$185+ Cheap flights from San José (SJO) to Chicago (CHI)
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 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
Oct 17 — Oct 241
Round-trip
1 adult, Economy
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Find cheap flights from San José to Chicago 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 San José Juan Santamaria Intl to Chicago are usually found in January or November, booked 90 days in advance, depart on a Friday or Tuesday and return on a Tuesday
Cheap flight deals from San José to Chicago
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Cheapest flights from San José to ChicagoExplore the most affordable flight options available from San José to Chicago. 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 San José to Chicago. 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 9/14. 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 10/216:05 pm -
1 stop29h 52m
Wed 11/42:13 pm -
1 stop18h 54m
Deal found 9/14![Copa Airlines logo]()
$365
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.
Tue 11/177:00 am -
1 stop15h 54m
Fri 11/276:00 am -
1 stop16h 15m
Deal found 9/16![Delta logo]()
$366
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 11/2011:28 pm -
1 stop14h 26m
Wed 11/259:35 pm -
1 stop13h 50m
Deal found 9/16![United Airlines logo]()
$366
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 12/118:45 am -
1 stop14h 11m
Wed 1/67:02 am -
Nonstop5h 13m
Deal found 9/15![United Airlines logo]()
$371
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:05 pm -
1 stop30h 00m
Thu 11/52:13 pm -
1 stop16h 49m
Deal found 9/14![Copa Airlines logo]()
$374
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 10/3011:35 am -
1 stop9h 01m
Wed 11/45:30 pm -
1 stop17h 55m
Deal found 9/16![United Airlines logo]()
$375
This Avianca 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/189:25 am -
1 stop10h 55m
Fri 9/2511:20 pm -
1 stop10h 30m
Deal found 9/15![Avianca logo]()
$376
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.
Wed 12/231:25 pm -
Nonstop5h 32m
Wed 12/309:43 pm -
1 stop24h 49m
Deal found 9/16![United Airlines logo]()
$379
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 10/216:00 am -
1 stop12h 55m
Sat 11/710:55 am -
2 stops9h 55m
Deal found 9/15![American Airlines logo]()
$380
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 10/1410:03 am -
1 stop13h 54m
Sun 10/188:01 am -
1 stop24h 09m
Deal found 9/14![Copa Airlines logo]()
$381
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 10/159:25 am -
1 stop10h 55m
Tue 10/2011:20 pm -
1 stop10h 30m
Deal found 9/14![Avianca logo]()
$382
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:03 am -
1 stop13h 54m
Mon 10/263:13 pm -
1 stop18h 06m
Deal found 9/15![Copa Airlines logo]()
$383
Best flights from San José to ChicagoDiscover carefully curated flight deals from San José to Chicago 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 San José to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 17, 2026.
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.
Tue 11/177:00 am -
1 stop15h 54m
Fri 11/276:00 am -
1 stop16h 15m
Deal found 9/16![Delta logo]()
$366
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 12/211:28 pm -
1 stop14h 55m
Tue 12/87:00 am -
1 stop12h 53m
Deal found 9/15![United Airlines logo]()
$366
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:03 am -
1 stop14h 08m
Wed 11/252:13 pm -
1 stop20h 46m
Deal found 9/15![Copa Airlines logo]()
$402
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.
Sat 10/171:00 pm -
1 stop8h 20m
Sun 10/259:55 am -
2 stops10h 45m
Deal found 9/13![Southwest logo]()
$599
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.
Sat 12/191:25 pm -
Nonstop5h 32m
Fri 1/17:00 am -
1 stop13h 39m
Deal found 9/16![United Airlines logo]()
$382
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.
Wed 11/2511:28 pm -
1 stop12h 02m
Sat 11/287:17 am -
Nonstop5h 18m
Deal found 9/17![United Airlines logo]()
$387
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.
Thu 11/1911:28 pm -
1 stop10h 17m
Wed 11/257:55 pm -
1 stop15h 30m
Deal found 9/14![United Airlines logo]()
$387
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.
