$166+ Cheap flights from San Jose, CA (SJC) to Chicago (CHI)
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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — CHI
Sep 16 — Sep 231
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from San Jose 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 Jose to Chicago are usually found in February or April, booked 79 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday
Cheap flight deals from San Jose to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from San Jose to ChicagoExplore the most affordable flight options available from San Jose to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 17, 2026.
Explore the most affordable flight options available from San Jose to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 17, 2026.
This Delta deal was found by Cheapflights users on 8/12. 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.
Tue 9/112:40 pm -
1 stop7h 56m
Sat 9/59:59 am -
1 stop9h 35m
Deal found 8/12![Delta logo]()
$314
This Delta deal was found by Cheapflights users on 8/12. 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.
Mon 8/312:45 pm -
1 stop6h 44m
Sun 9/612:54 pm -
1 stop9h 19m
Deal found 8/12![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 8/16. 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 9/2511:00 pm -
Nonstop4h 00m
Mon 9/288:50 pm -
Nonstop4h 35m
Deal found 8/16![Southwest logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Mon 9/211:38 pm -
1 stop14h 00m
Wed 9/231:21 pm -
2 stops32h 32m
Deal found 8/16![Frontier logo]()
$315
This Southwest deal was found by Cheapflights users on 8/13. 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 10/216:25 am -
2 stops7h 40m
Thu 10/226:05 am -
1 stop7h 40m
Deal found 8/13![Southwest logo]()
$316
This Delta deal was found by Cheapflights users on 8/15. 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 11/22:59 pm -
2 stops16h 28m
Mon 11/2312:58 pm -
1 stop7h 39m
Deal found 8/15![Delta logo]()
$316
This Alaska Airlines deal was found by Cheapflights users on 8/12. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/410:12 am -
1 stop7h 09m
Sun 9/66:05 am -
1 stop6h 54m
Deal found 8/12![Alaska Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 8/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2311:00 pm -
Nonstop4h 00m
Thu 11/2610:15 am -
2 stops7h 55m
Deal found 8/17![Southwest logo]()
$318
This Southwest deal was found by Cheapflights users on 8/15. 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 9/3011:00 pm -
Nonstop4h 00m
Sat 10/37:10 pm -
Nonstop4h 35m
Deal found 8/15![Southwest logo]()
$319
This Expedia deal was found by Cheapflights users on 8/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:02 pm -
1 stop28h 00m
Wed 9/97:20 am -
1 stop8h 10m
Deal found 8/14![Multiple Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 8/13. 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.
Tue 9/111:00 pm -
Nonstop4h 00m
Wed 9/28:30 pm -
Nonstop4h 30m
Deal found 8/13![Southwest logo]()
$320
This Delta deal was found by Cheapflights users on 8/12. 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 9/3011:32 am -
1 stop10h 25m
Fri 10/212:50 pm -
1 stop9h 20m
Deal found 8/12![Delta logo]()
$320
Best flights from San Jose to ChicagoDiscover carefully curated flight deals from San Jose to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 17, 2026.
Discover carefully curated flight deals from San Jose to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 17, 2026.
This United Airlines deal was found by Cheapflights users on 8/14. 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.
Mon 9/142:10 pm -
Nonstop4h 25m
Mon 9/218:03 pm -
Nonstop4h 47m
Deal found 8/14![United Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 8/16. 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 10/238:00 am -
2 stops7h 25m
Mon 10/267:15 pm -
1 stop6h 40m
Deal found 8/16![Southwest logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 10/152:15 pm -
2 stops19h 12m
Sun 10/189:33 pm -
1 stop17h 47m
Deal found 8/15![Multiple Airlines logo]()
$324
This Alaska Airlines deal was found by Cheapflights users on 8/16. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3010:12 am -
1 stop7h 09m
Wed 10/79:00 am -
2 stops15h 52m
Deal found 8/16![Alaska Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 8/14. 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 10/12:56 pm -
1 stop6h 35m
Sun 10/47:00 am -
1 stop9h 01m
Deal found 8/14![Delta logo]()
$347
This Southwest deal was found by Cheapflights users on 8/16. 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 11/1811:55 am -
2 stops7h 30m
Sun 11/229:15 pm -
Nonstop4h 40m
Deal found 8/16![Southwest logo]()
$342
This Alaska Airlines deal was found by Cheapflights users on 8/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2910:12 am -
1 stop7h 09m
Tue 10/69:00 am -
2 stops15h 52m
Deal found 8/15![Alaska Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 10/82:15 pm -
2 stops19h 12m
Sun 10/119:33 pm -
1 stop17h 47m
Deal found 8/15![Multiple Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 8/12. 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.
