For a quick departure, use the 'L' train from downtown Chicago to avoid traffic delays when heading to ORD.

Most accurate provider | Mytrip 3 stars |
|---|---|
Most trusted provider | Mytrip 3 stars |
Round-trip from | $227 (Kiwi.com) |
One-way from | $71 (CheapOair) |
Popular in | June |
Cheapest in | September |
Average price | $422 |
Good round-trip deal | $475 or less |
Good one-way deal | $238 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Tue 12/16
8:59 pm-11:58 am
1 stop16h 59m
San Jose
Mon 1/5
8:00 pm-2:37 pm
1 stop16h 37m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Tue 2/24
3:07 pm-10:56 pm
1 stop9h 49m
San Jose
Wed 2/25
10:26 am-11:59 pm
1 stop11h 33m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Wed 12/3
8:59 pm-11:58 am
1 stop16h 59m
San Jose
Sat 12/6
12:35 pm-11:50 pm
1 stop9h 15m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Sun 12/14
8:59 pm-11:58 am
1 stop16h 59m
San Jose
Mon 1/5
8:00 pm-2:37 pm
1 stop16h 37m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Fri 12/5
8:55 am-2:32 pm
1 stop7h 37m
San Jose
Mon 12/8
7:57 pm-7:54 pm
1 stop21h 57m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Sat 12/13
7:50 am-6:56 pm
1 stop13h 06m
San Jose
Tue 12/30
12:22 pm-11:59 pm
1 stop9h 37m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Thu 12/4
7:50 am-7:18 pm
2 stops13h 28m
San Jose
Tue 12/16
11:40 am-11:59 pm
1 stop10h 19m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Mon 12/8
2:14 pm-11:53 pm
2 stops11h 39m
San Jose
Thu 12/11
2:25 pm-11:59 pm
1 stop7h 34m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Mon 12/8
7:50 am-6:18 pm
2 stops12h 28m
San Jose
Wed 12/10
11:40 am-11:59 pm
1 stop10h 19m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Tue 12/9
7:50 am-6:18 pm
2 stops12h 28m
San Jose
Thu 12/11
2:25 pm-11:59 pm
1 stop7h 34m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
Booking 85 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago O'Hare Intl Airport to San Jose, California. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Currently, October is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to San Jose, California (average of $80). Flying from Chicago O'Hare Intl Airport to San Jose, California in June is currently the most expensive (average of $198). 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.
When flying from Chicago O'Hare Intl Airport to San Jose, California, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 52% versus a flight in the morning.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to San Jose, California flight should consider departing on Wednesday at noon when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Boarding
Crew
Comfort
Entertainment
Food
Overall
Reviews
Walter,Aug 2025
OAK - SAN
Boarding
Crew
Comfort
Entertainment
Food
Overall
Reviews
Walter,Aug 2025
OAK - SAN
Boarding
Crew
Comfort
Entertainment
Food
Overall
Reviews
Walter,Aug 2025
OAK - SAN
Boarding
Crew
Comfort
Entertainment
Food
Overall
Reviews
Walter,Aug 2025
OAK - SAN
Boarding
Crew
Comfort
Entertainment
Food
Overall
Reviews
Walter,Aug 2025
OAK - SAN
Boarding
Crew
Comfort
Entertainment
Food
Overall
Reviews
Walter,Aug 2025
OAK - SAN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$80 | Average$238 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$142 | Average$220 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$260 | Average$338 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$265 | Average$384 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$340 | Average$506 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$348 | Average$496 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$352 | Average$620 | FlexibilityNo cancel fee | On-time71% |