$136+ 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 4/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
Mar 13 — Mar 201
1 adult, Economy
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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 February 11, 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 February 11, 2026.
This Delta deal was found by Cheapflights users on 2/9. 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.
Tue 3/312:45 pm
MDW
- SJO
1 stop9h 17m
Delta
Tue 3/107:00 am
SJO
- MDW
1 stop14h 31m
Delta
Deal found 2/9![Delta logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/244:33 pm
MDW
- SJO
1 stop19h 09m
Multiple Airlines
Thu 4/911:38 am
SJO
- MDW
2 stops27h 21m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$342
This Ovago deal was found by Cheapflights users on 2/7. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/226:00 am
MDW
- SJO
1 stop16h 02m
LATAM Airlines
Wed 3/47:00 am
SJO
- MDW
1 stop15h 31m
LATAM Airlines
Deal found 2/7![LATAM Airlines logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/62:41 pm
MDW
- SJO
2 stops21h 41m
Multiple Airlines
Mon 3/911:35 am
SJO
- MDW
1 stop8h 18m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$347
This Delta deal was found by Cheapflights users on 2/9. 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.
Mon 3/26:00 am
MDW
- SJO
1 stop16h 02m
Delta
Sat 3/77:00 am
SJO
- MDW
1 stop8h 21m
Delta
Deal found 2/9![Delta logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/72:56 pm
MDW
- SJO
1 stop19h 44m
Multiple Airlines
Mon 3/1611:38 am
SJO
- MDW
1 stop8h 15m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/412:45 pm
MDW
- SJO
1 stop9h 17m
Delta
Sat 3/77:00 am
SJO
- MDW
1 stop15h 31m
Delta
Deal found 2/9![Delta logo]()
$358
This Delta deal was found by Cheapflights users on 2/9. 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.
Mon 3/29:34 am
MDW
- SJO
2 stops12h 28m
Delta
Fri 3/67:00 am
SJO
- MDW
1 stop15h 31m
Delta
Deal found 2/9![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 2/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
MDW
- SJO
1 stop7h 10m
Southwest
Wed 5/131:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Deal found 2/10![Southwest logo]()
$361
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 February 11, 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 February 11, 2026.
This Delta deal was found by Cheapflights users on 2/9. 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.
Sun 3/86:00 am
MDW
- SJO
1 stop16h 15m
Delta
Wed 3/187:00 am
SJO
- MDW
1 stop14h 31m
Delta
Deal found 2/9![Delta logo]()
$348
This Southwest deal was found by Cheapflights users on 2/9. 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 3/106:00 am
MDW
- SJO
1 stop7h 55m
Southwest
Tue 3/171:55 pm
SJO
- MDW
1 stop9h 00m
Southwest
Deal found 2/9![Southwest logo]()
$359
This Delta deal was found by Cheapflights users on 2/9. 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 2/276:00 am
MDW
- SJO
1 stop16h 02m
Delta
Sat 3/77:00 am
SJO
- MDW
1 stop8h 21m
Delta
Deal found 2/9![Delta logo]()
$358
This Delta deal was found by Cheapflights users on 2/9. 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.
Sun 3/16:00 am
MDW
- SJO
1 stop16h 02m
Delta
Fri 3/67:00 am
SJO
- MDW
1 stop15h 31m
Delta
Deal found 2/9![Delta logo]()
$365
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/235:30 am
MDW
- SJO
1 stop7h 20m
Southwest
Thu 2/261:50 pm
SJO
- MDW
1 stop8h 25m
Southwest
Deal found 2/9![Southwest logo]()
$458
This Delta deal was found by Cheapflights users on 2/9. 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 3/66:00 am
MDW
- SJO
1 stop16h 02m
Delta
Wed 3/187:00 am
SJO
- MDW
2 stops9h 54m
Delta
Deal found 2/9![Delta logo]()
$381
This Delta deal was found by Cheapflights users on 2/10. 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.
Tue 3/246:00 am
MDW
- SJO
1 stop16h 15m
Delta
Mon 4/61:20 pm
SJO
- MDW
2 stops27h 34m
Delta
Deal found 2/10![Delta logo]()
$393
This Delta deal was found by Cheapflights users on 2/9. 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.
