$86+ 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 6/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJC
Mar 21 — Mar 281
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 2 days in advance, depart on a Thursday or Wednesday and return on a Tuesday
Cheap flight deals from Chicago to San Jose
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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 February 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 February 19, 2026.
This Southwest deal was found by Cheapflights users on 2/18. 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.
Thu 3/128:00 pm
MDW
- SJC
Nonstop4h 40m
Southwest
Mon 3/1611:40 am
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 2/18![Southwest logo]()
$326
This Expedia deal was found by Cheapflights users on 2/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/243:07 pm
ORD
- SJC
1 stop9h 49m
Multiple Airlines
Fri 2/278:50 am
SJC
- ORD
1 stop6h 36m
Multiple Airlines
Deal found 2/18![Multiple Airlines logo]()
$326
This CheapOair deal was found by Cheapflights users on 2/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/212:10 pm
ORD
- SJC
1 stop10h 49m
Alaska Airlines
Mon 5/257:59 pm
SJC
- ORD
1 stop15h 15m
Alaska Airlines
Deal found 2/18![Alaska Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 2/17. 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.
Thu 4/96:00 am
MDW
- SJC
2 stops7h 45m
Southwest
Mon 4/138:40 pm
SJC
- MDW
1 stop7h 10m
Southwest
Deal found 2/17![Southwest logo]()
$328
This Delta deal was found by Cheapflights users on 2/18. 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 3/127:20 am
ORD
- SJC
1 stop7h 11m
Delta
Thu 3/197:00 am
SJC
- ORD
2 stops9h 05m
Delta
Deal found 2/18![Delta logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 2/16. 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 3/23:54 pm
ORD
- SJC
1 stop9h 05m
Hawaiian Airlines
Thu 3/512:45 pm
SJC
- ORD
1 stop9h 14m
Hawaiian Airlines
Deal found 2/16![Hawaiian Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 2/16. 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 4/248:25 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Tue 4/2810:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 2/16![Southwest logo]()
$330
This CheapOair deal was found by Cheapflights users on 2/16. 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.
Thu 3/53:07 pm
ORD
- SJC
1 stop9h 49m
Alaska Airlines
Sun 3/87:00 am
SJC
- ORD
1 stop14h 59m
Alaska Airlines
Deal found 2/16![Alaska Airlines logo]()
$330
This Expedia deal was found by Cheapflights users on 2/15. 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 2/198:20 am
ORD
- SJC
1 stop7h 56m
Multiple Airlines
Thu 2/2610:34 am
SJC
- ORD
1 stop28h 52m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 2/17. 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.
Thu 4/28:00 pm
MDW
- SJC
Nonstop4h 40m
Southwest
Tue 4/1410:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 2/17![Southwest logo]()
$332
This United Airlines deal was found by Cheapflights users on 2/16. 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.
Tue 3/177:59 pm
ORD
- SJC
Nonstop5h 00m
United Airlines
Sun 3/2210:55 pm
SJC
- ORD
Nonstop4h 19m
United Airlines
Deal found 2/16![United Airlines logo]()
$332
This Delta deal was found by Cheapflights users on 2/17. 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.
Fri 5/151:22 pm
MDW
- SJC
2 stops10h 52m
Delta
Mon 5/187:59 pm
SJC
- MDW
2 stops10h 44m
Delta
Deal found 2/17![Delta logo]()
$333
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 February 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 February 19, 2026.
This Southwest deal was found by Cheapflights users on 2/17. 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.
Thu 4/910:10 am
MDW
- SJC
Nonstop4h 35m
Southwest
Mon 4/1310:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 2/17![Southwest logo]()
$326
This Delta deal was found by Cheapflights users on 2/18. 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.
Mon 4/202:12 pm
MDW
- SJC
1 stop8h 25m
Delta
Thu 4/238:20 pm
SJC
- MDW
2 stops10h 27m
Delta
Deal found 2/18![Delta logo]()
$328
This United Airlines deal was found by Cheapflights users on 2/16. 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.
Tue 3/177:59 pm
ORD
- SJC
Nonstop5h 00m
United Airlines
Sun 3/2210:55 pm
SJC
- ORD
Nonstop4h 19m
United Airlines
Deal found 2/16![United Airlines logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/186:20 am
ORD
- SJC
1 stop15h 05m
Multiple Airlines
Fri 5/222:45 pm
SJC
- ORD
1 stop14h 15m
Multiple Airlines
Deal found 2/18![Multiple Airlines logo]()
$351
This CheapOair deal was found by Cheapflights users on 2/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/227:49 pm
ORD
- SJC
1 stop15h 33m
Alaska Airlines
Thu 5/287:06 am
SJC
- ORD
1 stop9h 44m
Alaska Airlines
Deal found 2/18![Alaska Airlines logo]()
$353
This Delta deal was found by Cheapflights users on 2/18. 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 3/127:20 am
ORD
- SJC
1 stop7h 11m
Delta
Thu 3/197:00 am
SJC
- ORD
2 stops9h 05m
Delta
Deal found 2/18![Delta logo]()
$328
This Southwest deal was found by Cheapflights users on 2/18. 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.
