$120+ Cheap flights from Chicago (CHI) 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 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
Aug 15 — Aug 221
Round-trip
1 adult, Economy
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Find cheap flights from Chicago 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.Cheapflights Tip: The best prices from Chicago to San José Juan Santamaria Intl are usually found in September or October, booked 9 days in advance, depart on a Tuesday or Wednesday and return on a Thursday
Cheap flight deals from Chicago to San José
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Best
Last-minute
One-way
Cheapest flights from Chicago to San JoséExplore the most affordable flight options available from Chicago to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 16, 2026.
Explore the most affordable flight options available from Chicago to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 16, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/214:20 pm
ORD
- SJO
1 stop20h 55m
Multiple Airlines
Sun 10/251:33 pm
SJO
- ORD
2 stops15h 10m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$493
This Southwest deal was found by Cheapflights users on 7/15. 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 8/2810:05 am
MDW
- SJO
1 stop9h 35m
Southwest
Thu 9/101:40 pm
SJO
- MDW
1 stop7h 35m
Southwest
Deal found 7/15![Southwest logo]()
$494
This Kiwi.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/74:20 pm
ORD
- SJO
1 stop20h 55m
Multiple Airlines
Mon 10/197:07 am
SJO
- ORD
1 stop15h 48m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$495
This Kiwi.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/311:30 am
ORD
- SJO
1 stop24h 50m
Viva
Fri 8/142:20 am
SJO
- ORD
1 stop21h 20m
Viva
Deal found 7/14![Viva logo]()
$496
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1410:05 am
MDW
- SJO
2 stops10h 35m
Southwest
Wed 10/289:00 am
SJO
- MDW
2 stops9h 40m
Southwest
Deal found 7/13![Southwest logo]()
$497
This Kiwi.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:35 am
ORD
- SJO
1 stop9h 20m
Multiple Airlines
Thu 10/151:15 pm
SJO
- ORD
1 stop22h 55m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$497
This Southwest deal was found by Cheapflights users on 7/15. 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 10/2211:50 am
MDW
- SJO
1 stop8h 50m
Southwest
Mon 10/261:30 pm
SJO
- MDW
2 stops10h 35m
Southwest
Deal found 7/15![Southwest logo]()
$498
This Kiwi.com deal was found by Cheapflights users on 7/15. 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.
Thu 10/156:05 am
ORD
- SJO
1 stop10h 06m
Multiple Airlines
Fri 10/237:07 am
SJO
- ORD
2 stops12h 21m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$498
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/111:50 am
MDW
- SJO
1 stop8h 50m
Southwest
Mon 10/59:00 am
SJO
- MDW
2 stops10h 10m
Southwest
Deal found 7/14![Southwest logo]()
$499
This Cheapflightsfares deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Wed 9/22:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Deal found 7/14![JetBlue logo]()
$499
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/304:20 pm
ORD
- SJO
1 stop21h 00m
Multiple Airlines
Sat 9/57:00 am
SJO
- ORD
1 stop27h 00m
Multiple Airlines
Deal found 7/11![Multiple Airlines logo]()
$500
This Southwest deal was found by Cheapflights users on 7/15. 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 10/217:40 am
MDW
- SJO
2 stops13h 00m
Southwest
Sun 10/259:00 am
SJO
- MDW
2 stops11h 50m
Southwest
Deal found 7/15![Southwest logo]()
$501
Best flights from Chicago to San JoséDiscover carefully curated flight deals from Chicago to San José that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 16, 2026.
Discover carefully curated flight deals from Chicago to San José that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 16, 2026.