Mon 3/29:34 am
MDW
- SJO
2 stops12h 28m
Delta
Mon 3/97:00 am
SJO
- MDW
1 stop14h 31m
Delta
Deal found 2/9![Delta logo]()
$422
This Delta deal was found by Cheapflights users on 2/9. 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.
Tue 3/39:34 am
MDW
- SJO
2 stops12h 28m
Delta
Thu 3/191:20 pm
SJO
- MDW
2 stops18h 33m
Delta
Deal found 2/9![Delta logo]()
$433
This Delta deal was found by Cheapflights users on 2/10. 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.
Tue 3/1710:45 am
MDW
- SJO
1 stop11h 30m
Delta
Wed 3/257:00 am
SJO
- MDW
2 stops9h 54m
Delta
Deal found 2/10![Delta logo]()
$443
This Delta deal was found by Cheapflights users on 2/10. 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 2/216:00 am
MDW
- SJO
1 stop16h 02m
Delta
Tue 2/247:00 am
SJO
- MDW
1 stop15h 33m
Delta
Deal found 2/10![Delta logo]()
$444
This Delta deal was found by Cheapflights users on 2/9. 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 3/66:00 am
MDW
- SJO
1 stop16h 02m
Delta
Thu 3/191:20 pm
SJO
- MDW
2 stops18h 33m
Delta
Deal found 2/9![Delta logo]()
$444
Last-minute flights from Midway to San JoséDiscover last-minute flight deals from Midway to San José. Data last updated February 11, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San José. Data last updated February 11, 2026 and is based on user searches.
This Ovago deal was found by Cheapflights users on 2/7. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/226:00 am
MDW
- SJO
1 stop16h 02m
LATAM Airlines
Wed 3/47:00 am
SJO
- MDW
1 stop15h 31m
LATAM Airlines
Deal found 2/7![LATAM Airlines logo]()
$343
This Delta deal was found by Cheapflights users on 2/9. 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.
Mon 3/212:45 pm
MDW
- SJO
1 stop9h 17m
Delta
Wed 3/187:00 am
SJO
- MDW
1 stop14h 31m
Delta
Deal found 2/9![Delta logo]()
$348
This Delta deal was found by Cheapflights users on 2/9. 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.
Mon 3/29:34 am
MDW
- SJO
2 stops12h 28m
Delta
Sat 3/77:00 am
SJO
- MDW
1 stop8h 21m
Delta
Deal found 2/9![Delta logo]()
$353
This Delta deal was found by Cheapflights users on 2/9. 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.
Mon 3/29:34 am
MDW
- SJO
2 stops12h 28m
Delta
Fri 3/67:00 am
SJO
- MDW
1 stop15h 31m
Delta
Deal found 2/9![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 2/9. 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.
Tue 3/312:45 pm
MDW
- SJO
1 stop9h 17m
Delta
Tue 3/107:00 am
SJO
- MDW
1 stop14h 31m
Delta
Deal found 2/9![Delta logo]()
$337
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/412:45 pm
MDW
- SJO
1 stop9h 17m
Delta
Sat 3/77:00 am
SJO
- MDW
1 stop15h 31m
Delta
Deal found 2/9![Delta logo]()
$358
This Delta deal was found by Cheapflights users on 2/10. 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.
Thu 3/510:49 am
MDW
- SJO
1 stop11h 13m
Delta
Wed 3/117:00 am
SJO
- MDW
1 stop14h 31m
Delta
Deal found 2/10![Delta logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/62:41 pm
MDW
- SJO
2 stops21h 41m
Multiple Airlines
Mon 3/911:35 am
SJO
- MDW
1 stop8h 18m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/72:56 pm
MDW
- SJO
1 stop19h 44m
Multiple Airlines
Mon 3/1611:38 am
SJO
- MDW
1 stop8h 15m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/244:33 pm
MDW
- SJO
1 stop19h 09m
Multiple Airlines
Thu 4/911:38 am
SJO
- MDW
2 stops27h 21m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$342
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 February 11, 2026.
Search for one-way flight options from Midway to San José. Find affordable one-way fares based on user searches. Data last updated February 11, 2026.
