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 | $240 (Expedia) |
One-way from | $91 (Frontier) |
Popular in | November |
Cheapest in | September |
Average price | $455 |
Good round-trip deal | $477 or less |
Good one-way deal | $268 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Sat 1/17
3:44 pm-10:35 pm
1 stop8h 51m
San Jose
Tue 1/20
12:46 pm-11:37 pm
1 stop8h 51m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Fri 1/9
9:00 am-12:09 pm
1 stop29h 09m
San Jose
Fri 1/23
10:29 am-2:29 pm
1 stop26h 00m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Wed 1/7
3:44 pm-9:47 am
1 stop20h 03m
San Jose
Wed 1/14
7:52 pm-2:29 pm
1 stop16h 37m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Mon 1/12
6:06 pm-1:08 pm
1 stop21h 02m
San Jose
Mon 1/19
7:00 am-2:29 pm
1 stop29h 29m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Thu 1/15
3:44 pm-10:35 pm
1 stop8h 51m
San Jose
Thu 1/22
9:05 am-11:50 pm
1 stop12h 45m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Fri 1/16
7:30 am-1:34 pm
1 stop8h 04m
San Jose
Mon 1/19
7:45 am-1:22 pm
1 stop27h 37m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Thu 1/15
2:20 pm-10:55 pm
2 stops10h 35m
San Jose
Thu 1/22
11:40 am-11:53 pm
1 stop10h 13m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Wed 1/7
7:20 am-5:40 pm
2 stops12h 20m
San Jose
Wed 1/14
2:25 pm-11:53 pm
1 stop7h 28m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Sat 1/17
7:20 am-5:40 pm
2 stops12h 20m
San Jose
Tue 1/20
9:15 am-11:53 pm
2 stops12h 38m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Sun 1/18
7:30 am-7:12 pm
2 stops13h 42m
San Jose
Fri 1/23
7:45 am-9:43 pm
2 stops11h 58m
| 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 November is currently the most expensive (average of $207). 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 55% 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 mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Crew
Boarding
Entertainment
Comfort
Overall
Food
Reviews
Walter,Aug 2025
OAK - SAN
Crew
Boarding
Entertainment
Comfort
Overall
Food
Reviews
Walter,Aug 2025
OAK - SAN
Crew
Boarding
Entertainment
Comfort
Overall
Food
Reviews
Walter,Aug 2025
OAK - SAN
Crew
Boarding
Entertainment
Comfort
Overall
Food
Reviews
Walter,Aug 2025
OAK - SAN
Crew
Boarding
Entertainment
Comfort
Overall
Food
Reviews
Walter,Aug 2025
OAK - SAN
Crew
Boarding
Entertainment
Comfort
Overall
Food
Reviews
Walter,Aug 2025
OAK - SAN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$80 | Average$222 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$142 | Average$201 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$189 | Average$384 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$262 | Average$361 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$338 | Average$496 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$348 | Average$496 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$352 | Average$620 | FlexibilityNo cancel fee | On-time71% |