$113+ 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 8/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJC
Jul 3 — Jul 101
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 56 days in advance, depart on a Wednesday or Tuesday 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 June 3, 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 June 3, 2026.
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 9/233:30 pm
MDW
- SJC
1 stop7h 20m
Southwest
Wed 9/301:25 pm
SJC
- MDW
1 stop7h 25m
Southwest
Deal found 6/2![Southwest logo]()
$268
This United Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 8/208:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Tue 9/112:51 pm
SJC
- ORD
1 stop6h 38m
United Airlines
Deal found 6/2![United Airlines logo]()
$271
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:05 am
MDW
- SJC
1 stop7h 31m
Delta
Tue 10/1310:20 pm
SJC
- MDW
1 stop9h 32m
Delta
Deal found 6/2![Delta logo]()
$273
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/17:37 pm
ORD
- SJC
1 stop6h 02m
Delta
Wed 7/82:55 pm
SJC
- ORD
1 stop6h 43m
Delta
Deal found 6/2![Delta logo]()
$273
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 8/261:51 pm
MDW
- SJC
1 stop8h 33m
Delta
Tue 9/16:00 am
SJC
- MDW
2 stops10h 01m
Delta
Deal found 6/2![Delta logo]()
$278
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/17:37 pm
ORD
- SJC
1 stop6h 02m
Delta
Tue 7/78:25 pm
SJC
- ORD
2 stops10h 05m
Delta
Deal found 6/2![Delta logo]()
$278
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 10/36:05 am
MDW
- SJC
1 stop7h 31m
Delta
Tue 10/610:20 pm
SJC
- MDW
1 stop9h 32m
Delta
Deal found 6/2![Delta logo]()
$281
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 7/286:30 am
ORD
- SJC
1 stop7h 31m
Delta
Mon 9/211:23 pm
SJC
- ORD
1 stop6h 10m
Delta
Deal found 6/1![Delta logo]()
$281
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 6/309:54 am
MDW
- SJC
2 stops9h 23m
Delta
Wed 7/88:25 pm
SJC
- MDW
2 stops10h 12m
Delta
Deal found 6/1![Delta logo]()
$284
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 7/82:02 pm
ORD
- SJC
2 stops10h 11m
Delta
Tue 7/147:00 am
SJC
- ORD
2 stops12h 29m
Delta
Deal found 6/1![Delta logo]()
$284
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 9/149:49 am
MDW
- SJC
2 stops9h 24m
Delta
Wed 10/146:30 am
SJC
- MDW
1 stop8h 20m
Delta
Deal found 6/2![Delta logo]()
$286
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 7/287:40 pm
ORD
- SJC
1 stop5h 59m
Delta
Sat 9/268:25 pm
SJC
- ORD
2 stops11h 44m
Delta
Deal found 6/1![Delta logo]()
$286
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 June 3, 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 June 3, 2026.
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:05 am
MDW
- SJC
1 stop7h 31m
Delta
Tue 10/1310:20 pm
SJC
- MDW
1 stop9h 32m
Delta
Deal found 6/2![Delta logo]()
$273
This United Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 6/307:55 pm
ORD
- SJC
Nonstop4h 45m
United Airlines
Thu 7/21:10 pm
SJC
- ORD
1 stop9h 35m
United Airlines
Deal found 6/2![United Airlines logo]()
$340
This Alaska Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/97:59 pm
ORD
- SJC
1 stop15h 27m
Alaska Airlines
Thu 7/168:00 am
SJC
- ORD
1 stop19h 00m
Alaska Airlines
Deal found 6/2![Alaska Airlines logo]()
$347
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/18:55 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Tue 7/710:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 6/2![Southwest logo]()
$350
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 10/209:55 am
MDW
- SJC
2 stops8h 21m
Delta
Mon 10/266:30 am
SJC
- MDW
1 stop8h 20m
Delta
Deal found 6/2![Delta logo]()
$286
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 8/131:51 pm
MDW
- SJC
1 stop8h 33m
Delta
Mon 8/176:59 am
SJC
- MDW
2 stops9h 34m
Delta
Deal found 5/30![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 6/2012:15 pm
MDW
- SJC
1 stop7h 55m
Southwest
Wed 7/2210:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 5/29![Southwest logo]()
$360
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 9/149:49 am
MDW
- SJC
2 stops9h 24m
Delta
Mon 10/128:05 pm
SJC
- MDW
2 stops10h 40m
Delta
Deal found 6/2![Delta logo]()
$300
This United Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 8/1312:45 pm
ORD
- SJC
1 stop6h 46m
United Airlines
Mon 8/172:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Deal found 5/30![United Airlines logo]()
$423
This Southwest deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 7/218:55 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Tue 7/2810:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 5/31![Southwest logo]()