Thu 9/1011:32 am -
1 stop10h 25m
Sun 9/137:00 am -
1 stop9h 01m
Deal found 8/12![Delta logo]()
$371
This Southwest deal was found by Cheapflights users on 8/13. 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 12/166:00 am -
Nonstop4h 10m
Mon 12/213:15 pm -
1 stop7h 00m
Deal found 8/13![Southwest logo]()
$350
This Delta deal was found by Cheapflights users on 8/12. 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.
Thu 10/86:05 am -
1 stop8h 35m
Sat 10/105:00 pm -
1 stop7h 08m
Deal found 8/12![Delta logo]()
$379
This United Airlines deal was found by Cheapflights users on 8/13. 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.
Wed 9/232:10 pm -
Nonstop4h 25m
Thu 9/249:14 am -
Nonstop4h 47m
Deal found 8/13![United Airlines logo]()
$417
This Southwest deal was found by Cheapflights users on 8/13. 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.
Thu 11/510:00 am -
2 stops8h 05m
Mon 11/95:20 pm -
2 stops7h 10m
Deal found 8/13![Southwest logo]()
$366
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Thu 8/271:02 pm -
2 stops20h 21m
Sun 8/309:35 pm -
1 stop17h 47m
Deal found 8/13![Multiple Airlines logo]()
$415
This Alaska Airlines deal was found by Cheapflights users on 8/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:44 pm -
1 stop8h 15m
Tue 9/87:20 am -
1 stop28h 03m
Deal found 8/15![Alaska Airlines logo]()
$425
This United Airlines deal was found by Cheapflights users on 8/13. 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.
Thu 9/172:10 pm -
Nonstop4h 25m
Tue 9/226:00 am -
1 stop9h 08m
Deal found 8/13![United Airlines logo]()
$427
This Alaska Airlines deal was found by Cheapflights users on 8/12. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:06 pm -
1 stop18h 16m
Sat 9/196:00 am -
2 stops14h 04m
Deal found 8/12![Alaska Airlines logo]()
$427
This United Airlines deal was found by Cheapflights users on 8/13. 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 10/91:00 pm -
1 stop8h 59m
Sat 10/109:14 am -
Nonstop4h 47m
Deal found 8/13![United Airlines logo]()
$427
This Southwest deal was found by Cheapflights users on 8/15. 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 11/2011:50 am -
Nonstop4h 00m
Thu 11/2610:15 am -
Nonstop4h 40m
Deal found 8/15![Southwest logo]()
$391
This Delta deal was found by Cheapflights users on 8/14. 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.
Fri 9/412:40 pm -
1 stop7h 56m
Sat 9/59:59 am -
1 stop9h 35m
Deal found 8/14![Delta logo]()
$433
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 10/149:03 pm -
2 stops21h 10m
Sun 10/189:33 pm -
1 stop17h 47m
Deal found 8/14![Multiple Airlines logo]()
$470
This Alaska Airlines deal was found by Cheapflights users on 8/13. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:29 am -
2 stops13h 30m
Sun 10/47:49 pm -
1 stop16h 05m
Deal found 8/13![Alaska Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 8/13. 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 10/306:05 am -
1 stop8h 42m
Mon 11/212:27 pm -
1 stop7h 26m
Deal found 8/13![Delta logo]()
$448
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Thu 8/271:02 pm -
2 stops20h 21m
Thu 9/39:29 pm -
1 stop17h 53m
Deal found 8/13![Multiple Airlines logo]()
$489
This Delta deal was found by Cheapflights users on 8/16. 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.
Fri 9/2510:50 pm -
1 stop9h 46m
Thu 10/11:00 pm -
1 stop10h 22m
Deal found 8/16![Delta logo]()
$448
This Southwest deal was found by Cheapflights users on 8/14. 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 9/111:00 pm -
Nonstop4h 00m
Fri 9/48:50 pm -
Nonstop4h 35m
Deal found 8/14![Southwest logo]()
$468
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:50 am -
1 stop6h 50m
Mon 8/318:50 pm -
Nonstop4h 30m
Deal found 8/12![Southwest logo]()
$470
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:55 pm -
1 stop7h 35m
Mon 8/318:50 pm -
Nonstop4h 30m
Deal found 8/12![Southwest logo]()
$470
This Kiwi.com deal was found by Cheapflights users on 8/15. 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.
Sat 12/2611:58 am -
1 stop21h 39m
Tue 12/299:02 pm -
1 stop16h 01m
Deal found 8/15![Multiple Airlines logo]()
$733
Last-minute flights from San Jose to ChicagoDiscover last-minute flight deals from San Jose to Chicago. Data last updated August 17, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Chicago. Data last updated August 17, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/12. 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.