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/111:05 am
MDW
- SJO
2 stops9h 35m
Southwest
Mon 10/59:00 am
SJO
- MDW
2 stops10h 10m
Southwest
Deal found 7/14![Southwest logo]()
$503
This Volaris deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/102:53 am
ORD
- SJO
1 stop22h 06m
Multiple Airlines
Tue 8/184:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$543
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/205:30 am
ORD
- SJO
1 stop7h 24m
Delta
Thu 9/241:19 pm
SJO
- ORD
2 stops17h 38m
Delta
Deal found 7/12![Delta logo]()
$616
This JetBlue deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/317:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Mon 9/72:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Deal found 7/11![JetBlue logo]()
$636
This Copa Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/283:21 pm
ORD
- SJO
1 stop16h 49m
Copa Airlines
Fri 9/44:08 am
SJO
- ORD
1 stop19h 54m
Copa Airlines
Deal found 7/14![Copa Airlines logo]()
$637
This United Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:30 am
ORD
- SJO
1 stop13h 07m
United Airlines
Mon 9/281:25 pm
SJO
- ORD
1 stop9h 58m
United Airlines
Deal found 7/12![United Airlines logo]()
$642
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2710:05 am
MDW
- SJO
1 stop9h 35m
Southwest
Wed 9/29:00 am
SJO
- MDW
1 stop9h 15m
Southwest
Deal found 7/11![Southwest logo]()
$511
This Volaris deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/32:53 am
ORD
- SJO
1 stop22h 06m
Multiple Airlines
Tue 8/114:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$549
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:20 am
MDW
- SJO
1 stop13h 20m
Southwest
Fri 10/169:00 am
SJO
- MDW
2 stops10h 10m
Southwest
Deal found 7/13![Southwest logo]()
$512
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/305:20 pm
ORD
- SJO
2 stops19h 29m
Delta
Sun 9/61:14 pm
SJO
- ORD
1 stop9h 43m
Delta
Deal found 7/11![Delta logo]()
$616
This Southwest deal was found by Cheapflights users on 7/15. 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 8/2610:10 am
MDW
- SJO
2 stops9h 30m
Southwest
Wed 9/29:00 am
SJO
- MDW
2 stops11h 50m
Southwest
Deal found 7/15![Southwest logo]()
$546
This United Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:25 am
ORD
- SJO
1 stop14h 12m
United Airlines
Thu 10/157:55 am
SJO
- ORD
1 stop15h 28m
United Airlines
Deal found 7/13![United Airlines logo]()
$677
This Delta deal was found by Cheapflights users on 7/15. 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 10/125:30 am
ORD
- SJO
1 stop7h 28m
Delta
Mon 10/191:23 pm
SJO
- ORD
2 stops17h 40m
Delta
Deal found 7/15![Delta logo]()
$626
This Volaris deal was found by Cheapflights users on 7/16. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/266:21 am
ORD
- SJO
1 stop18h 38m
Multiple Airlines
Tue 8/44:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$634
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2810:05 am
MDW
- SJO
2 stops9h 35m
Southwest
Fri 9/49:00 am
SJO
- MDW
1 stop11h 30m
Southwest
Deal found 7/14![Southwest logo]()
$557
This Volaris deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/281:49 pm
ORD
- SJO
1 stop11h 10m
Multiple Airlines
Tue 8/44:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$634
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:00 am
MDW
- SJO
1 stop6h 58m
Delta
Wed 10/141:23 pm
SJO
- MDW
1 stop8h 02m
Delta
Deal found 7/12![Delta logo]()
$691
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2310:15 am
MDW
- SJO
2 stops9h 25m
Southwest
Thu 8/279:00 am
SJO
- MDW
1 stop8h 00m
Southwest
Deal found 7/11![Southwest logo]()
$637
This Delta deal was found by Cheapflights users on 7/15. 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 8/176:05 am
MDW
- SJO
1 stop6h 44m
Delta
Wed 8/191:14 pm
SJO
- MDW
1 stop8h 22m
Delta
Deal found 7/15![Delta logo]()
$701
This Southwest deal was found by Cheapflights users on 7/15. 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 9/38:00 am
MDW
- SJO
2 stops11h 40m
Southwest
Sun 9/69:00 am
SJO
- MDW
2 stops9h 25m
Southwest
Deal found 7/15![Southwest logo]()
$652
Last-minute flights from Chicago to San JoséDiscover last-minute flight deals from Chicago to San José. Data last updated July 16, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San José. Data last updated July 16, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/311:30 am
ORD
- SJO
1 stop24h 50m
Viva
Fri 8/142:20 am
SJO
- ORD
1 stop21h 20m
Viva
Deal found 7/14![Viva logo]()
$496
This Kiwi.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/71:30 am
ORD
- SJO
1 stop24h 50m
Viva
Thu 8/201:20 pm
SJO
- ORD
1 stop24h 30m
Viva