$407
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 7/109:54 am
MDW
- SJC
2 stops10h 32m
Delta
Tue 7/1410:00 pm
SJC
- MDW
2 stops12h 38m
Delta
Deal found 5/30![Delta logo]()
$360
This United Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 6/277:55 pm
ORD
- SJC
Nonstop4h 45m
United Airlines
Tue 6/304:00 pm
SJC
- ORD
1 stop6h 44m
United Airlines
Deal found 5/30![United Airlines logo]()
$437
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:15 am
MDW
- SJC
1 stop6h 15m
Southwest
Sun 9/2711:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Deal found 6/2![Southwest logo]()
$413
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/197:29 am
ORD
- SJC
1 stop8h 43m
Delta
Tue 7/218:25 pm
SJC
- ORD
2 stops10h 05m
Delta
Deal found 6/2![Delta logo]()
$388
This United Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/167:58 pm
ORD
- SJC
Nonstop4h 45m
United Airlines
Sun 7/196:30 am
SJC
- ORD
Nonstop4h 24m
United Airlines
Deal found 6/2![United Airlines logo]()
$485
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 7/73:55 pm
ORD
- SJC
1 stop6h 40m
Delta
Thu 7/97:00 am
SJC
- ORD
2 stops12h 29m
Delta
Deal found 5/30![Delta logo]()
$428
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 8/2811:22 am
ORD
- SJC
2 stops11h 02m
Delta
Sun 8/301:46 pm
SJC
- ORD
1 stop6h 12m
Delta
Deal found 5/31![Delta logo]()
$432
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 7/168:27 am
ORD
- SJC
2 stops9h 19m
Delta
Thu 7/238:25 pm
SJC
- ORD
2 stops10h 05m
Delta
Deal found 6/1![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/237:29 am
ORD
- SJC
1 stop8h 43m
Delta
Mon 7/276:12 pm
SJC
- ORD
2 stops12h 23m
Delta
Deal found 6/2![Delta logo]()
$498
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/312:02 pm
ORD
- SJC
2 stops10h 11m
Delta
Sun 8/28:25 pm
SJC
- ORD
2 stops10h 05m
Delta
Deal found 6/2![Delta logo]()
$503
Last-minute flights from Chicago to San JoseDiscover last-minute flight deals from Chicago to San Jose. Data last updated June 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San Jose. Data last updated June 3, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 6/247:50 pm
ORD
- SJC
Nonstop4h 45m
United Airlines
Tue 6/304:00 pm
SJC
- ORD
1 stop6h 44m
United Airlines
Deal found 5/29![United Airlines logo]()
$287
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 6/309:54 am
MDW
- SJC
2 stops9h 23m
Delta
Wed 7/812:40 pm
SJC
- MDW
1 stop7h 35m
Delta
Deal found 6/1![Delta logo]()
$278
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 6/309:54 am
MDW
- SJC
2 stops9h 23m
Delta
Tue 7/78:25 pm
SJC
- MDW
2 stops10h 12m
Delta
Deal found 6/1![Delta logo]()
$284
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/306:30 am
ORD
- SJC
2 stops11h 23m
Delta
Tue 7/78:25 pm
SJC
- ORD
2 stops10h 05m
Delta
Deal found 6/3![Delta logo]()
$284
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/16:00 am
MDW
- SJC
1 stop7h 25m
Southwest
Tue 7/78:55 pm
SJC
- MDW
1 stop6h 30m
Southwest
Deal found 6/2![Southwest logo]()
$273
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/17:37 pm
ORD
- SJC
1 stop6h 02m
Delta
Wed 7/82:55 pm
SJC
- ORD
1 stop6h 43m
Delta
Deal found 6/2![Delta logo]()
$273
This United Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/17:58 pm
ORD
- SJC
Nonstop4h 45m
United Airlines
Tue 7/76:30 am
SJC
- ORD
Nonstop4h 24m
United Airlines
Deal found 6/2![United Airlines logo]()
$291
This United Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/17:58 pm
ORD
- SJC
Nonstop4h 45m
United Airlines
Wed 7/81:10 pm
SJC
- ORD
1 stop9h 35m
United Airlines
Deal found 6/3![United Airlines logo]()
$302
This Alaska Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/156:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Wed 7/227:13 am
SJC
- ORD
1 stop9h 44m
Alaska Airlines
Deal found 6/3![Alaska Airlines logo]()
$293
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 7/287:40 pm
ORD
- SJC
1 stop5h 59m
Delta
Sat 9/266:10 am
SJC
- ORD
1 stop6h 58m
Delta
Deal found 6/1![Delta logo]()
$281
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 7/287:40 pm
ORD
- SJC
1 stop5h 59m
Delta
Mon 9/218:53 pm
SJC
- ORD
2 stops9h 37m
Delta
Deal found 6/1![Delta logo]()
$286
This Alaska Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 7/286:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Tue 8/46:37 pm
SJC
- ORD
1 stop8h 23m
Alaska Airlines
Deal found 5/30![Alaska Airlines logo]()
$301
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 June 3, 2026.
