$138+ Cheap flights from Midway (MDW) to San José (SJO)
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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
Jul 26 — Aug 21
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Midway to San José 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 José
Cheapest
Best
Last-minute
One-way
Cheapest flights from Midway to San JoséExplore the most affordable flight options available from Midway to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 26, 2026.
Explore the most affordable flight options available from Midway to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 26, 2026.
This Southwest deal was found by Cheapflights users on 6/21. 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.
Sun 11/85:15 am
MDW
- SJO
1 stop7h 05m
Southwest
Fri 11/139:00 am
SJO
- MDW
2 stops11h 25m
Southwest
Deal found 6/21![Southwest logo]()
$473
This Southwest deal was found by Cheapflights users on 6/21. 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 8/2410:05 am
MDW
- SJO
2 stops9h 35m
Southwest
Sun 8/309:00 am
SJO
- MDW
1 stop11h 20m
Southwest
Deal found 6/21![Southwest logo]()
$487
This Southwest deal was found by Cheapflights users on 6/24. 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 11/125:15 am
MDW
- SJO
1 stop7h 05m
Southwest
Sun 11/152:10 pm
SJO
- MDW
2 stops10h 55m
Southwest
Deal found 6/24![Southwest logo]()
$489
This Southwest deal was found by Cheapflights users on 6/24. 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.
Sat 10/315:00 am
MDW
- SJO
1 stop8h 00m
Southwest
Wed 11/49:00 am
SJO
- MDW
2 stops12h 20m
Southwest
Deal found 6/24![Southwest logo]()
$491
This Delta deal was found by Cheapflights users on 6/24. 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 10/56:05 am
MDW
- SJO
1 stop6h 49m
Delta
Wed 10/211:23 pm
SJO
- MDW
1 stop7h 47m
Delta
Deal found 6/24![Delta logo]()
$502
This Southwest deal was found by Cheapflights users on 6/23. 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 10/226:45 am
MDW
- SJO
1 stop6h 50m
Southwest
Mon 10/261:30 pm
SJO
- MDW
1 stop9h 40m
Southwest
Deal found 6/23![Southwest logo]()
$504
This Delta deal was found by Cheapflights users on 6/24. 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.
Sun 10/41:19 pm
MDW
- SJO
2 stops23h 35m
Delta
Wed 10/211:23 pm
SJO
- MDW
1 stop7h 47m
Delta
Deal found 6/24![Delta logo]()
$507
This Southwest deal was found by Cheapflights users on 6/21. 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.
Sun 9/277:10 am
MDW
- SJO
2 stops12h 30m
Southwest
Sat 10/39:00 am
SJO
- MDW
2 stops21h 25m
Southwest
Deal found 6/21![Southwest logo]()
$511
This Southwest deal was found by Cheapflights users on 6/24. 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.
Sun 11/158:40 pm
MDW
- SJO
2 stops15h 40m
Southwest
Thu 11/199:00 am
SJO
- MDW
2 stops12h 20m
Southwest
Deal found 6/24![Southwest logo]()
$513
This Southwest deal was found by Cheapflights users on 6/25. 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 9/277:10 am
MDW
- SJO
2 stops12h 30m
Southwest
Wed 9/309:00 am
SJO
- MDW
2 stops12h 20m
Southwest
Deal found 6/25![Southwest logo]()
$516
This Southwest deal was found by Cheapflights users on 6/25. 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 10/126:45 am
MDW
- SJO
1 stop6h 50m
Southwest
Sun 10/181:05 pm
SJO
- MDW
1 stop10h 50m
Southwest
Deal found 6/25![Southwest logo]()
$527
Best flights from Midway to San JoséDiscover carefully curated flight deals from Midway to San José that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 26, 2026.
Discover carefully curated flight deals from Midway to San José that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 26, 2026.
This Southwest deal was found by Cheapflights users on 6/21. 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.
Sat 7/48:55 am
MDW
- SJO
1 stop11h 20m
Southwest
Sat 7/112:35 pm
SJO
- MDW
1 stop7h 40m
Southwest
Deal found 6/21![Southwest logo]()
$588
This Delta deal was found by Cheapflights users on 6/22. 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.
