$169+ 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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
Jun 9 — Jun 161
Round-trip
1 adult, Economy
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Find cheap flights from Midway to San José with Cheapflights
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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 May 10, 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 May 10, 2026.
This Frontier deal was found by Cheapflights users on 5/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/243:22 pm
MDW
- SJO
2 stops17h 58m
Frontier
Mon 8/249:35 am
SJO
- MDW
2 stops11h 36m
Frontier
Deal found 5/7![Frontier logo]()
$459
This Frontier deal was found by Cheapflights users on 5/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/243:22 pm
MDW
- SJO
2 stops17h 58m
Frontier
Sat 8/299:35 am
SJO
- MDW
2 stops11h 36m
Frontier
Deal found 5/7![Frontier logo]()
$465
This Delta deal was found by Cheapflights users on 5/7. 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 11/266:00 am
MDW
- SJO
1 stop16h 15m
Delta
Mon 12/77:00 am
SJO
- MDW
1 stop14h 45m
Delta
Deal found 5/7![Delta logo]()
$482
This Frontier deal was found by Cheapflights users on 5/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/73:22 pm
MDW
- SJO
2 stops17h 58m
Frontier
Sat 8/159:35 am
SJO
- MDW
2 stops11h 33m
Frontier
Deal found 5/9![Frontier logo]()
$485
This Delta deal was found by Cheapflights users on 5/7. 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 11/261:00 pm
MDW
- SJO
2 stops9h 15m
Delta
Wed 12/27:00 am
SJO
- MDW
2 stops11h 37m
Delta
Deal found 5/7![Delta logo]()
$487
This Frontier deal was found by Cheapflights users on 5/8. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/203:02 pm
MDW
- SJO
2 stops18h 18m
Frontier
Mon 8/249:35 am
SJO
- MDW
2 stops11h 36m
Frontier
Deal found 5/8![Frontier logo]()
$499
This Frontier deal was found by Cheapflights users on 5/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/213:02 pm
MDW
- SJO
2 stops18h 18m
Frontier
Sun 8/309:35 am
SJO
- MDW
2 stops11h 36m
Frontier
Deal found 5/9![Frontier logo]()
$513
This Southwest deal was found by Cheapflights users on 5/7. 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.
Thu 9/310:05 am
MDW
- SJO
1 stop9h 35m
Southwest
Tue 9/151:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Deal found 5/7![Southwest logo]()
$514
This Delta deal was found by Cheapflights users on 5/7. 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 11/281:05 pm
MDW
- SJO
1 stop9h 10m
Delta
Mon 12/77:00 am
SJO
- MDW
1 stop14h 45m
Delta
Deal found 5/7![Delta logo]()
$524
This Delta deal was found by Cheapflights users on 5/9. 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.
Sat 10/176:45 pm
MDW
- SJO
2 stops18h 13m
Delta
Sat 10/241:23 pm
SJO
- MDW
2 stops18h 22m
Delta
Deal found 5/9![Delta logo]()
$529
This Frontier deal was found by Cheapflights users on 5/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/243:22 pm
MDW
- SJO
2 stops17h 58m
Frontier
Fri 8/219:35 am
SJO
- MDW
2 stops11h 36m
Frontier
Deal found 5/9![Frontier logo]()
$533
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 May 10, 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 May 10, 2026.
This Delta deal was found by Cheapflights users on 5/10. 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 9/196:00 am
MDW
- SJO
1 stop6h 54m
Delta
Sat 9/261:25 pm
SJO
- MDW
1 stop7h 21m
Delta
Deal found 5/10![Delta logo]()
$566
This Southwest deal was found by Cheapflights users on 5/7. 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.