This Trip.com deal was found by Cheapflights users on 2/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:30 pm
MDW
- SJO
1 stop13h 31m
Frontier
Deal found 2/9![Frontier logo]()
$136
This Trip.com deal was found by Cheapflights users on 2/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:15 am
MDW
- SJO
1 stop9h 15m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 2/257:00 am
MDW
- SJO
3 stops28h 40m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/76:00 am
MDW
- SJO
2 stops29h 22m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Mon 3/169:51 pm
MDW
- SJO
1 stop13h 51m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$167
This Delta deal was found by Cheapflights users on 2/8. 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.
Mon 2/2312:45 pm
MDW
- SJO
1 stop9h 17m
Delta
Deal found 2/8![Delta logo]()
$168
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/259:34 am
MDW
- SJO
2 stops12h 28m
Delta
Deal found 2/9![Delta logo]()
$173
This Trip.com deal was found by Cheapflights users on 2/8. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:15 am
MDW
- SJO
1 stop9h 15m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 2/246:10 am
MDW
- SJO
3 stops28h 28m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$191
This Trip.com deal was found by Cheapflights users on 2/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:00 am
MDW
- SJO
1 stop9h 17m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$204
This KAYAK deal was found by Cheapflights users on 2/9. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/166:00 am
MDW
- SJO
1 stop16h 02m
LATAM Airlines
Deal found 2/9![LATAM Airlines logo]()
$208
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 February 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $337 (Delta) |
One-way from | $136 (Trip.com) |
Popular in | December |
Cheapest in | September |
Average price | $473 |
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 February 11, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San José that are best for you.
Fly from
Midway
Fly to
San José
Route
Depart
Return
Price
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sun 3/8
6:00 am-9:15 pm
1 stop16h 15m
San José Juan Santamaria Intl
Wed 3/18
7:00 am-10:31 pm
1 stop14h 31m
$348
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Fri 2/27
6:00 am-10:02 pm
1 stop16h 02m
San José Juan Santamaria Intl
Sat 3/7
7:00 am-3:21 pm
1 stop8h 21m
$358
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Tue 3/10
6:00 am-12:55 pm
1 stop7h 55m
San José Juan Santamaria Intl
Tue 3/17
1:55 pm-11:55 pm
1 stop9h 00m
$359
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sun 3/1
6:00 am-10:02 pm
1 stop16h 02m
San José Juan Santamaria Intl
Fri 3/6
7:00 am-10:31 pm
1 stop15h 31m
$365
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Fri 3/6
6:00 am-10:02 pm
1 stop16h 02m
San José Juan Santamaria Intl
Wed 3/18
7:00 am-5:54 pm
2 stops9h 54m
$381
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Tue 3/24
6:00 am-9:15 pm
1 stop16h 15m
San José Juan Santamaria Intl
Mon 4/6
1:20 pm-5:54 pm
2 stops27h 34m
$393
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Mon 3/2
9:34 am-10:02 pm
2 stops12h 28m
San José Juan Santamaria Intl
Mon 3/9
7:00 am-10:31 pm
1 stop14h 31m
$422
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Tue 3/3
9:34 am-10:02 pm
2 stops12h 28m
San José Juan Santamaria Intl
Thu 3/19
1:20 pm-8:53 am
2 stops18h 33m
$433
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Tue 3/17
10:45 am-9:15 pm
1 stop11h 30m
San José Juan Santamaria Intl
Wed 3/25
7:00 am-5:54 pm
2 stops9h 54m
$443
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sat 2/21
6:00 am-10:02 pm
1 stop16h 02m
San José Juan Santamaria Intl
Tue 2/24
7:00 am-10:33 pm
1 stop15h 33m
$444
Showing 1-10 of 22 results
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 February.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | 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.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to San José
How often are flights from Chicago to San José delayed?
About 100% of weekly flights between Chicago and San José have experienced delays in the past year, with the average delay time being 97 minutes.
What is the most punctual flight time for Chicago to San José flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
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 February 11, 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.
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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 February 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$394 | Average$575 | FlexibilityNo cancel fee | On-time63% |