$141+ Cheap flights from Chicago (CHI) to San Jose, CA (SJC)
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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJC
Oct 19 — Oct 261
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to San Jose 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 Jose are usually found in January or October, booked 30 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday
Cheap flight deals from Chicago to San Jose
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Cheapest flights from Chicago to San JoseExplore the most affordable flight options available from Chicago to San Jose. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 19, 2026.
Explore the most affordable flight options available from Chicago to San Jose. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 19, 2026.
This Expedia deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 11/57:20 am -
1 stop8h 45m
Thu 11/122:41 pm -
1 stop12h 32m
Deal found 9/19![Multiple Airlines logo]()
$283
This Priceline deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/202:14 pm -
1 stop7h 39m
Mon 10/269:02 pm -
1 stop6h 14m
Deal found 9/19![Multiple Airlines logo]()
$284
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.
Sat 10/247:10 pm -
Nonstop4h 35m
Sat 10/316:40 am -
Nonstop4h 00m
Deal found 9/16![Southwest logo]()
$287
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.
Thu 10/228:01 pm -
1 stop26h 06m
Mon 10/262:15 pm -
2 stops20h 36m
Deal found 9/16![Frontier logo]()
$288
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:01 pm -
1 stop26h 06m
Mon 10/269:02 pm -
1 stop6h 14m
Deal found 9/17![Frontier logo]()
$289
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:15 pm -
1 stop22h 31m
Mon 11/22:41 pm -
1 stop12h 32m
Deal found 9/17![Frontier logo]()
$291
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/173:49 pm -
1 stop9h 10m
Mon 10/192:15 pm -
1 stop14h 19m
Deal found 9/14![Multiple Airlines logo]()
$292
This Frontier deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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.
Thu 11/265:19 am -
1 stop12h 11m
Thu 12/33:48 pm -
1 stop11h 11m
Deal found 9/18![Frontier logo]()
$294
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/147:40 am -
2 stops31h 40m
Mon 10/192:15 pm -
1 stop14h 19m
Deal found 9/16![Frontier logo]()
$296
This Alaska Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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.
Sat 10/172:21 pm -
1 stop10h 31m
Tue 10/204:48 pm -
1 stop10h 52m
Deal found 9/18![Alaska Airlines logo]()
$297
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1512:26 pm -
2 stops33h 41m
Thu 10/222:15 pm -
1 stop14h 19m
Deal found 9/17![Frontier logo]()
$298
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:30 am -
2 stops15h 42m
Fri 11/69:07 pm -
2 stops22h 03m
Deal found 9/16![Frontier logo]()
$300
Best flights from Chicago to San JoseDiscover carefully curated flight deals from Chicago to San Jose that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 19, 2026.
Discover carefully curated flight deals from Chicago to San Jose that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 19, 2026.
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 10/225:25 am -
1 stop7h 35m
Mon 10/2611:00 pm -
Nonstop4h 00m
Deal found 9/16![Southwest logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/207:55 pm -
Nonstop4h 47m
Mon 10/264:10 pm -
1 stop5h 49m
Deal found 9/19![United Airlines logo]()
$347
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/206:04 am -
1 stop7h 40m
Mon 10/266:20 am -
1 stop8h 27m
Deal found 9/19![Delta logo]()
$357
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:20 am -
1 stop9h 35m
Tue 10/278:02 am -
1 stop8h 18m
Deal found 9/16![Alaska Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/203:30 pm -
1 stop8h 15m
Mon 10/266:00 am -
Nonstop4h 00m
Deal found 9/19![Southwest logo]()
$347
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/2712:49 pm -
1 stop10h 36m
Tue 11/312:57 pm -
1 stop7h 36m
Deal found 9/19![Delta logo]()
$357
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/172:15 pm -
1 stop10h 16m
Wed 12/29:54 am -
1 stop7h 06m
Deal found 9/16![Alaska Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/266:40 am -
1 stop9h 18m
Tue 12/18:56 pm -
2 stops10h 08m
Deal found 9/18![Delta logo]()
$362
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.
