$168+ Cheap flights from Chicago (CHI) to San José (SJO)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
Oct 17 — Oct 241
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 October or February, booked 6 days in advance, depart on a Tuesday or Monday and return on a Friday
Cheap flight deals from Chicago to San José
Cheapest
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 September 17, 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 September 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/233:20 pm -
1 stop18h 44m
Fri 10/3010:03 am -
1 stop14h 02m
Deal found 9/13![Copa Airlines logo]()
$379
This Booking.com deal was found by Cheapflights users on 9/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/313:13 pm -
1 stop18h 06m
Sat 11/710:03 am -
1 stop14h 08m
Deal found 9/14![Copa Airlines logo]()
$381
This Avianca deal was found by Cheapflights users on 9/16. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2111:20 pm -
1 stop17h 05m
Sat 10/241:55 am -
1 stop18h 35m
Deal found 9/16![Avianca logo]()
$384
This Copa Airlines deal was found by Cheapflights users on 9/14. 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.
Mon 11/22:13 pm -
1 stop20h 46m
Thu 11/125:55 pm -
1 stop18h 51m
Deal found 9/14![Copa Airlines logo]()
$386
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:49 pm -
1 stop18h 18m
Wed 11/113:54 pm -
1 stop17h 38m
Deal found 9/15![American Airlines logo]()
$398
This Mytrip deal was found by Cheapflights users on 9/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2011:20 pm -
1 stop10h 30m
Tue 10/275:15 pm -
1 stop27h 15m
Deal found 9/15![Avianca logo]()
$402
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/49:06 pm -
1 stop16h 01m
Sun 11/153:54 pm -
1 stop8h 50m
Deal found 9/15![American Airlines logo]()
$403
This Avianca deal was found by Cheapflights users on 9/16. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/110:30 pm -
1 stop10h 20m
Sat 11/71:55 am -
1 stop18h 35m
Deal found 9/16![Avianca logo]()
$404
This Copa Airlines deal was found by Cheapflights users on 9/16. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/22:13 pm -
1 stop20h 46m
Wed 11/43:59 am -
1 stop20h 12m
Deal found 9/16![Copa Airlines logo]()
$406
This Justfly.com deal was found by Cheapflights users on 9/16. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/310:30 pm -
1 stop17h 50m
Tue 11/109:30 am -
1 stop11h 00m
Deal found 9/16![Avianca logo]()
$407
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:04 am -
1 stop6h 56m
Wed 11/42:25 pm -
2 stops19h 07m
Deal found 9/14![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 9/12. 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 11/156:00 am -
1 stop16h 15m
Wed 12/27:00 am -
1 stop9h 17m
Deal found 9/12![Delta logo]()
$418
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 September 17, 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 September 17, 2026.
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/2012:40 pm -
1 stop7h 59m
Mon 1/251:15 am -
1 stop11h 34m
Deal found 9/15![United Airlines logo]()
$398
This Copa Airlines deal was found by Cheapflights users on 9/14. 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.
Wed 10/73:20 pm -
1 stop16h 50m
Mon 10/1210:03 am -
1 stop13h 54m
Deal found 9/14![Copa Airlines logo]()
$473
This Delta deal was found by Cheapflights users on 9/12. 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.
Wed 11/181:05 pm -
1 stop9h 10m
Wed 12/22:37 pm -
2 stops19h 00m
Deal found 9/12![Delta logo]()
$500
This Southwest deal was found by Cheapflights users on 9/14. 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.
Sun 2/285:00 am -
1 stop8h 45m
Sat 3/62:45 pm -
1 stop7h 45m
Deal found 9/14![Southwest logo]()
$599
This United Airlines deal was found by Cheapflights users on 9/12. 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.
Wed 1/207:02 am -
Nonstop5h 13m
Sun 1/241:15 am -
1 stop10h 01m
Deal found 9/12![United Airlines logo]()
$435
This Copa Airlines deal was found by Cheapflights users on 9/16. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/72:13 pm -
1 stop17h 09m
Wed 1/136:02 pm -
1 stop18h 44m
Deal found 9/16![Copa Airlines logo]()
$483
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/247:02 am -
Nonstop5h 13m
Sat 1/301:15 am -
1 stop10h 01m
Deal found 9/14![United Airlines logo]()
$472
This Delta deal was found by Cheapflights users on 9/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:04 am -
1 stop6h 56m
Mon 11/92:37 pm -
1 stop8h 17m
Deal found 9/16![Delta logo]()
$559
This Delta deal was found by Cheapflights users on 9/15. 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.
Sat 12/126:49 am -
1 stop15h 28m
Mon 12/217:00 am -
2 stops13h 46m
Deal found 9/15![Delta logo]()
$564
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/227:02 am -
Nonstop5h 13m
Thu 3/41:25 pm -
Nonstop5h 32m
Deal found 9/15![United Airlines logo]()
$524
This Southwest deal was found by Cheapflights users on 9/15. 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.