Sat 8/2210:25 am
MDW
- SJO
1 stop8h 35m
Southwest
Sun 9/69:00 am
SJO
- MDW
1 stop11h 50m
Southwest
Deal found 5/7![Southwest logo]()
$567
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/255:05 am
MDW
- SJO
1 stop6h 55m
Southwest
Wed 8/121:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Deal found 5/5![Southwest logo]()
$581
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:15 am
MDW
- SJO
1 stop7h 05m
Southwest
Tue 11/109:00 am
SJO
- MDW
2 stops12h 30m
Southwest
Deal found 5/5![Southwest logo]()
$586
This Southwest deal was found by Cheapflights users on 5/9. 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 8/1310:05 am
MDW
- SJO
2 stops9h 35m
Southwest
Sun 8/239:00 am
SJO
- MDW
1 stop11h 20m
Southwest
Deal found 5/9![Southwest logo]()
$587
This Delta deal was found by Cheapflights users on 5/9. 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 7/246:00 am
MDW
- SJO
1 stop6h 51m
Delta
Thu 8/201:14 pm
SJO
- MDW
1 stop8h 22m
Delta
Deal found 5/9![Delta logo]()
$720
This Delta deal was found by Cheapflights users on 5/7. 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 6/96:00 am
MDW
- SJO
1 stop6h 54m
Delta
Tue 6/161:19 pm
SJO
- MDW
1 stop7h 58m
Delta
Deal found 5/7![Delta logo]()
$720
This Delta deal was found by Cheapflights users on 5/9. 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.
Sat 7/256:00 am
MDW
- SJO
1 stop6h 51m
Delta
Mon 8/171:14 pm
SJO
- MDW
2 stops19h 03m
Delta
Deal found 5/9![Delta logo]()
$725
This Southwest deal was found by Cheapflights users on 5/7. 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.
Thu 5/2810:15 am
MDW
- SJO
1 stop9h 45m
Southwest
Mon 6/19:00 am
SJO
- MDW
2 stops10h 15m
Southwest
Deal found 5/7![Southwest logo]()
$721
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:50 am
MDW
- SJO
2 stops12h 10m
Southwest
Sat 5/309:00 am
SJO
- MDW
1 stop10h 25m
Southwest
Deal found 5/6![Southwest logo]()
$735
Last-minute flights from Midway to San JoséDiscover last-minute flight deals from Midway to San José. Data last updated May 10, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San José. Data last updated May 10, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/8. 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 5/96:23 am
MDW
- SJO
1 stop7h 52m
Delta
Sat 5/162:40 pm
SJO
- MDW
2 stops17h 03m
Delta
Deal found 5/8![Delta logo]()
$573
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1010:50 am
MDW
- SJO
2 stops9h 10m
Southwest
Tue 5/121:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Deal found 5/6![Southwest logo]()
$570
This Southwest deal was found by Cheapflights users on 5/7. 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.
Fri 5/155:35 am
MDW
- SJO
1 stop7h 35m
Southwest
Thu 5/219:00 am
SJO
- MDW
2 stops10h 15m
Southwest
Deal found 5/7![Southwest logo]()
$592
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/184:52 pm
MDW
- SJO
1 stop23h 26m
Multiple Airlines
Wed 5/277:00 am
SJO
- MDW
2 stops38h 02m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$576
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/184:52 pm
MDW
- SJO
1 stop23h 26m
Multiple Airlines
Thu 5/219:35 am
SJO
- MDW
2 stops11h 27m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$642
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:50 am
MDW
- SJO
2 stops12h 10m
Southwest
Wed 5/279:00 am
SJO
- MDW
2 stops12h 15m
Southwest
Deal found 5/5![Southwest logo]()
$636
This Southwest deal was found by Cheapflights users on 5/7. 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 5/266:00 am
MDW
- SJO
1 stop7h 10m
Southwest
Sat 6/68:45 am
SJO
- MDW
1 stop12h 10m
Southwest
Deal found 5/7![Southwest logo]()
$630
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Wed 6/101:40 pm
SJO
- MDW
1 stop9h 10m
Southwest
Deal found 5/6![Southwest logo]()
$617
This Southwest deal was found by Cheapflights users on 5/8. 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 6/410:10 am
MDW
- SJO
1 stop10h 30m
Southwest
Wed 6/101:40 pm
SJO
- MDW
1 stop9h 10m
Southwest
Deal found 5/8![Southwest logo]()
$549
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 May 10, 2026.