Mon 8/316:05 am
MDW
- SJO
1 stop6h 44m
Delta
Mon 9/71:14 pm
SJO
- MDW
1 stop8h 22m
Delta
Deal found 6/22![Delta logo]()
$611
This Delta deal was found by Cheapflights users on 6/22. 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 9/226:05 am
MDW
- SJO
1 stop6h 49m
Delta
Wed 10/71:23 pm
SJO
- MDW
1 stop7h 47m
Delta
Deal found 6/22![Delta logo]()
$720
This Southwest deal was found by Cheapflights users on 6/25. 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 7/48:55 am
MDW
- SJO
1 stop11h 20m
Southwest
Fri 7/241:40 pm
SJO
- MDW
1 stop8h 25m
Southwest
Deal found 6/25![Southwest logo]()
$734
This Southwest deal was found by Cheapflights users on 6/21. 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 7/78:40 am
MDW
- SJO
2 stops12h 00m
Southwest
Sat 7/1112:15 pm
SJO
- MDW
2 stops10h 00m
Southwest
Deal found 6/21![Southwest logo]()
$835
This Delta deal was found by Cheapflights users on 6/26. 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 8/196:05 am
MDW
- SJO
1 stop6h 44m
Delta
Sun 8/231:14 pm
SJO
- MDW
1 stop8h 22m
Delta
Deal found 6/26![Delta logo]()
$903
This Southwest deal was found by Cheapflights users on 6/24. 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 7/318:55 am
MDW
- SJO
2 stops11h 45m
Southwest
Mon 8/31:40 pm
SJO
- MDW
2 stops10h 25m
Southwest
Deal found 6/24![Southwest logo]()
$836
This Southwest deal was found by Cheapflights users on 6/23. 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 7/2311:50 am
MDW
- SJO
1 stop8h 50m
Southwest
Thu 7/308:45 am
SJO
- MDW
1 stop10h 25m
Southwest
Deal found 6/23![Southwest logo]()
$876
This Southwest deal was found by Cheapflights users on 6/23. 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 7/1210:40 am
MDW
- SJO
1 stop9h 00m
Southwest
Thu 7/168:45 am
SJO
- MDW
1 stop10h 25m
Southwest
Deal found 6/23![Southwest logo]()
$891
This Southwest deal was found by Cheapflights users on 6/24. 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 7/1711:50 am
MDW
- SJO
1 stop8h 50m
Southwest
Mon 7/201:40 pm
SJO
- MDW
1 stop8h 25m
Southwest
Deal found 6/24![Southwest logo]()
$922
Last-minute flights from Midway to San JoséDiscover last-minute flight deals from Midway to San José. Data last updated June 26, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San José. Data last updated June 26, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/21. 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.
Thu 6/257:50 am
MDW
- SJO
2 stops12h 50m
Southwest
Sat 6/272:35 pm
SJO
- MDW
1 stop7h 35m
Southwest
Deal found 6/21![Southwest logo]()
$655
This Southwest deal was found by Cheapflights users on 6/24. 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 6/2510:10 am
MDW
- SJO
1 stop10h 30m
Southwest
Thu 7/28:45 am
SJO
- MDW
1 stop8h 15m
Southwest
Deal found 6/24![Southwest logo]()
$672
This Southwest deal was found by Cheapflights users on 6/25. 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 6/2610:10 am
MDW
- SJO
1 stop10h 30m
Southwest
Sat 7/2512:15 pm
SJO
- MDW
1 stop10h 00m
Southwest
Deal found 6/25![Southwest logo]()
$681
This Southwest deal was found by Cheapflights users on 6/25. 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 6/285:05 am
MDW
- SJO
1 stop7h 30m
Southwest
Sat 7/48:45 am
SJO
- MDW
1 stop10h 05m
Southwest
Deal found 6/25![Southwest logo]()
$677
This Southwest deal was found by Cheapflights users on 6/22. 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 7/47:45 am
MDW
- SJO
2 stops12h 30m
Southwest
Sat 7/112:35 pm
SJO
- MDW
1 stop7h 40m
Southwest
Deal found 6/22![Southwest logo]()
$588
This Frontier deal was found by Cheapflights users on 6/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/84:45 pm
MDW
- SJO
2 stops16h 35m
Frontier
Thu 8/139:35 am
SJO
- MDW
2 stops11h 28m
Frontier
Deal found 6/24![Frontier logo]()
$667
This Southwest deal was found by Cheapflights users on 6/24. 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.
Sat 7/115:05 am
MDW
- SJO
1 stop6h 55m
Southwest
Sat 7/188:45 am
SJO
- MDW
1 stop14h 00m
Southwest
Deal found 6/24![Southwest logo]()
$617
This Frontier deal was found by Cheapflights users on 6/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/224:45 pm
MDW
- SJO
2 stops16h 35m
Frontier
Sun 7/269:35 am
SJO
- MDW
2 stops11h 28m
Frontier
Deal found 6/24![Frontier logo]()
$682
One-way flights from Midway to San JoséSearch for one-way flight options from Midway to San José. Find affordable one-way fares based on user searches. Data last updated June 26, 2026.
Search for one-way flight options from Midway to San José. Find affordable one-way fares based on user searches. Data last updated June 26, 2026.
This Southwest deal was found by Cheapflights users on 6/24. 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.
Mon 9/75:00 am
MDW
- SJO
1 stop8h 45m
Southwest
Deal found 6/24![Southwest logo]()
$138
This Southwest deal was found by Cheapflights users on 6/22. 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 9/126:45 am
MDW
- SJO
2 stops12h 15m
Southwest
Deal found 6/22![Southwest logo]()
$195
This Southwest deal was found by Cheapflights users on 6/25. 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 9/86:15 am
MDW
- SJO
1 stop7h 30m
Southwest
Deal found 6/25![Southwest logo]()
$200
This Southwest deal was found by Cheapflights users on 6/24. 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.