Tue 10/2012:25 pm -
1 stop8h 15m
Sun 10/251:35 pm -
1 stop10h 25m
Deal found 9/15![Southwest logo]()
$656
This Delta deal was found by Cheapflights users on 9/15. 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.
Tue 12/111:28 am -
1 stop10h 49m
Wed 12/97:00 am -
1 stop9h 17m
Deal found 9/15![Delta logo]()
$569
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/277:30 am -
1 stop13h 07m
Wed 3/31:25 pm -
Nonstop5h 32m
Deal found 9/15![United Airlines logo]()
$545
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/75:52 pm -
1 stop12h 33m
Sat 11/141:55 pm -
Nonstop5h 33m
Deal found 9/14![United Airlines logo]()
$548
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/59:30 am -
2 stops12h 35m
Wed 1/207:05 am -
2 stops11h 32m
Deal found 9/14![Delta logo]()
$621
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Tue 1/1912:40 pm -
1 stop7h 59m
Wed 1/278:45 am -
2 stops12h 46m
Deal found 9/17![United Airlines logo]()
$558
This Delta deal was found by Cheapflights users on 9/15. 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.
Wed 1/209:30 am -
2 stops12h 35m
Tue 1/262:10 pm -
1 stop8h 00m
Deal found 9/15![Delta logo]()
$621
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/149:30 am -
2 stops12h 35m
Thu 1/217:05 am -
1 stop9h 20m
Deal found 9/14![Delta logo]()
$621
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/157:02 am -
Nonstop5h 13m
Tue 1/198:45 am -
1 stop12h 50m
Deal found 9/16![United Airlines logo]()
$568
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/126:50 am -
1 stop11h 26m
Thu 2/182:25 pm -
1 stop9h 30m
Deal found 9/15![United Airlines logo]()
$575
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/129:30 am -
2 stops12h 35m
Tue 1/197:05 am -
1 stop15h 05m
Deal found 9/14![Delta logo]()
$697
This Delta deal was found by Cheapflights users on 9/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/296:00 am -
1 stop6h 45m
Sat 2/67:05 am -
1 stop9h 20m
Deal found 9/13![Delta logo]()
$720
This Delta deal was found by Cheapflights users on 9/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2110:35 am -
1 stop11h 30m
Mon 1/252:10 pm -
1 stop8h 00m
Deal found 9/13![Delta logo]()
$720
Last-minute flights from Chicago to San JoséDiscover last-minute flight deals from Chicago to San José. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San José. Data last updated September 17, 2026 and is based on user searches.
This Copa Airlines deal was found by Cheapflights users on 9/12. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/123:20 pm -
1 stop18h 44m
Mon 10/194:08 am -
1 stop19h 49m
Deal found 9/12![Copa Airlines logo]()
$406
This Mytrip deal was found by Cheapflights users on 9/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2011:20 pm -
1 stop10h 30m
Tue 10/275:15 pm -
1 stop27h 15m
Deal found 9/15![Avianca logo]()
$402
This Avianca deal was found by Cheapflights users on 9/16. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2111:20 pm -
1 stop17h 05m
Sat 10/241:55 am -
1 stop18h 35m
Deal found 9/16![Avianca logo]()
$384
This Avianca deal was found by Cheapflights users on 9/14. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:20 pm -
1 stop10h 30m
Sun 10/251:50 am -
1 stop18h 40m
Deal found 9/14![Avianca logo]()
$404
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/233:20 pm -
1 stop18h 44m
Fri 10/3010:03 am -
1 stop14h 02m
Deal found 9/13![Copa Airlines logo]()
$379
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/249:45 pm -
1 stop13h 40m
Sat 10/311:05 pm -
Nonstop5h 33m
Deal found 9/14![United Airlines logo]()
$408
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:04 am -
1 stop6h 56m
Sun 11/12:25 pm -
1 stop8h 08m
Deal found 9/14![Delta logo]()
$465
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:30 am -
1 stop7h 52m
Wed 11/48:45 am -
1 stop9h 45m
Deal found 9/14![United Airlines logo]()
$398
This American Airlines deal was found by Cheapflights users on 9/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/289:29 pm -
1 stop17h 31m
Sun 11/16:20 am -
1 stop13h 29m
Deal found 9/16![American Airlines logo]()
$403
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:04 am -
1 stop6h 56m
Wed 11/42:25 pm -
2 stops19h 07m
Deal found 9/14![Delta logo]()
$409
This Copa Airlines deal was found by Cheapflights users on 9/14. 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 10/303:13 pm -
1 stop18h 06m
Thu 11/52:18 pm -
1 stop22h 28m
Deal found 9/14![Copa Airlines logo]()
$386
This Booking.com deal was found by Cheapflights users on 9/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/313:13 pm -
1 stop18h 06m
Sat 11/710:03 am -
1 stop14h 08m
Deal found 9/14![Copa Airlines logo]()
$381
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 September 17, 2026.