Wed 5/63:40 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Sun 5/104:35 pm
SJC
- MDW
1 stop6h 25m
Southwest
Deal found 2/18![Southwest logo]()
$342
This Alaska Airlines deal was found by Cheapflights users on 2/17. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:00 am
ORD
- SJC
1 stop7h 18m
Alaska Airlines
Wed 7/86:00 am
SJC
- ORD
2 stops21h 00m
Alaska Airlines
Deal found 2/17![Alaska Airlines logo]()
$357
This United Airlines deal was found by Cheapflights users on 2/15. 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 4/167:41 pm
ORD
- SJC
Nonstop4h 55m
United Airlines
Sat 4/188:45 am
SJC
- ORD
1 stop8h 09m
United Airlines
Deal found 2/15![United Airlines logo]()
$366
This Delta deal was found by Cheapflights users on 2/15. 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.
Fri 5/151:22 pm
MDW
- SJC
2 stops10h 52m
Delta
Mon 5/187:59 pm
SJC
- MDW
2 stops10h 43m
Delta
Deal found 2/15![Delta logo]()
$333
This Southwest deal was found by Cheapflights users on 2/17. 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.
Thu 4/210:05 am
MDW
- SJC
Nonstop4h 40m
Southwest
Mon 4/1310:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 2/17![Southwest logo]()
$345
This Delta deal was found by Cheapflights users on 2/18. 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.
Mon 4/207:35 am
ORD
- SJC
2 stops11h 24m
Delta
Thu 4/238:20 pm
SJC
- ORD
2 stops10h 18m
Delta
Deal found 2/18![Delta logo]()
$333
This Southwest deal was found by Cheapflights users on 2/16. 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 4/243:05 pm
MDW
- SJC
1 stop6h 35m
Southwest
Tue 4/281:35 pm
SJC
- MDW
1 stop5h 55m
Southwest
Deal found 2/16![Southwest logo]()
$350
This Delta deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/72:11 pm
ORD
- SJC
2 stops10h 25m
Delta
Mon 5/119:53 am
SJC
- ORD
2 stops9h 57m
Delta
Deal found 2/16![Delta logo]()
$333
This Southwest deal was found by Cheapflights users on 2/17. 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.
Fri 5/85:25 am
MDW
- SJC
1 stop6h 55m
Southwest
Fri 5/810:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 2/17![Southwest logo]()
$353
This Delta deal was found by Cheapflights users on 2/16. 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 4/1412:52 pm
MDW
- SJC
1 stop10h 53m
Delta
Sun 4/196:00 pm
SJC
- MDW
2 stops12h 47m
Delta
Deal found 2/16![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 2/15. 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 5/16:15 am
MDW
- SJC
1 stop6h 15m
Southwest
Mon 5/42:40 pm
SJC
- MDW
1 stop6h 00m
Southwest
Deal found 2/15![Southwest logo]()
$358
This Delta deal was found by Cheapflights users on 2/17. 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.
Wed 5/206:30 am
ORD
- SJC
2 stops9h 41m
Delta
Sun 5/247:36 am
SJC
- ORD
1 stop7h 28m
Delta
Deal found 2/17![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 2/17. 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 3/2311:50 am
MDW
- SJC
1 stop6h 35m
Southwest
Thu 3/2610:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 2/17![Southwest logo]()
$359
This Delta deal was found by Cheapflights users on 2/19. 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 4/1412:14 pm
ORD
- SJC
2 stops8h 53m
Delta
Sun 4/268:20 pm
SJC
- ORD
2 stops10h 18m
Delta
Deal found 2/19![Delta logo]()
$362
This Delta deal was found by Cheapflights users on 2/18. 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.