Mon 8/312:45 pm -
1 stop6h 44m
Sun 9/612:54 pm -
1 stop9h 19m
Deal found 8/12![Delta logo]()
$314
This Delta deal was found by Cheapflights users on 8/12. 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.
Tue 9/112:40 pm -
1 stop7h 56m
Sat 9/59:59 am -
1 stop9h 35m
Deal found 8/12![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 8/13. 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.
Tue 9/111:00 pm -
Nonstop4h 00m
Wed 9/28:30 pm -
Nonstop4h 30m
Deal found 8/13![Southwest logo]()
$320
This Expedia deal was found by Cheapflights users on 8/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:02 pm -
1 stop28h 00m
Wed 9/97:20 am -
1 stop8h 10m
Deal found 8/14![Multiple Airlines logo]()
$319
This CheapOair deal was found by Cheapflights users on 8/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:02 pm -
1 stop28h 00m
Wed 9/91:21 pm -
1 stop25h 22m
Deal found 8/15![Frontier logo]()
$321
This Alaska Airlines deal was found by Cheapflights users on 8/12. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/410:12 am -
1 stop7h 09m
Sun 9/66:05 am -
1 stop6h 54m
Deal found 8/12![Alaska Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 8/16. 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 9/187:35 pm -
1 stop7h 30m
Mon 9/216:15 am -
1 stop7h 40m
Deal found 8/16![Southwest logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Mon 9/211:38 pm -
1 stop14h 00m
Wed 9/231:21 pm -
2 stops32h 32m
Deal found 8/16![Frontier logo]()
$315
This Southwest deal was found by Cheapflights users on 8/16. 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 9/2511:00 pm -
Nonstop4h 00m
Mon 9/288:50 pm -
Nonstop4h 35m
Deal found 8/16![Southwest logo]()
$315
This Southwest deal was found by Cheapflights users on 8/13. 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 9/257:50 pm -
1 stop7h 35m
Thu 10/111:55 am -
1 stop7h 10m
Deal found 8/13![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 8/15. 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 9/3011:00 pm -
Nonstop4h 00m
Sat 10/37:10 pm -
Nonstop4h 35m
Deal found 8/15![Southwest logo]()
$319
This Delta deal was found by Cheapflights users on 8/12. 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 9/3011:32 am -
1 stop10h 25m
Fri 10/212:50 pm -
1 stop9h 20m
Deal found 8/12![Delta logo]()
$320
One-way flights from San Jose to ChicagoSearch for one-way flight options from San Jose to Chicago. Find affordable one-way fares based on user searches. Data last updated August 17, 2026.
Search for one-way flight options from San Jose to Chicago. Find affordable one-way fares based on user searches. Data last updated August 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 10/99:16 pm -
2 stops25h 08m
Deal found 8/13![Frontier logo]()
$166
This United Airlines deal was found by Cheapflights users on 8/17. 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 9/92:10 pm -
Nonstop4h 25m
Deal found 8/17![United Airlines logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:16 pm -
2 stops24h 27m
Deal found 8/17![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/119:03 pm -
2 stops25h 20m
Deal found 8/17![Frontier logo]()
$170
This Frontier deal was found by Cheapflights users on 8/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/68:14 pm -
1 stop7h 45m
Deal found 8/14![Frontier logo]()
$171
This Super.com deal was found by Cheapflights users on 8/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:14 pm -
1 stop8h 03m
Deal found 8/13![Frontier logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Mon 9/141:38 pm -
2 stops26h 08m
Deal found 8/16![Frontier logo]()
$174
This Southwest deal was found by Cheapflights users on 8/15. 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.
Sat 10/176:30 am -
2 stops9h 30m
Deal found 8/15![Southwest logo]()
$175
This Frontier deal was found by Cheapflights users on 8/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/318:14 pm -
1 stop8h 03m
Deal found 8/17![Frontier logo]()
$175
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3111:00 pm -
Nonstop4h 00m
Deal found 8/12![Southwest logo]()
$177
This Super.com deal was found by Cheapflights users on 8/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:02 pm -
1 stop28h 00m
Deal found 8/15![Frontier logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 8/15. 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.
Fri 9/119:03 pm -
2 stops12h 56m
Deal found 8/15![Frontier logo]()
$178
Find flight deals from San Jose to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from San Jose (SJC) 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 August 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $314 (Delta) |
One-way from | $166 (Kiwi.com) |
Popular in | December |
Cheapest in | February |
Average price | $425 |
Good round-trip deal | $389 or less |
Good one-way deal | $178 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from San Jose 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 2,558,603 searches. Data last updated August 17, 2026.