Search for one-way flight options from Chicago to San Jose. Find affordable one-way fares based on user searches. Data last updated June 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 8/229:07 pm
ORD
- SJC
1 stop16h 55m
Frontier
Deal found 5/31![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 7/89:13 pm
ORD
- SJC
1 stop24h 15m
Frontier
Deal found 5/30![Frontier logo]()
$119
This Southwest deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 8/2610:20 am
MDW
- SJC
Nonstop4h 25m
Southwest
Deal found 5/30![Southwest logo]()
$135
This United Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 5/31![United Airlines logo]()
$135
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 6/306:00 am
MDW
- SJC
1 stop7h 25m
Southwest
Deal found 5/29![Southwest logo]()
$137
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 6/306:55 am
ORD
- SJC
1 stop9h 16m
Delta
Deal found 5/29![Delta logo]()
$137
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 6/309:54 am
MDW
- SJC
2 stops9h 23m
Delta
Deal found 5/29![Delta logo]()
$142
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 7/82:02 pm
ORD
- SJC
2 stops10h 11m
Delta
Deal found 5/30![Delta logo]()
$142
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 8/226:05 am
MDW
- SJC
1 stop7h 23m
Delta
Deal found 6/2![Delta logo]()
$145
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 8/227:45 am
ORD
- SJC
1 stop6h 20m
Delta
Deal found 6/1![Delta logo]()
$145
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 8/276:05 am
MDW
- SJC
2 stops11h 45m
Delta
Deal found 6/1![Delta logo]()
$150
This Alaska Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/76:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 6/3![Alaska Airlines logo]()
$157
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 June 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $268 (Southwest) |
One-way from | $113 (Kiwi.com) |
Popular in | February |
Cheapest in | January |
Average price | $456 |
Good round-trip deal | $407 or less |
Good one-way deal | $173 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 June 3, 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
Tue 9/15
6:05 am-11:36 am
1 stop7h 31m
San Jose
Tue 10/13
10:20 pm-9:52 am
1 stop9h 32m
$273
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Tue 10/20
9:55 am-4:16 pm
2 stops8h 21m
San Jose
Mon 10/26
6:30 am-4:50 pm
1 stop8h 20m
$286
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Thu 8/13
1:51 pm-8:24 pm
1 stop8h 33m
San Jose
Mon 8/17
6:59 am-6:33 pm
2 stops9h 34m
$294
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Mon 9/14
9:49 am-5:13 pm
2 stops9h 24m
San Jose
Mon 10/12
8:05 pm-8:45 am
2 stops10h 40m
$300
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Tue 6/30
7:55 pm-10:40 pm
Nonstop4h 45m
San Jose
Thu 7/2
1:10 pm-12:45 am
1 stop9h 35m
$340
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Thu 7/9
7:59 pm-9:26 am
1 stop15h 27m
San Jose
Thu 7/16
8:00 am-5:00 am
1 stop19h 00m
$347
Quickest round-trip
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Wed 7/1
8:55 pm-11:25 pm
Nonstop4h 30m
San Jose
Tue 7/7
10:55 pm-5:00 am
Nonstop4h 05m
$350
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Sat 6/20
12:15 pm-6:10 pm
1 stop7h 55m
San Jose
Wed 7/22
10:55 pm-5:00 am
Nonstop4h 05m
$360
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Fri 7/10
9:54 am-6:26 pm
2 stops10h 32m
San Jose
Tue 7/14
10:00 pm-12:38 pm
2 stops12h 38m
$360
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Sun 7/19
7:29 am-2:12 pm
1 stop8h 43m
San Jose
Tue 7/21
8:25 pm-8:30 am
2 stops10h 05m
$388
Showing 1-10 of 44 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 June.
| 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
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, 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 March is currently the most expensive (average of $297). 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 June 3, 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 June 3, 2026.
The most flights from CHI to SJC are scheduled on a Tuesday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 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 55 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 June 3, 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.
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
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 June 3, 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 June 3, 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 June 3, 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 June 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$138 | Average$384 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$232 | Average$363 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$299 | Average$485 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$331 | Average$481 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$406 | Average$545 | FlexibilityNo cancel fee | On-time71% |