Search for one-way flight options from Midway to San José. Find affordable one-way fares based on user searches. Data last updated May 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:00 am
MDW
- SJO
2 stops27h 20m
Frontier
Deal found 5/7![Frontier logo]()
$169
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:00 am
MDW
- SJO
1 stop6h 56m
Delta
Deal found 5/5![Delta logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/512:11 pm
MDW
- SJO
2 stops21h 09m
Frontier
Deal found 5/5![Frontier logo]()
$206
This Southwest deal was found by Cheapflights users on 5/7. 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 9/166:15 am
MDW
- SJO
1 stop7h 30m
Southwest
Deal found 5/7![Southwest logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/812:11 pm
MDW
- SJO
2 stops21h 09m
Frontier
Deal found 5/10![Frontier logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2812:11 pm
MDW
- SJO
2 stops28h 00m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$231
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3011:35 am
MDW
- SJO
1 stop9h 05m
Southwest
Deal found 5/6![Southwest logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/112:11 pm
MDW
- SJO
2 stops21h 09m
Frontier
Deal found 5/10![Frontier logo]()
$256
This eDestinos deal was found by Cheapflights users on 5/10. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/176:00 am
MDW
- SJO
2 stops27h 20m
Frontier
Deal found 5/10![Frontier logo]()
$257
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:05 am
MDW
- SJO
1 stop6h 44m
Delta
Deal found 5/5![Delta logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2512:11 pm
MDW
- SJO
2 stops21h 09m
Frontier
Deal found 5/6![Frontier logo]()
$274
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 May 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $459 (Frontier) |
One-way from | $169 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $526 |
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 May 10, 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
Quickest round-trip
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sat 9/19
6:00 am-11:54 am
1 stop6h 54m
San José Juan Santamaria Intl
Sat 9/26
1:25 pm-9:46 pm
1 stop7h 21m
$566
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sat 8/22
10:25 am-6:00 pm
1 stop8h 35m
San José Juan Santamaria Intl
Sun 9/6
9:00 am-9:50 pm
1 stop11h 50m
$567
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sat 7/25
5:05 am-11:00 am
1 stop6h 55m
San José Juan Santamaria Intl
Wed 8/12
1:40 pm-11:10 pm
1 stop8h 30m
$581
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Thu 11/5
5:15 am-12:20 pm
1 stop7h 05m
San José Juan Santamaria Intl
Tue 11/10
9:00 am-9:30 pm
2 stops12h 30m
$586
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Thu 8/13
10:05 am-6:40 pm
2 stops9h 35m
San José Juan Santamaria Intl
Sun 8/23
9:00 am-9:20 pm
1 stop11h 20m
$587
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Fri 7/24
6:00 am-11:51 am
1 stop6h 51m
San José Juan Santamaria Intl
Thu 8/20
1:14 pm-10:36 pm
1 stop8h 22m
$720
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Tue 6/9
6:00 am-11:54 am
1 stop6h 54m
San José Juan Santamaria Intl
Tue 6/16
1:19 pm-10:17 pm
1 stop7h 58m
$720
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Thu 5/28
10:15 am-7:00 pm
1 stop9h 45m
San José Juan Santamaria Intl
Mon 6/1
9:00 am-8:15 pm
2 stops10h 15m
$721
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sat 7/25
6:00 am-11:51 am
1 stop6h 51m
San José Juan Santamaria Intl
Mon 8/17
1:14 pm-9:17 am
2 stops19h 03m
$725
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sat 5/23
7:50 am-7:00 pm
2 stops12h 10m
San José Juan Santamaria Intl
Sat 5/30
9:00 am-8:25 pm
1 stop10h 25m
$735
Showing 1-10 of 21 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 May.
| 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 May 10, 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.
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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
Monteverde
Jacó
Heredia
Dominical
Manuel Antonio
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Midway and San José flights
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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 May 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$394 | Average$552 | FlexibilityNo cancel fee | On-time63% |