Search for one-way flight options from Chicago to San José. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This Jetabroad deal was found by Cheapflights users on 9/13. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2812:53 pm -
1 stop11h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Multiple Airlines logo]()
$168
This FlightHub deal was found by Cheapflights users on 9/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/912:53 pm -
1 stop11h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$173
This Southwest deal was found by Cheapflights users on 9/16. 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.
Mon 2/15:25 am -
1 stop8h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$178
This Jetabroad deal was found by Cheapflights users on 9/15. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/1412:53 pm -
1 stop11h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$179
This Jetabroad deal was found by Cheapflights users on 9/12. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1112:53 pm -
1 stop11h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Multiple Airlines logo]()
$181
This FlightHub deal was found by Cheapflights users on 9/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/212:53 pm -
1 stop11h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$186
This Southwest deal was found by Cheapflights users on 9/13. 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 -
1 stop7h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Southwest logo]()
$188
This Southwest deal was found by Cheapflights users on 9/13. 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 2/288:20 pm -
2 stops17h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Southwest logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/22:41 am -
2 stops22h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$211
This Southwest deal was found by Cheapflights users on 9/16. 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 10/259:55 am -
2 stops10h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$215
This Jetabroad deal was found by Cheapflights users on 9/16. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/251:49 pm -
1 stop11h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$222
This Southwest deal was found by Cheapflights users on 9/13. 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 -
1 stop7h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Southwest logo]()
$225
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 September 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $379 (Kiwi.com) |
One-way from | $168 (Jetabroad) |
Popular in | December |
Cheapest in | October |
Average price | $505 |
Good round-trip deal | $527 or less |
Good one-way deal | $393 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 7,457,451 searches. Data last updated September 17, 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 Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Mon 2/1
5:25 am-1:45 pm
1 stop8h 20m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$178
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Sun 11/1
5:15 am-12:20 pm
1 stop7h 05m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$188
ChicagoSan José
ORD Chicago O'Hare Intl - SJO San José Juan Santamaria Intl
ORDSJO
Chicago O'Hare Intl
Tue 2/2
12:53 pm-11:59 pm
1 stop11h 06m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$206
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Sun 2/28
8:20 pm-1:45 pm
2 stops17h 25m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$210
ChicagoSan José
ORD Chicago O'Hare Intl - SJO San José Juan Santamaria Intl
ORDSJO
Chicago O'Hare Intl
Tue 10/27
1:55 pm-10:50 pm
1 stop9h 55m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$286
ChicagoSan José
ORD Chicago O'Hare Intl - SJO San José Juan Santamaria Intl
ORDSJO
Chicago O'Hare Intl
Tue 10/27
7:50 pm-12:15 pm
3 stops41h 25m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$286
ChicagoSan José
ORD Chicago O'Hare Intl - SJO San José Juan Santamaria Intl
ORDSJO
Chicago O'Hare Intl
Sun 11/1
8:45 am-11:50 pm
2 stops15h 05m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$310
ChicagoSan José
ORD Chicago O'Hare Intl - SJO San José Juan Santamaria Intl
ORDSJO
Chicago O'Hare Intl
Thu 10/1
1:49 pm-11:59 pm
1 stop11h 10m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$321
ChicagoSan José
ORD Chicago O'Hare Intl - SJO San José Juan Santamaria Intl
ORDSJO
Chicago O'Hare Intl
Tue 12/1
6:29 am-11:02 am
3 stops28h 33m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$347
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Mon 2/1
6:17 pm-10:15 pm
2 stops27h 58m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$369
Showing 1-10 of 44 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 September.
| 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
ORD-SJO
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 to San José
CHI-SJO
ORD-SJO
MDW-SJO
What is the cheapest month to book a flight from Chicago to San José?
Currently, October is the cheapest month in which you can book a flight from Chicago to San José (average of $463). Flying from Chicago to San José in December is currently the most expensive (average of $670). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Chicago to San José?
Airfare is typical for this route at the moment.
Chicago to San José flights typically cost between $300 and $569 in October.The cheapest round-trip price found within the last 5 days was $379 on Copa Airlines (Oct 23-Oct 30).
How often are flights from Chicago to San José delayed?
About 20% of weekly flights between Chicago and San José have experienced delays in the past year, with the average delay time being 149 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 15% 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 5 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 September 17, 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.
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
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
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Chicago
Popular flights
San José flight routes
Alternative routes for Chicago to San José
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to San José by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to San José by cabin class
Find flights from Chicago to San José, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and San José flights
Browse other Chicago and San José flight options. Last updated on September 17, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on September 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to San José
Explore flights to San José departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 17, 2026.
Top 9 airlines flying from Chicago to San José
Discover the top 9 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 7,457,451 searches. Data last updated September 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$148 | Average$640 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$200 | Average$446 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$303 | Average$504 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$336 | Average$544 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$380 | Average$596 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$384 | Average$740 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$390 | Average$596 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$395 | Average$649 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$551 | Average$650 | FlexibilityNo cancel fee | On-time67% |