Use the filters below to find and compare flights from San Jose to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Mon 9/14
2:10 pm-8:35 pm
Nonstop4h 25m
Chicago O'Hare Intl
Mon 9/21
8:03 pm-10:50 pm
Nonstop4h 47m
$319
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Fri 10/23
8:00 am-5:25 pm
2 stops7h 25m
Chicago Midway
Mon 10/26
7:15 pm-11:55 pm
1 stop6h 40m
$324
San JoseChicago
SJC San Jose - RFD Chicago Greater Rockford
SJCRFD
San Jose
Thu 10/15
2:15 pm-11:27 am
2 stops19h 12m
Chicago Greater Rockford
Sun 10/18
9:33 pm-1:20 pm
1 stop17h 47m
$324
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Wed 11/18
11:55 am-9:25 pm
2 stops7h 30m
Chicago Midway
Sun 11/22
9:15 pm-11:55 pm
Nonstop4h 40m
$342
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Wed 9/30
10:12 am-7:21 pm
1 stop7h 09m
Chicago O'Hare Intl
Wed 10/7
9:00 am-10:52 pm
2 stops15h 52m
$346
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Tue 9/29
10:12 am-7:21 pm
1 stop7h 09m
Chicago O'Hare Intl
Tue 10/6
9:00 am-10:52 pm
2 stops15h 52m
$346
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Thu 10/1
2:56 pm-11:31 pm
1 stop6h 35m
Chicago O'Hare Intl
Sun 10/4
7:00 am-2:01 pm
1 stop9h 01m
$347
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Wed 12/16
6:00 am-12:10 pm
Nonstop4h 10m
Chicago Midway
Mon 12/21
3:15 pm-8:15 pm
1 stop7h 00m
$350
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Thu 11/5
10:00 am-8:05 pm
2 stops8h 05m
Chicago Midway
Mon 11/9
5:20 pm-10:30 pm
2 stops7h 10m
$366
San JoseChicago
SJC San Jose - RFD Chicago Greater Rockford
SJCRFD
San Jose
Thu 10/8
2:15 pm-11:27 am
2 stops19h 12m
Chicago Greater Rockford
Sun 10/11
9:33 pm-1:20 pm
1 stop17h 47m
$369
Showing 1-10 of 59 resultsSorted by cheapest first
Compare providers for flights from San Jose 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 Jose to Chicago in August.
| 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 Jose, California-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Jose, California-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Jose, California-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San Jose, California-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 Jose, California-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 Jose to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from San Jose with our price prediction graph.
SJC-CHI
SJC-ORD
SJC-MDW
SJC-RFD
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 Jose to Chicago
SJC-CHI
SJC-ORD
SJC-MDW
SJC-RFD
What is the cheapest month to book a flight from San Jose, California to Chicago?
Currently, April is the cheapest month in which you can book a flight from San Jose, California to Chicago (average of $405). Flying from San Jose, California to Chicago in June is currently the most expensive (average of $577). 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 SJC to CHI?
Find hourly flight availability from San Jose to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 17, 2026.
A simple way to save on the total cost of your ticket is to fly from San Jose, California to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 22% on your trip compared to booking a flight at noon.
Weekly flight availability from San Jose, California to Chicago
Explore weekly flight availability from San Jose to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 17, 2026.
The most flights from SJC to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).
How much does it cost to fly round-trip from San Jose, California to Chicago?
Airfare is below average for this route at the moment.
San Jose, California to Chicago flights typically cost between $346 and $596 in September.The cheapest round-trip price found within the last 5 days was $314 on Delta (Sep 1-Sep 5).
How far ahead should I book a flight from San Jose, California to Chicago?
The best time to book flights from San Jose, California to Chicago is 66 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
The best insider tips for San Jose to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your San Jose to Chicago trip
Our travel experts
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 August 17, 2026.
Peruse reviews from past customers who have flown with Southwest,Alaska Airlines, andDelta from San Jose to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
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 Jose 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?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from San Jose
Popular flights
Alternative routes for San Jose to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 17, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from San Jose to Chicago by cabin class
Find flights from San Jose to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
San Jose and Chicago flights
Browse other San Jose and Chicago flight options. Last updated on August 17, 2026.
Other flights from San Jose
Browse through other flights departing from San Jose. Flights are based on user searches made on Cheapflights and were last updated on August 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from San Jose to Chicago
Discover the top 6 airlines that operate flights from San Jose 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 2,558,603 searches. Data last updated August 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$131 | Average$490 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$200 | Average$427 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$236 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$256 | Average$344 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$270 | Average$510 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$294 | Average$563 | FlexibilityNo cancel fee | On-time69% |