$118+ Cheap flights from Chicago (CHI) to San Jose, CA (SJC)
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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJC
Aug 18 — Aug 251
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to San 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
Cheapest
Best
Last-minute
One-way
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 July 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 July 19, 2026.
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:00 pm
MDW
- SJC
1 stop6h 15m
Southwest
Tue 8/256:45 am
SJC
- MDW
2 stops7h 15m
Southwest
Deal found 7/15![Southwest logo]()
$262
This United Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Thu 8/272:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Deal found 7/16![United Airlines logo]()
$262
This Frontier deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:29 am
ORD
- SJC
1 stop7h 48m
Frontier
Fri 8/218:14 pm
SJC
- ORD
1 stop8h 03m
Frontier
Deal found 7/16![Frontier logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:41 pm
ORD
- SJC
2 stops30h 38m
Frontier
Mon 8/318:14 pm
SJC
- ORD
1 stop8h 03m
Frontier
Deal found 7/14![Frontier logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:50 am
ORD
- SJC
1 stop8h 39m
Frontier
Mon 9/149:03 pm
SJC
- ORD
2 stops22h 32m
Frontier
Deal found 7/14![Frontier logo]()
$270
This United Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Wed 8/2612:51 pm
SJC
- ORD
1 stop7h 55m
United Airlines
Deal found 7/16![United Airlines logo]()
$272
This Expedia deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:01 am
ORD
- SJC
1 stop9h 44m
Multiple Airlines
Sun 8/308:14 pm
SJC
- ORD
1 stop7h 45m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$273
This CheapOair deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:20 pm
ORD
- SJC
1 stop23h 59m
Frontier
Sun 8/231:02 pm
SJC
- ORD
1 stop28h 00m
Frontier
Deal found 7/14![Frontier logo]()
$274
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:50 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Wed 8/2611:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Deal found 7/14![Southwest logo]()
$277
This Alaska Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:00 am
ORD
- SJC
1 stop9h 18m
Alaska Airlines
Wed 10/78:54 am
SJC
- ORD
1 stop7h 59m
Alaska Airlines
Deal found 7/14![Alaska Airlines logo]()
$277
This United Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:45 pm
ORD
- SJC
1 stop6h 46m
United Airlines
Mon 8/242:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Deal found 7/15![United Airlines logo]()
$278
This Frontier deal was found by Cheapflights users on 7/18. 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.
Sat 8/157:29 am
ORD
- SJC
1 stop7h 48m
Frontier
Sun 8/168:23 pm
SJC
- ORD
1 stop7h 54m
Frontier
Deal found 7/18![Frontier logo]()
$284
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 July 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 July 19, 2026.
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/281:05 pm
MDW
- SJC
2 stops7h 55m
Southwest
Wed 11/49:45 am
SJC
- MDW
2 stops8h 10m
Southwest
Deal found 7/14![Southwest logo]()
$267
This United Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:45 pm
ORD
- SJC
1 stop6h 46m
United Airlines
Mon 8/242:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Deal found 7/15![United Airlines logo]()
$278
This Alaska Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:17 pm
ORD
- SJC
1 stop15h 06m
Alaska Airlines
Sun 10/45:18 pm
SJC
- ORD
1 stop18h 07m
Alaska Airlines
Deal found 7/16![Alaska Airlines logo]()
$302
This Delta deal was found by Cheapflights users on 7/18. 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.
Tue 10/201:00 pm
MDW
- SJC
1 stop10h 25m
Delta
Mon 10/2610:40 pm
SJC
- MDW
1 stop9h 12m
Delta
Deal found 7/18![Delta logo]()
$379
This KAYAK deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:00 am
ORD
- SJC
1 stop8h 33m
American Airlines
Thu 7/232:23 pm
SJC
- ORD
1 stop7h 16m
American Airlines
Deal found 7/14![American Airlines logo]()
$547
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:50 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Wed 8/2611:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Deal found 7/14![Southwest logo]()
$277
This Alaska Airlines deal was found by Cheapflights users on 7/18. 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.