Sun 12/275:53 pm -
1 stop18h 53m
Fri 1/112:27 am -
1 stop7h 50m
Deal found 9/16![Copa Airlines logo]()
$476
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 12/212:15 pm -
1 stop26h 39m
Wed 12/309:43 pm -
1 stop24h 49m
Deal found 9/15![United Airlines logo]()
$391
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 12/411:28 pm -
1 stop12h 19m
Tue 12/87:00 am -
1 stop12h 53m
Deal found 9/16![United Airlines logo]()
$405
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 11/197:00 am -
1 stop9h 18m
Wed 11/251:05 pm -
1 stop9h 10m
Deal found 9/16![Delta logo]()
$708
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.
Thu 12/247:30 am -
1 stop12h 30m
Fri 1/19:43 pm -
1 stop24h 49m
Deal found 9/17![United Airlines logo]()
$469
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.
Fri 11/201:20 pm -
1 stop9h 40m
Sun 11/228:25 pm -
2 stops16h 50m
Deal found 9/13![Southwest logo]()
$783
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.
Tue 10/131:25 pm -
1 stop8h 08m
Tue 10/206:04 am -
1 stop6h 56m
Deal found 9/13![Delta logo]()
$755
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.
Wed 1/131:25 pm -
Nonstop5h 32m
Wed 1/205:30 am -
1 stop7h 52m
Deal found 9/14![United Airlines logo]()
$472
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 12/27:00 am -
2 stops11h 01m
Tue 12/89:37 am -
2 stops12h 40m
Deal found 9/15![Delta logo]()
$769
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 10/71:25 pm -
1 stop8h 08m
Tue 10/136:04 am -
1 stop6h 56m
Deal found 9/12![Delta logo]()
$780
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 10/71:25 pm -
1 stop8h 08m
Wed 10/146:04 am -
1 stop6h 56m
Deal found 9/15![Delta logo]()
$819
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.
Sun 12/62:37 pm -
1 stop8h 18m
Tue 12/1511:28 am -
1 stop10h 49m
Deal found 9/15![Delta logo]()
$830
Last-minute flights from San José to ChicagoDiscover last-minute flight deals from San José to Chicago. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from San José to Chicago. Data last updated September 17, 2026 and is based on user searches.
This Avianca 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/189:25 am -
1 stop10h 55m
Fri 9/2511:20 pm -
1 stop10h 30m
Deal found 9/15![Avianca logo]()
$376
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.
Fri 9/251:50 am -
1 stop18h 30m
Tue 9/2911:20 pm -
1 stop10h 30m
Deal found 9/16![Avianca logo]()
$366
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.
Fri 10/94:00 pm -
1 stop28h 20m
Tue 10/1311:20 pm -
1 stop25h 35m
Deal found 9/16![Avianca logo]()
$386
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 10/1410:03 am -
1 stop13h 54m
Sun 10/188:01 am -
1 stop24h 09m
Deal found 9/14![Copa Airlines logo]()
$381
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 10/159:25 am -
1 stop10h 55m
Tue 10/2011:20 pm -
1 stop10h 30m
Deal found 9/14![Avianca logo]()
$382
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:03 am -
1 stop13h 54m
Mon 10/263:13 pm -
1 stop18h 06m
Deal found 9/15![Copa Airlines logo]()
$383
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:05 pm -
1 stop29h 52m
Wed 11/42:13 pm -
1 stop18h 54m
Deal found 9/14![Copa Airlines logo]()
$365
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 10/216:00 am -
1 stop12h 55m
Sat 11/710:55 am -
2 stops9h 55m
Deal found 9/15![American Airlines logo]()
$380
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.
Tue 10/2710:03 am -
1 stop14h 02m
Tue 11/32:13 pm -
1 stop20h 46m
Deal found 9/16![Copa Airlines logo]()
$384
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:05 pm -
1 stop30h 00m
Thu 11/52:13 pm -
1 stop16h 49m
Deal found 9/14![Copa Airlines logo]()
$374
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 10/3011:35 am -
1 stop9h 01m
Wed 11/45:30 pm -
1 stop17h 55m
Deal found 9/16![United Airlines logo]()
$375
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.