Sat 11/146:10 pm -
Nonstop4h 50m
Sat 11/2111:00 pm -
Nonstop4h 00m
Deal found 9/14![Southwest logo]()
$372
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/47:35 am -
1 stop7h 12m
Sat 11/76:00 am -
2 stops8h 26m
Deal found 9/18![Delta logo]()
$362
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 10/167:55 pm -
Nonstop4h 47m
Sun 10/186:30 am -
Nonstop4h 22m
Deal found 9/16![United Airlines logo]()
$457
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 11/183:50 pm -
Nonstop4h 40m
Sun 11/223:00 pm -
1 stop7h 15m
Deal found 9/16![Southwest logo]()
$382
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/305:46 pm -
2 stops16h 31m
Fri 11/67:37 am -
1 stop9h 22m
Deal found 9/15![Alaska Airlines logo]()
$433
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 11/248:08 pm -
Nonstop4h 51m
Tue 12/12:15 pm -
Nonstop4h 19m
Deal found 9/14![United Airlines logo]()
$457
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:20 pm -
2 stops7h 10m
Tue 11/108:10 am -
2 stops7h 10m
Deal found 9/17![Southwest logo]()
$402
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:20 am -
1 stop9h 35m
Thu 10/225:15 pm -
2 stops10h 25m
Deal found 9/14![Alaska Airlines logo]()
$456
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/109:05 am -
2 stops8h 05m
Tue 10/137:00 pm -
1 stop7h 30m
Deal found 9/17![Southwest logo]()
$429
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 10/206:20 am -
2 stops9h 37m
Mon 10/262:37 pm -
1 stop6h 57m
Deal found 9/16![Delta logo]()
$477
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:00 am -
2 stops17h 52m
Mon 10/1911:12 am -
2 stops16h 28m
Deal found 9/14![Alaska Airlines logo]()
$487
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 11/196:05 am -
1 stop6h 20m
Mon 11/3011:00 pm -
Nonstop4h 00m
Deal found 9/16![Southwest logo]()
$433
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/76:20 am -
2 stops11h 31m
Tue 10/1311:30 am -
1 stop10h 04m
Deal found 9/19![Delta logo]()
$497
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.
Fri 10/3011:20 am -
1 stop7h 05m
Sun 11/17:20 pm -
1 stop7h 05m
Deal found 9/15![Southwest logo]()
$434
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 10/141:05 pm -
2 stops7h 55m
Mon 10/198:25 pm -
1 stop7h 15m
Deal found 9/16![Southwest logo]()
$438
Last-minute flights from Chicago to San JoseDiscover last-minute flight deals from Chicago to San Jose. Data last updated September 19, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San Jose. Data last updated September 19, 2026 and is based on user searches.
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/147:40 am -
2 stops31h 40m
Mon 10/192:15 pm -
1 stop14h 19m
Deal found 9/16![Frontier logo]()
$296
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:01 pm -
1 stop26h 06m
Mon 10/269:02 pm -
1 stop6h 14m
Deal found 9/17![Frontier logo]()
$289
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1512:26 pm -
2 stops33h 41m
Thu 10/222:15 pm -
1 stop14h 19m
Deal found 9/17![Frontier logo]()
$298
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:20 am -
1 stop9h 35m
Mon 10/192:15 pm -
1 stop14h 19m
Deal found 9/14![Multiple Airlines logo]()
$292
This Alaska Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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.
Sat 10/172:21 pm -
1 stop10h 31m
Tue 10/204:48 pm -
1 stop10h 52m
Deal found 9/18![Alaska Airlines logo]()
$297
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/183:30 pm -
1 stop23h 50m
Thu 10/229:02 pm -
1 stop6h 14m
Deal found 9/16![Frontier logo]()
$304
This Priceline deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/202:14 pm -
1 stop7h 39m
Mon 10/269:02 pm -
1 stop6h 14m
Deal found 9/19![Multiple Airlines logo]()
$284
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:00 am -
1 stop8h 18m
Fri 10/232:15 pm -
1 stop14h 19m
Deal found 9/16![Multiple Airlines logo]()
$302
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.
Thu 10/228:01 pm -
1 stop26h 06m
Mon 10/262:15 pm -
2 stops20h 36m
Deal found 9/16![Frontier logo]()
$288
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.
Sat 10/247:10 pm -
Nonstop4h 35m
Sat 10/316:40 am -
Nonstop4h 00m
Deal found 9/16![Southwest logo]()
$287
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.
Mon 10/266:30 am -
2 stops15h 37m
Mon 11/22:41 pm -
1 stop12h 32m
Deal found 9/15![Frontier logo]()
$294
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:15 pm -
1 stop22h 31m
Mon 11/22:41 pm -
1 stop12h 32m
Deal found 9/17![Frontier logo]()
$291
One-way flights from Chicago to San JoseSearch for one-way flight options from Chicago to San Jose. Find affordable one-way fares based on user searches. Data last updated September 19, 2026.
Search for one-way flight options from Chicago to San Jose. Find affordable one-way fares based on user searches. Data last updated September 19, 2026.
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 10/143:30 pm -
2 stops30h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$141
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 10/288:40 pm -
Nonstop4h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$144
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 11/186:16 am -
2 stops39h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$146
This Alaska Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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.
Sat 10/177:20 am -
1 stop9h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Alaska Airlines logo]()
$149
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.
Tue 10/135:00 am -
1 stop9h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$153
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:27 pm -
2 stops33h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$154
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:15 am -
2 stops38h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$154
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.
Sat 11/147:25 am -
2 stops38h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$158
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/57:30 am -
1 stop12h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$159
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.
Thu 11/126:16 am -
2 stops39h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$160
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.