Tue 10/67:20 am
ORD
- SJC
1 stop9h 35m
Alaska Airlines
Wed 10/78:54 am
SJC
- ORD
1 stop7h 59m
Alaska Airlines
Deal found 7/18![Alaska Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/292:15 pm
MDW
- SJC
2 stops9h 05m
Southwest
Sat 9/510:45 am
SJC
- MDW
1 stop7h 30m
Southwest
Deal found 7/15![Southwest logo]()
$302
This United Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:56 pm
ORD
- SJC
1 stop6h 58m
United Airlines
Sat 9/196:30 am
SJC
- ORD
Nonstop4h 25m
United Airlines
Deal found 7/16![United Airlines logo]()
$347
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/221:45 pm
MDW
- SJC
2 stops7h 50m
Southwest
Mon 8/247:55 am
SJC
- MDW
2 stops7h 15m
Southwest
Deal found 7/16![Southwest logo]()
$307
This United Airlines deal was found by Cheapflights users on 7/17. 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 9/22:42 pm
ORD
- SJC
1 stop8h 15m
United Airlines
Mon 9/76:20 am
SJC
- ORD
Nonstop4h 25m
United Airlines
Deal found 7/17![United Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 7/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:00 pm
MDW
- SJC
1 stop10h 25m
Delta
Sat 10/1712:57 pm
SJC
- MDW
1 stop7h 28m
Delta
Deal found 7/17![Delta logo]()
$419
This Alaska Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/42:18 pm
ORD
- SJC
1 stop6h 51m
Alaska Airlines
Mon 9/77:29 am
SJC
- ORD
1 stop14h 30m
Alaska Airlines
Deal found 7/15![Alaska Airlines logo]()
$387
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/19:15 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Sun 10/48:25 am
SJC
- MDW
2 stops7h 35m
Southwest
Deal found 7/16![Southwest logo]()
$337
This United Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/139:00 am
ORD
- SJC
Nonstop4h 46m
United Airlines
Thu 8/2012:51 pm
SJC
- ORD
1 stop9h 08m
United Airlines
Deal found 7/16![United Airlines logo]()
$397
This Southwest deal was found by Cheapflights users on 7/17. 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.
Wed 9/22:05 pm
MDW
- SJC
2 stops8h 15m
Southwest
Mon 9/711:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Deal found 7/17![Southwest logo]()
$370
This United Airlines deal was found by Cheapflights users on 7/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/69:14 am
ORD
- SJC
Nonstop4h 47m
United Airlines
Wed 10/78:45 am
SJC
- ORD
1 stop8h 44m
United Airlines
Deal found 7/18![United Airlines logo]()
$469
This Southwest deal was found by Cheapflights users on 7/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/99:50 am
MDW
- SJC
Nonstop4h 35m
Southwest
Sat 10/109:50 am
SJC
- MDW
1 stop6h 55m
Southwest
Deal found 7/18![Southwest logo]()
$393
This United Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/44:26 pm
ORD
- SJC
1 stop6h 31m
United Airlines
Mon 9/76:20 am
SJC
- ORD
Nonstop4h 25m
United Airlines
Deal found 7/15![United Airlines logo]()
$472
This United Airlines deal was found by Cheapflights users on 7/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/99:14 am
ORD
- SJC
Nonstop4h 47m
United Airlines
Sat 10/106:30 am
SJC
- ORD
Nonstop4h 22m
United Airlines
Deal found 7/18![United Airlines logo]()
$499
This United Airlines deal was found by Cheapflights users on 7/19. 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.
Wed 8/128:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Sun 8/166:20 am
SJC
- ORD
Nonstop4h 25m
United Airlines
Deal found 7/19![United Airlines logo]()
$503
Last-minute flights from Chicago to San JoseDiscover last-minute flight deals from Chicago to San Jose. Data last updated July 19, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San Jose. Data last updated July 19, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Wed 8/1910:12 am
SJC
- ORD
1 stop7h 09m
Alaska Airlines
Deal found 7/14![Alaska Airlines logo]()
$288
This Frontier deal was found by Cheapflights users on 7/18. 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.
Sat 8/157:29 am
ORD
- SJC
1 stop7h 48m
Frontier
Sun 8/168:23 pm
SJC
- ORD
1 stop7h 54m
Frontier
Deal found 7/18![Frontier logo]()
$284
This Frontier deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:29 am
ORD
- SJC
1 stop7h 48m
Frontier
Fri 8/218:14 pm
SJC
- ORD
1 stop8h 03m
Frontier
Deal found 7/16![Frontier logo]()
$264
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:00 pm
MDW
- SJC
1 stop6h 15m
Southwest
Tue 8/256:45 am
SJC
- MDW
2 stops7h 15m
Southwest
Deal found 7/15![Southwest logo]()
$262
This CheapOair deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:20 pm
ORD
- SJC
1 stop23h 59m
Frontier
Sun 8/231:02 pm
SJC
- ORD
1 stop28h 00m
Frontier
Deal found 7/14![Frontier logo]()
$274
This United Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:45 pm
ORD
- SJC
1 stop6h 46m
United Airlines
Mon 8/242:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Deal found 7/15![United Airlines logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/238:11 pm
ORD
- SJC
1 stop19h 11m
Frontier
Thu 8/278:14 pm
SJC
- ORD
1 stop7h 45m
Frontier
Deal found 7/14![Frontier logo]()
$287
This United Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Thu 8/272:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Deal found 7/16![United Airlines logo]()
$262
This United Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Wed 8/2612:51 pm
SJC
- ORD
1 stop7h 55m
United Airlines
Deal found 7/14![United Airlines logo]()
$272
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:50 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Wed 8/2611:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Deal found 7/14![Southwest logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:41 pm
ORD
- SJC
2 stops30h 38m
Frontier
Mon 8/318:14 pm
SJC
- ORD
1 stop8h 03m
Frontier
Deal found 7/14![Frontier logo]()
$268
This Expedia deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:01 am
ORD
- SJC
1 stop9h 44m
Multiple Airlines
Sun 8/308:14 pm
SJC
- ORD
1 stop7h 45m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$273
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 July 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 July 19, 2026.