Mon 5/182:00 pm
ORD
- SJC
1 stop9h 40m
Delta
Thu 5/2110:55 pm
SJC
- ORD
1 stop7h 03m
Delta
Deal found 2/18![Delta logo]()
$365
Last-minute flights from Chicago to San JoseDiscover last-minute flight deals from Chicago to San Jose. Data last updated February 19, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San Jose. Data last updated February 19, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 2/15. 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 2/198:20 am
ORD
- SJC
1 stop7h 56m
Multiple Airlines
Thu 2/2610:34 am
SJC
- ORD
1 stop28h 52m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$331
This Expedia deal was found by Cheapflights users on 2/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/243:07 pm
ORD
- SJC
1 stop9h 49m
Multiple Airlines
Fri 2/278:50 am
SJC
- ORD
1 stop6h 36m
Multiple Airlines
Deal found 2/18![Multiple Airlines logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 2/16. 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 3/23:54 pm
ORD
- SJC
1 stop9h 05m
Hawaiian Airlines
Thu 3/512:45 pm
SJC
- ORD
1 stop9h 14m
Hawaiian Airlines
Deal found 2/16![Hawaiian Airlines logo]()
$329
This CheapOair deal was found by Cheapflights users on 2/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/58:20 am
ORD
- SJC
1 stop7h 56m
Alaska Airlines
Sun 3/87:00 am
SJC
- ORD
1 stop14h 59m
Alaska Airlines
Deal found 2/17![Alaska Airlines logo]()
$330
This Alaska Airlines deal was found by Cheapflights users on 2/18. 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.
Fri 3/63:07 pm
ORD
- SJC
1 stop9h 49m
Alaska Airlines
Sat 3/72:36 pm
SJC
- ORD
1 stop7h 20m
Alaska Airlines
Deal found 2/18![Alaska Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/96:05 am
MDW
- SJC
1 stop6h 50m
Southwest
Tue 3/179:50 pm
SJC
- MDW
1 stop7h 55m
Southwest
Deal found 2/16![Southwest logo]()
$333
This CheapOair deal was found by Cheapflights users on 2/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/102:07 pm
ORD
- SJC
2 stops10h 49m
Alaska Airlines
Mon 3/162:53 pm
SJC
- ORD
1 stop7h 06m
Alaska Airlines
Deal found 2/17![Alaska Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 2/18. 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.
Thu 3/128:00 pm
MDW
- SJC
Nonstop4h 40m
Southwest
Mon 3/1611:40 am
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 2/18![Southwest logo]()
$326
This Delta deal was found by Cheapflights users on 2/18. 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 3/127:20 am
ORD
- SJC
1 stop7h 11m
Delta
Thu 3/197:00 am
SJC
- ORD
2 stops9h 05m
Delta
Deal found 2/18![Delta logo]()
$328
This United Airlines deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/127:59 pm
ORD
- SJC
Nonstop5h 00m
United Airlines
Wed 3/183:49 pm
SJC
- ORD
1 stop6h 03m
United Airlines
Deal found 2/17![United Airlines logo]()
$334
This United Airlines deal was found by Cheapflights users on 2/16. 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.
Tue 3/177:59 pm
ORD
- SJC
Nonstop5h 00m
United Airlines
Sun 3/2210:55 pm
SJC
- ORD
Nonstop4h 19m
United Airlines
Deal found 2/16![United Airlines logo]()
$332
This Delta deal was found by Cheapflights users on 2/15. 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 3/231:19 pm
ORD
- SJC
2 stops10h 43m
Delta
Wed 3/256:20 am
SJC
- ORD
2 stops8h 23m
Delta
Deal found 2/15![Delta logo]()
$333
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 February 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 February 19, 2026.
This CheapOair deal was found by Cheapflights users on 2/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/49:00 am
ORD
- SJC
1 stop7h 13m
Alaska Airlines
Deal found 2/17![Alaska Airlines logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 4/159:18 pm
ORD
- SJC
1 stop22h 44m
Frontier
Deal found 2/17![Frontier logo]()
$87
This Trip.com deal was found by Cheapflights users on 2/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/37:21 pm
ORD
- SJC
1 stop26h 06m
Frontier
Deal found 2/19![Frontier logo]()
$88
This Expedia deal was found by Cheapflights users on 2/19. 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.
Wed 5/63:52 pm
ORD
- SJC
1 stop19h 52m
Alaska Airlines
Deal found 2/19![Alaska Airlines logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 2/17. 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.