Thu 10/228:01 pm -
1 stop26h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$160
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.
Thu 10/151:12 pm -
2 stops32h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$161
Find flight deals from Chicago to San Jose
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to San Jose (SJC). 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 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $283 (Expedia) |
One-way from | $141 (Kiwi.com) |
Popular in | February |
Cheapest in | January |
Average price | $497 |
Good round-trip deal | $357 or less |
Good one-way deal | $178 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to San Jose 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 19, 2026.
Use the filters below to find and compare flights from Chicago to San Jose that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoSan Jose
MDW Chicago Midway - SJC San Jose
MDWSJC
Chicago Midway
Tue 12/15
3:50 pm-6:30 pm
Nonstop4h 40m
San Jose
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$144
ChicagoSan Jose
ORD Chicago O'Hare Intl - SJC San Jose
ORDSJC
Chicago O'Hare Intl
Wed 11/11
2:15 pm-10:31 pm
1 stop10h 16m
San Jose
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$149
ChicagoSan Jose
MDW Chicago Midway - SJC San Jose
MDWSJC
Chicago Midway
Sat 11/14
12:55 pm-8:05 pm
2 stops9h 10m
San Jose
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$159
ChicagoSan Jose
MDW Chicago Midway - SJC San Jose
MDWSJC
Chicago Midway
Tue 11/17
10:10 am-12:55 pm
Nonstop4h 45m
San Jose
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$169
ChicagoSan Jose
MDW Chicago Midway - SJC San Jose
MDWSJC
Chicago Midway
Wed 11/11
6:00 am-11:50 am
1 stop7h 50m
San Jose
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
ChicagoSan Jose
MDW Chicago Midway - SJC San Jose
MDWSJC
Chicago Midway
Tue 12/15
1:02 pm-10:13 pm
1 stop11h 11m
San Jose
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
ChicagoSan Jose
ORD Chicago O'Hare Intl - SJC San Jose
ORDSJC
Chicago O'Hare Intl
Wed 10/21
7:20 am-2:55 pm
1 stop9h 35m
San Jose
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
ChicagoSan Jose
ORD Chicago O'Hare Intl - SJC San Jose
ORDSJC
Chicago O'Hare Intl
Tue 12/1
7:27 am-1:54 pm
1 stop8h 27m
San Jose
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
ChicagoSan Jose
ORD Chicago O'Hare Intl - SJC San Jose
ORDSJC
Chicago O'Hare Intl
Tue 11/3
2:07 pm-7:46 pm
1 stop7h 39m
San Jose
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
ChicagoSan Jose
MDW Chicago Midway - SJC San Jose
MDWSJC
Chicago Midway
Wed 12/16
12:39 pm-8:16 pm
2 stops9h 37m
San Jose
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$184
Showing 1-10 of 47 resultsSorted by cheapest first
Compare providers for flights from Chicago to San Jose
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 Jose in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-San Jose, California flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-San Jose, California flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-San Jose, California flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-San Jose, California 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 Jose, California 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 Jose
Have a flexible travel schedule? Discover the best time to fly to San Jose from Chicago with our price prediction graph.
CHI-SJC
MDW-SJC
ORD-SJC
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 Jose
CHI-SJC
MDW-SJC
ORD-SJC
What is the cheapest month to book a flight from Chicago to San Jose, California?
Currently, July is the cheapest month in which you can book a flight from Chicago to San Jose, California (average of $412). Flying from Chicago to San Jose, California in February is currently the most expensive (average of $566). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to SJC?
Find hourly flight availability from Chicago to San Jose. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 19, 2026.
One of the essential ways to save on airfare from Chicago to San Jose, California is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight at noon could potentially save you up to 19% on airfare.
How much does it cost to fly round-trip from Chicago to San Jose, California?
Airfare is below average for this route at the moment.
Chicago to San Jose, California flights typically cost between $342 and $600 in November.The cheapest round-trip price found within the last 5 days was $283 on Multiple Airlines (Nov 5-Nov 12).
How far ahead should I book a flight from Chicago to San Jose, California?
Booking 70 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to San Jose, California. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
The best insider tips for Chicago to San Jose 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 Chicago to San Jose trip
Our travel experts
Reviews of airlines servicing San Jose
Get insights into the airlines that provide service to San Jose. 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 Jose. Reviews last updated September 19, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, andDelta from Chicago to San Jose by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to San Jose. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Complete your trip
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Chicago and San Jose flights
Browse other Chicago and San Jose flight options. Last updated on September 19, 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 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to San Jose
Explore flights to San Jose departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 19, 2026.
Top 5 airlines flying from Chicago to San Jose
Discover the top 5 airlines that operate flights from Chicago to San Jose. 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 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$136 | Average$384 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$232 | Average$366 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$256 | Average$526 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$298 | Average$457 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$298 | Average$478 | FlexibilityNo cancel fee | On-time69% |