This Super.com deal was found by Cheapflights users on 7/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/157:29 am
ORD
- SJC
1 stop7h 48m
Frontier
Deal found 7/17![Frontier logo]()
$118
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:50 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 7/14![Southwest logo]()
$119
This United Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 7/14![United Airlines logo]()
$119
This Frontier deal was found by Cheapflights users on 7/17. 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.
Thu 10/16:50 am
ORD
- SJC
1 stop8h 39m
Frontier
Deal found 7/17![Frontier logo]()
$121
This Super.com deal was found by Cheapflights users on 7/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/199:20 pm
ORD
- SJC
1 stop23h 59m
Frontier
Deal found 7/17![Frontier logo]()
$122
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:15 am
MDW
- SJC
1 stop6h 15m
Southwest
Deal found 7/15![Southwest logo]()
$124
This Super.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/229:20 pm
ORD
- SJC
1 stop23h 59m
Frontier
Deal found 7/14![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/910:40 pm
ORD
- SJC
2 stops23h 28m
Frontier
Deal found 7/15![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:41 pm
ORD
- SJC
2 stops30h 38m
Frontier
Deal found 7/16![Frontier logo]()
$128
This Delta deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:11 am
MDW
- SJC
1 stop7h 17m
Delta
Deal found 7/14![Delta logo]()
$129
This Delta deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/112:36 pm
ORD
- SJC
1 stop9h 37m
Delta
Deal found 7/14![Delta logo]()
$129
This Priceline deal was found by Cheapflights users on 7/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:29 am
ORD
- SJC
1 stop7h 48m
Frontier
Deal found 7/18![Frontier logo]()
$130
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 July 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $262 (Southwest) |
One-way from | $118 (Super.com) |
Popular in | February |
Cheapest in | January |
Average price | $460 |
Good round-trip deal | $399 or less |
Good one-way deal | $248 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 2,558,603 searches. Data last updated July 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
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Wed 10/28
1:05 pm-7:00 pm
2 stops7h 55m
San Jose
Wed 11/4
9:45 am-7:55 pm
2 stops8h 10m
$267
Quickest round-trip
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Mon 8/24
8:50 pm-11:20 pm
Nonstop4h 30m
San Jose
Wed 8/26
11:00 pm-5:00 am
Nonstop4h 00m
$277
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Thu 8/20
12:45 pm-5:31 pm
1 stop6h 46m
San Jose
Mon 8/24
2:10 pm-8:35 pm
Nonstop4h 25m
$278
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Thu 10/1
8:17 pm-9:23 am
1 stop15h 06m
San Jose
Sun 10/4
5:18 pm-1:25 pm
1 stop18h 07m
$302
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Sat 8/29
2:15 pm-9:20 pm
2 stops9h 05m
San Jose
Sat 9/5
10:45 am-8:15 pm
1 stop7h 30m
$302
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Sat 8/22
1:45 pm-7:35 pm
2 stops7h 50m
San Jose
Mon 8/24
7:55 am-5:10 pm
2 stops7h 15m
$307
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Tue 10/6
7:20 am-2:55 pm
1 stop9h 35m
San Jose
Wed 10/7
8:54 am-6:53 pm
1 stop7h 59m
$319
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Thu 10/1
9:15 pm-11:50 pm
Nonstop4h 35m
San Jose
Sun 10/4
8:25 am-6:00 pm
2 stops7h 35m
$337
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Sat 9/12
3:56 pm-8:54 pm
1 stop6h 58m
San Jose
Sat 9/19
6:30 am-12:55 pm
Nonstop4h 25m
$347
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Wed 9/2
2:42 pm-8:57 pm
1 stop8h 15m
San Jose
Mon 9/7
6:20 am-12:45 pm
Nonstop4h 25m
$369
Showing 1-10 of 43 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 July.
| 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 | |
| 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
ORD-SJC
MDW-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
ORD-SJC
MDW-SJC
What is the cheapest month to book a flight from Chicago to San Jose, California?
Currently, October is the cheapest month in which you can book a flight from Chicago to San Jose, California (average of $389). Flying from Chicago to San Jose, California in February is currently the most expensive (average of $582). 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 July 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 morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 22% on airfare.
Weekly flight availability from Chicago to San Jose, California
Explore weekly flight availability from Chicago to San Jose. 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 July 19, 2026.
The most flights from CHI to SJC 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 (2 on average).
How much does it cost to fly round-trip from Chicago to San Jose, California?
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 July 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.
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Chicago
Popular flights
San Jose flight routes
Alternative routes for Chicago to San Jose
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to San Jose by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to San Jose by cabin class
Find flights from Chicago to San Jose, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and San Jose flights
Browse other Chicago and San Jose flight options. Last updated on July 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 July 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 July 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 2,558,603 searches. Data last updated July 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$136 | Average$350 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$232 | Average$366 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$325 | Average$479 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$332 | Average$484 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$352 | Average$625 | FlexibilityNo cancel fee | On-time71% |