Tue 9/159:00 am
MDW
- SJO
2 stops10h 40m
Southwest
Deal found 6/24![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 6/23. 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.
Fri 8/710:05 am
MDW
- SJO
1 stop9h 35m
Southwest
Deal found 6/23![Southwest logo]()
$230
This Southwest deal was found by Cheapflights users on 6/23. 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.
Wed 7/2912:00 pm
MDW
- SJO
1 stop8h 40m
Southwest
Deal found 6/23![Southwest logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 6/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1512:03 pm
MDW
- SJO
3 stops23h 35m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$245
This Southwest deal was found by Cheapflights users on 6/25. 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 8/310:10 am
MDW
- SJO
1 stop10h 30m
Southwest
Deal found 6/25![Southwest logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 6/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/811:06 am
MDW
- SJO
2 stops22h 14m
Frontier
Deal found 6/24![Frontier logo]()
$288
This Southwest deal was found by Cheapflights users on 6/23. 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.
Tue 7/288:40 am
MDW
- SJO
2 stops12h 00m
Southwest
Deal found 6/23![Southwest logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 6/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/294:45 pm
MDW
- SJO
3 stops57h 30m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$305
Find flight deals from Midway to San José
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San José (SJO). 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 June 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $473 (Southwest) |
One-way from | $138 (Southwest) |
Popular in | December |
Cheapest in | September |
Average price | $584 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to San José 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 June 26, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San José that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sat 7/4
8:55 am-7:15 pm
1 stop11h 20m
San José Juan Santamaria Intl
Sat 7/11
2:35 pm-11:15 pm
1 stop7h 40m
$588
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Mon 8/31
6:05 am-11:49 am
1 stop6h 44m
San José Juan Santamaria Intl
Mon 9/7
1:14 pm-10:36 pm
1 stop8h 22m
$611
Quickest round-trip
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Tue 9/22
6:05 am-11:54 am
1 stop6h 49m
San José Juan Santamaria Intl
Wed 10/7
1:23 pm-10:10 pm
1 stop7h 47m
$720
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sat 7/4
8:55 am-7:15 pm
1 stop11h 20m
San José Juan Santamaria Intl
Fri 7/24
1:40 pm-11:05 pm
1 stop8h 25m
$734
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Tue 7/7
8:40 am-7:40 pm
2 stops12h 00m
San José Juan Santamaria Intl
Sat 7/11
12:15 pm-11:15 pm
2 stops10h 00m
$835
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Fri 7/31
8:55 am-7:40 pm
2 stops11h 45m
San José Juan Santamaria Intl
Mon 8/3
1:40 pm-1:05 am
2 stops10h 25m
$836
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Thu 7/23
11:50 am-7:40 pm
1 stop8h 50m
San José Juan Santamaria Intl
Thu 7/30
8:45 am-8:10 pm
1 stop10h 25m
$876
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sun 7/12
10:40 am-6:40 pm
1 stop9h 00m
San José Juan Santamaria Intl
Thu 7/16
8:45 am-8:10 pm
1 stop10h 25m
$891
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Wed 8/19
6:05 am-11:49 am
1 stop6h 44m
San José Juan Santamaria Intl
Sun 8/23
1:14 pm-10:36 pm
1 stop8h 22m
$903
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Fri 7/17
11:50 am-7:40 pm
1 stop8h 50m
San José Juan Santamaria Intl
Mon 7/20
1:40 pm-11:05 pm
1 stop8h 25m
$922
Showing 1-10 of 19 resultsSorted by cheapest first
Compare providers for flights from Midway to San José
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 José in June.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-San José 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 José flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-San José flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-San José 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 José 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 José
Have a flexible travel schedule? Discover the best time to fly to San José from Midway with our price prediction graph.
MDW-SJO
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Reviews of airlines servicing San José
Get insights into the airlines that provide service to San José. 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 José. Reviews last updated June 26, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to San José, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Related info for your journey
Find useful and relevant information for your journey from Midway to San José. 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 San José?
Book flights to San José if you plan to visit one of these locationsAlajuela
Jacó
Heredia
Dominical
Manuel Antonio
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.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Midway
Popular flights
San José flight routes
Alternative routes for Midway to San José
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to San José by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to San José by cabin class
Find flights from Midway to San José, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and San José flights
Browse other Midway and San José flight options. Last updated on June 26, 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 June 26, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to San José
Explore flights to San José departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 26, 2026.
Top airline flying from Midway to San José
Discover the top airline that operate flights from Midway to San José. 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 June 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$394 | Average$547 | FlexibilityNo cancel fee | On-time63% |