![Southwest logo]()
$557
This Southwest deal was found by Cheapflights users on 7/23. 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 8/18:45 am
SJO
- MDW
1 stop12h 15m
Southwest
Mon 8/3110:05 am
MDW
- SJO
2 stops9h 35m
Southwest
Deal found 7/23![Southwest logo]()
$460
This Southwest deal was found by Cheapflights users on 7/23. 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 8/18:45 am
SJO
- MDW
1 stop14h 00m
Southwest
Mon 8/175:00 am
MDW
- SJO
1 stop8h 45m
Southwest
Deal found 7/23![Southwest logo]()
$574
This Faresmojo deal was found by Cheapflights users on 7/23. 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.
Sun 8/212:00 pm
SJO
- MDW
1 stop10h 45m
JetBlue
Mon 8/105:00 am
MDW
- SJO
1 stop8h 45m
JetBlue
Deal found 7/23![JetBlue logo]()
$535
This Faresmojo deal was found by Cheapflights users on 7/23. 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.
Sat 8/221:15 pm
SJO
- MDW
1 stop17h 50m
JetBlue
Sat 8/297:20 am
MDW
- SJO
1 stop11h 40m
JetBlue
Deal found 7/23![JetBlue logo]()
$499
This Southwest deal was found by Cheapflights users on 7/20. 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 8/279:00 am
SJO
- MDW
1 stop8h 00m
Southwest
Mon 8/315:00 am
MDW
- SJO
1 stop8h 45m
Southwest
Deal found 7/20![Southwest logo]()
$518
This Faresmojo deal was found by Cheapflights users on 7/23. 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.
Fri 8/289:00 am
SJO
- MDW
1 stop12h 40m
JetBlue
Sun 8/3010:40 am
MDW
- SJO
1 stop9h 00m
JetBlue
Deal found 7/23![JetBlue logo]()
$488
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 July 25, 2026.
Search for one-way flight options from San José to Midway. Find affordable one-way fares based on user searches. Data last updated July 25, 2026.
This Southwest deal was found by Cheapflights users on 7/21. 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 10/71:00 pm
SJO
- MDW
1 stop9h 10m
Southwest
Deal found 7/21![Southwest logo]()
$198
This Southwest deal was found by Cheapflights users on 7/22. 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 10/209:00 am
SJO
- MDW
1 stop8h 35m
Southwest
Deal found 7/22![Southwest logo]()
$251
This Southwest deal was found by Cheapflights users on 7/20. 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 10/229:00 am
SJO
- MDW
2 stops10h 10m
Southwest
Deal found 7/20![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 7/24. 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 10/301:30 pm
SJO
- MDW
1 stop7h 50m
Southwest
Deal found 7/24![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 7/23. 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 12/213:25 pm
SJO
- MDW
2 stops17h 15m
Southwest
Deal found 7/23![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 7/22. 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 10/159:00 am
SJO
- MDW
1 stop10h 20m
Southwest
Deal found 7/22![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 7/23. 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 12/203:25 pm
SJO
- MDW
1 stop7h 40m
Southwest
Deal found 7/23![Southwest logo]()
$293
This Southwest deal was found by Cheapflights users on 7/23. 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 10/199:00 am
SJO
- MDW
2 stops13h 05m
Southwest
Deal found 7/23![Southwest logo]()
$303
This Southwest deal was found by Cheapflights users on 7/20. 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 9/11:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Deal found 7/20![Southwest logo]()
$308
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 July 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $399 (Southwest) |
One-way from | $198 (Southwest) |
Popular in | July |
Cheapest in | November |
Average price | $881 |
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 2,558,603 searches. Data last updated July 25, 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 - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 12/3
2:15 pm-11:05 pm
1 stop8h 50m
Chicago Midway
Mon 12/7
5:15 am-1:15 pm
1 stop8h 00m
$469
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Fri 9/25
9:00 am-7:30 pm
2 stops9h 30m
Chicago Midway
Fri 10/2
9:40 am-7:40 pm
2 stops11h 00m
$470
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Sat 11/21
3:50 pm-12:20 am
1 stop8h 30m
Chicago Midway
Sat 11/28
8:55 pm-1:15 pm
2 stops16h 20m
$513
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 1/21
7:05 am-10:10 pm
1 stop15h 05m
Chicago Midway
Sun 1/24
9:30 am-10:05 pm
2 stops12h 35m
$518
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Tue 11/24
7:00 am-6:37 pm
2 stops11h 37m
Chicago Midway
Wed 12/2
1:00 pm-10:15 pm
2 stops9h 15m
$518
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 11/19
2:30 pm-10:10 pm
1 stop7h 40m
Chicago Midway
Wed 11/25
1:00 pm-10:15 pm
2 stops9h 15m
$608
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Fri 12/25
7:00 am-10:10 pm
1 stop15h 10m
Chicago Midway
Wed 12/30
9:30 am-10:15 pm
2 stops12h 45m
$697
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Sat 11/14
7:00 am-10:10 pm
1 stop15h 10m
Chicago Midway
Sat 11/28
10:35 am-10:15 pm
1 stop11h 40m
$698
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 1/21
7:05 am-6:37 pm
2 stops11h 32m
Chicago Midway
Thu 1/28
10:35 am-10:05 pm
1 stop11h 30m
$735
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Mon 9/21
1:19 pm-10:44 pm
1 stop8h 25m
Chicago Midway
Sat 9/26
6:05 am-11:54 am
1 stop6h 49m
$739
Showing 1-10 of 22 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, November is the cheapest month in which you can book a flight from San José to Chicago Midway Airport (average of $358). Flying from San José to Chicago Midway Airport in July is currently the most expensive (average of $881). 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 below average for this route at the moment.
San José to Chicago Midway Airport flights typically cost between $638 and $827 in September.The cheapest round-trip price found within the last 5 days was $399 on Southwest (Sep 17-Sep 23).
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 July 25, 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.
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
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
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on July 25, 2026.
San José and Midway flights
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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 2,558,603 searches. Data last updated July 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$390 | Average$555 | FlexibilityNo cancel fee | On-time63% |