Fri 10/3011:35 am -
1 stop9h 01m
Sat 11/77:55 pm -
1 stop15h 30m
Deal found 9/17![United Airlines logo]()
$387
One-way flights from San José to ChicagoSearch for one-way flight options from San José to Chicago. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
Search for one-way flight options from San José to Chicago. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/109:45 am -
1 stop20h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$185
This Volaris 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/24:15 pm -
1 stop18h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$202
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.
Thu 12/172:10 pm -
1 stop10h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Southwest logo]()
$228
This Volaris 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/184:15 pm -
1 stop18h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$245
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.
Wed 12/91:20 pm -
1 stop7h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$246
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.
Fri 11/62:10 pm -
1 stop11h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$247
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/212:05 pm -
1 stop8h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![JetBlue logo]()
$256
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.
Fri 2/192:45 pm -
1 stop9h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$257
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/63:05 pm -
1 stop8h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![JetBlue logo]()
$260
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/134:15 pm -
1 stop18h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Multiple Airlines logo]()
$263
This Volaris 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/44:15 pm -
1 stop18h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$266
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.
Thu 2/181:50 pm -
2 stops18h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$267
Find flight deals from San José to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from San José (SJO) to Chicago (CHI). 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 | $365 (Kiwi.com) |
One-way from | $185 (Super.com) |
Popular in | July |
Cheapest in | January |
Average price | $499 |
Good round-trip deal | $360 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from San José to Chicago 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 San José to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Tue 3/2
4:15 pm-11:13 am
1 stop18h 58m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$202
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Thu 12/10
4:15 pm-11:13 am
1 stop18h 58m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$266
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Sun 12/6
4:15 pm-11:13 am
1 stop18h 58m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$266
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Sun 10/4
4:15 pm-12:09 pm
1 stop18h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$266
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Mon 12/21
3:25 pm-11:10 pm
1 stop7h 45m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$288
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Sun 12/6
1:20 pm-9:00 am
2 stops19h 40m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$298
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Sat 2/13
1:50 pm-10:40 pm
1 stop8h 50m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$320
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Mon 2/22
2:45 pm-10:45 pm
1 stop8h 00m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$330
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Fri 12/11
1:20 pm-12:05 am
2 stops10h 45m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$335
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Thu 1/7
4:15 pm-11:13 am
1 stop18h 58m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$336
Showing 1-10 of 41 resultsSorted by cheapest first
Compare providers for flights from San José to Chicago
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 San José to Chicago in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on San José-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San José-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San José-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San José-Chicago 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 San José-Chicago 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 San José to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from San José with our price prediction graph.
SJO-CHI
SJO-MDW
SJO-ORD
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 San José to Chicago
SJO-CHI
SJO-MDW
SJO-ORD
What is the cheapest month to book a flight from San José to Chicago?
Currently, January is the cheapest month in which you can book a flight from San José to Chicago (average of $385). Flying from San José to Chicago in July is currently the most expensive (average of $640). 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 San José to Chicago?
Airfare is below average for this route at the moment.
San José to Chicago flights typically cost between $405 and $584 in October.The cheapest round-trip price found within the last 5 days was $365 on Copa Airlines (Oct 21-Nov 4).
How often are flights from San José to Chicago delayed?
About 6% of weekly flights between San José and Chicago have experienced delays in the past year, with the average delay time being 231 minutes.
What is the most punctual flight time for San José to Chicago 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?
Tuesday 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 San José to Chicago flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 5% of flights being delayed.
How far ahead should I book a flight from San José to Chicago?
To ensure you get the cheapest price possible for a flight from San José to Chicago, you should look to book at least 89 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 17, 2026.
Read through reviews of airlines operating flights from San José to Chicago, such as Southwest,Copa Airlines, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from San José to Chicago. 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 Chicago?
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Other flights to Chicago
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San José and Chicago flights
Browse other San José and Chicago flight options. Last updated on September 17, 2026.
Other flights from San José
Browse through other flights departing from San José. Flights are based on user searches made on Cheapflights and were last updated on September 17, 2026.
Popular flight searches
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Top 5 airlines flying from San José to Chicago
Discover the top 5 airlines that operate flights from San José to Chicago. 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$189 | Average$448 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$339 | Average$512 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$360 | Average$484 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$375 | Average$636 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$390 | Average$589 | FlexibilityNo cancel fee | On-time63% |