Sun 4/266:15 am
MDW
- SJC
2 stops39h 10m
Frontier
Deal found 2/17![Frontier logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 2/16. 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 3/97:00 am
ORD
- SJC
2 stops13h 07m
Frontier
Deal found 2/16![Frontier logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
Sun 3/159:08 pm
ORD
- SJC
2 stops23h 39m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 2/16. 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 5/135:09 pm
ORD
- SJC
1 stop26h 53m
Multiple Airlines
Deal found 2/16![Multiple Airlines logo]()
$99
This Alaska Airlines deal was found by Cheapflights users on 2/17. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/112:07 pm
ORD
- SJC
1 stop7h 18m
Alaska Airlines
Deal found 2/17![Alaska Airlines logo]()
$105
This CheapOair deal was found by Cheapflights users on 2/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/248:48 pm
ORD
- SJC
1 stop19h 02m
Alaska Airlines
Deal found 2/19![Alaska Airlines logo]()
$110
This Trip.com deal was found by Cheapflights users on 2/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/159:08 pm
ORD
- SJC
1 stop14h 17m
Frontier
Deal found 2/15![Frontier logo]()
$111
This Delta deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/289:30 am
MDW
- SJC
2 stops14h 06m
Delta
Deal found 2/15![Delta logo]()
$124
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 February 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $326 (Southwest) |
One-way from | $86 (CheapOair) |
Popular in | February |
Cheapest in | January |
Average price | $622 |
Good round-trip deal | $349 or less |
Good one-way deal | $268 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 February 19, 2026.
Use the filters below to find and compare flights from Chicago to San Jose that are best for you.
Fly from
Chicago
Fly to
San Jose
Route
Depart
Return
Price
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Thu 4/9
10:10 am-12:45 pm
Nonstop4h 35m
San Jose
Mon 4/13
10:55 pm-5:00 am
Nonstop4h 05m
$326
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Mon 4/20
2:12 pm-8:37 pm
1 stop8h 25m
San Jose
Thu 4/23
8:20 pm-8:47 am
2 stops10h 27m
$328
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Thu 3/12
7:20 am-12:31 pm
1 stop7h 11m
San Jose
Thu 3/19
7:00 am-6:05 pm
2 stops9h 05m
$328
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Tue 3/17
7:59 pm-10:59 pm
Nonstop5h 00m
San Jose
Sun 3/22
10:55 pm-5:14 am
Nonstop4h 19m
$332
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Fri 5/15
1:22 pm-10:14 pm
2 stops10h 52m
San Jose
Mon 5/18
7:59 pm-8:42 am
2 stops10h 43m
$333
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Mon 4/20
7:35 am-4:59 pm
2 stops11h 24m
San Jose
Thu 4/23
8:20 pm-8:38 am
2 stops10h 18m
$333
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Thu 5/7
2:11 pm-10:36 pm
2 stops10h 25m
San Jose
Mon 5/11
9:53 am-9:50 pm
2 stops9h 57m
$333
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Wed 5/6
3:40 pm-6:15 pm
Nonstop4h 35m
San Jose
Sun 5/10
4:35 pm-1:00 am
1 stop6h 25m
$342
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Thu 4/2
10:05 am-12:45 pm
Nonstop4h 40m
San Jose
Mon 4/13
10:55 pm-5:00 am
Nonstop4h 05m
$345
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Fri 4/24
3:05 pm-7:40 pm
1 stop6h 35m
San Jose
Tue 4/28
1:35 pm-9:30 pm
1 stop5h 55m
$350
Showing 1-10 of 41 results
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 February.
| 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 Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- 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
How far ahead should I book a flight from Chicago to San Jose, California?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to San Jose. Price data was last updated on February 13, 2026.
Booking 2 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.
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 $80). Flying from Chicago to San Jose, California in February is currently the most expensive (average of $211). 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 February 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 at noon could potentially save you up to 34% on airfare.
How much does it cost to fly round-trip from Chicago to San Jose, California?
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 February 19, 2026.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and United Airlines 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.
Crew
8.5
Comfort
7.8
Entertainment
7.0
Overall
8.0
Food
7.1
Boarding
8.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Crew
8.5
Comfort
7.8
Entertainment
7.0
Overall
8.0
Food
7.1
Boarding
8.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Crew
8.5
Comfort
7.8
Entertainment
7.0
Overall
8.0
Food
7.1
Boarding
8.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Crew
8.5
Comfort
7.8
Entertainment
7.0
Overall
8.0
Food
7.1
Boarding
8.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Crew
8.5
Comfort
7.8
Entertainment
7.0
Overall
8.0
Food
7.1
Boarding
8.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Crew
8.5
Comfort
7.8
Entertainment
7.0
Overall
8.0
Food
7.1
Boarding
8.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
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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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 February 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 February 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 February 19, 2026.
Top 7 airlines flying from Chicago to San Jose
Discover the top 7 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 February 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$80 | Average$193 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$142 | Average$198 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$189 | Average$384 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$262 | Average$366 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$333 | Average$470 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$337 | Average$479 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$370 | Average$545 | FlexibilityNo cancel fee | On-time71% |