Deal found 7/13![Viva logo]()
$503
This CheapOair deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/85:13 pm
ORD
- SJO
1 stop16h 07m
Frontier
Thu 8/139:35 am
SJO
- ORD
1 stop12h 35m
Frontier
Deal found 7/14![Frontier logo]()
$508
This Cheapflightsfares deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Mon 8/312:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Deal found 7/14![JetBlue logo]()
$499
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:00 am
ORD
- SJO
1 stop8h 52m
American Airlines
Tue 9/11:03 pm
SJO
- ORD
1 stop10h 15m
American Airlines
Deal found 7/13![American Airlines logo]()
$502
This Southwest deal was found by Cheapflights users on 7/15. 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 8/2810:05 am
MDW
- SJO
1 stop9h 35m
Southwest
Thu 9/101:40 pm
SJO
- MDW
1 stop7h 35m
Southwest
Deal found 7/15![Southwest logo]()
$494
This Southwest deal was found by Cheapflights users on 7/16. 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 8/307:55 am
MDW
- SJO
2 stops11h 45m
Southwest
Sun 9/69:00 am
SJO
- MDW
2 stops9h 25m
Southwest
Deal found 7/16![Southwest logo]()
$498
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/304:20 pm
ORD
- SJO
1 stop21h 00m
Multiple Airlines
Sat 9/57:00 am
SJO
- ORD
1 stop27h 00m
Multiple Airlines
Deal found 7/11![Multiple Airlines logo]()
$500
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:42 pm
MDW
- SJO
2 stops18h 07m
Delta
Sun 9/61:14 pm
SJO
- MDW
1 stop8h 22m
Delta
Deal found 7/11![Delta logo]()
$507
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/305:20 pm
ORD
- SJO
2 stops19h 29m
Delta
Sat 9/51:14 pm
SJO
- ORD
1 stop9h 43m
Delta
Deal found 7/11![Delta logo]()
$507
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:05 am
MDW
- SJO
1 stop6h 44m
Delta
Sun 9/61:14 pm
SJO
- MDW
1 stop8h 22m
Delta
Deal found 7/11![Delta logo]()
$502
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:05 am
ORD
- SJO
1 stop10h 06m
Multiple Airlines
Thu 9/101:15 pm
SJO
- ORD
1 stop23h 04m
Multiple Airlines
Deal found 7/11![Multiple Airlines logo]()
$504
One-way flights from Chicago to San JoséSearch for one-way flight options from Chicago to San José. Find affordable one-way fares based on user searches. Data last updated July 16, 2026.
Search for one-way flight options from Chicago to San José. Find affordable one-way fares based on user searches. Data last updated July 16, 2026.
This Viva deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/274:22 pm
ORD
- SJO
1 stop20h 53m
Viva
Deal found 7/14![Viva logo]()
$120
This Cheapflightsfares deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/317:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Deal found 7/13![JetBlue logo]()
$136
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/15:15 am
MDW
- SJO
1 stop7h 05m
Southwest
Deal found 7/13![Southwest logo]()
$138
This Viva deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/21:30 am
ORD
- SJO
1 stop24h 50m
Viva
Deal found 7/11![Viva logo]()
$145
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:15 am
MDW
- SJO
1 stop7h 30m
Southwest
Deal found 7/14![Southwest logo]()
$148
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2210:10 am
MDW
- SJO
2 stops9h 30m
Southwest
Deal found 7/11![Southwest logo]()
$164
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:45 am
MDW
- SJO
1 stop7h 20m
Southwest
Deal found 7/13![Southwest logo]()
$174
This oojo deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/26:21 am
ORD
- SJO
1 stop18h 38m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$196
This Volaris deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/32:53 am
ORD
- SJO
1 stop22h 06m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$198
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:20 am
MDW
- SJO
2 stops11h 20m
Southwest
Deal found 7/11![Southwest logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/147:00 am
ORD
- SJO
3 stops57h 11m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$200
This Justfly.com deal was found by Cheapflights users on 7/15. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:13 pm
ORD
- SJO
1 stop16h 07m
Frontier
Deal found 7/15![Frontier logo]()
$203
Find flight deals from Chicago to San José
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) 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 July 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $493 (Kiwi.com) |
One-way from | $120 (Viva) |
Popular in | December |
Cheapest in | September |
Average price | $633 |
Good round-trip deal | $627 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago 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 July 16, 2026.
Use the filters below to find and compare flights from Chicago 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
Thu 10/1
11:05 am-7:40 pm
2 stops9h 35m
San José Juan Santamaria Intl
Mon 10/5
9:00 am-8:10 pm
2 stops10h 10m
$503
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Thu 8/27
10:05 am-6:40 pm
1 stop9h 35m
San José Juan Santamaria Intl
Wed 9/2
9:00 am-7:15 pm
1 stop9h 15m
$511
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sat 10/10
7:20 am-7:40 pm
1 stop13h 20m
San José Juan Santamaria Intl
Fri 10/16
9:00 am-8:10 pm
2 stops10h 10m
$512
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Mon 8/10
2:53 am-11:59 pm
1 stop22h 06m
San José Juan Santamaria Intl
Tue 8/18
4:15 pm-12:09 pm
1 stop18h 54m
$543
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Wed 8/26
10:10 am-6:40 pm
2 stops9h 30m
San José Juan Santamaria Intl
Wed 9/2
9:00 am-9:50 pm
2 stops11h 50m
$546
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Mon 8/3
2:53 am-11:59 pm
1 stop22h 06m
San José Juan Santamaria Intl
Tue 8/11
4:15 pm-12:09 pm
1 stop18h 54m
$549
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Fri 8/28
10:05 am-6:40 pm
2 stops9h 35m
San José Juan Santamaria Intl
Fri 9/4
9:00 am-9:30 pm
1 stop11h 30m
$557
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sun 9/20
5:30 am-11:54 am
1 stop7h 24m
San José Juan Santamaria Intl
Thu 9/24
1:19 pm-7:57 am
2 stops17h 38m
$616
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sun 8/30
5:20 pm-11:49 am
2 stops19h 29m
San José Juan Santamaria Intl
Sun 9/6
1:14 pm-11:57 pm
1 stop9h 43m
$616
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Mon 10/12
5:30 am-11:58 am
1 stop7h 28m
San José Juan Santamaria Intl
Mon 10/19
1:23 pm-8:03 am
2 stops17h 40m
$626
Showing 1-10 of 36 resultsSorted by cheapest first
Compare providers for flights from Chicago 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 Chicago to San José in July.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Chicago-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-San José flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-San José flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-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-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 Chicago to San José
Have a flexible travel schedule? Discover the best time to fly to San José from Chicago with our price prediction graph.
CHI-SJO
MDW-SJO
ORD-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 to San José
CHI-SJO
MDW-SJO
ORD-SJO
What is the cheapest month to book a flight from Chicago to San José?
Currently, August is the cheapest month in which you can book a flight from Chicago to San José (average of $88). Flying from Chicago to San José in December is currently the most expensive (average of $2,328). 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.
What is the cheapest time of day to fly from CHI to SJO?
Find hourly flight availability from Chicago to San José. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 16, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to San José as you normally would.
How much does it cost to fly round-trip from Chicago to San José?
How often are flights from Chicago to San José delayed?
About 19% of weekly flights between Chicago and San José have experienced delays in the past year, with the average delay time being 160 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 early afternoon tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Saturday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to San José flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 14% of flights being delayed.
How far ahead should I book a flight from Chicago to San José?
The price you pay for your flight from Chicago to San José may vary depending on when you book. For the best chance of a lower fare, look to book 13 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
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 July 16, 2026.
Read through reviews of airlines operating flights from Chicago to San José, such as Southwest,Copa Airlines, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Overall
8.0
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Overall
8.0
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Overall
8.0
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Overall
8.0
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Overall
8.0
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Overall
8.0
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Related info for your journey
Find useful and relevant information for your journey from Chicago 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
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Chicago and San José flights
Browse other Chicago and San José flight options. Last updated on July 16, 2026.
Other flights from Chicago
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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 July 16, 2026.
Top 10 airlines flying from Chicago to San José
Discover the top 10 airlines that operate flights from Chicago 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 July 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$148 | Average$672 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$151 | Average$796 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$221 | Average$482 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$303 | Average$490 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$309 | Average$661 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$339 | Average$553 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$384 | Average$740 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$385 | Average$598 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$386 | Average$591 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$390 | Average$596 | FlexibilityNo cancel fee | On-time62% |