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 | $270 (Alaska Airlines) |
One-way from | $96 (Kiwi.com) |
Popular in | June |
Cheapest in | September |
Average price | $460 |
Good round-trip deal | $417 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
Fri 1/9
2:20 pm-10:07 pm
1 stop9h 47m
San Jose
Sun 1/18
11:40 am-11:53 pm
1 stop10h 13m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Fri 1/9
6:06 pm-9:48 am
1 stop17h 42m
San Jose
Sun 1/11
9:05 am-5:10 pm
1 stop30h 05m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Thu 1/22
2:20 pm-10:07 pm
1 stop9h 47m
San Jose
Wed 1/28
9:15 am-11:53 pm
2 stops12h 38m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Fri 1/16
7:30 am-1:34 pm
1 stop8h 04m
San Jose
Tue 1/20
9:15 am-11:53 pm
2 stops12h 38m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Thu 12/18
7:50 am-3:54 pm
1 stop10h 04m
San Jose
Mon 3/9
7:00 am-11:53 pm
2 stops14h 53m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Tue 12/16
6:00 am-3:54 pm
2 stops11h 54m
San Jose
Tue 3/10
7:00 am-11:53 pm
2 stops14h 53m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Fri 1/16
3:44 pm-10:35 pm
1 stop8h 51m
San Jose
Tue 1/20
7:45 am-11:50 pm
2 stops14h 05m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Fri 2/20
1:00 pm-10:59 pm
1 stop11h 59m
San Jose
Sun 2/22
7:00 am-11:59 pm
1 stop14h 59m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Sun 12/14
5:51 pm-10:14 am
1 stop18h 23m
San Jose
Wed 1/7
12:46 pm-11:37 pm
1 stop8h 51m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Fri 1/16
2:20 pm-10:55 pm
2 stops10h 35m
San Jose
Sun 1/18
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 $204). 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 mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Overall
Entertainment
Boarding
Crew
Comfort
Food
Reviews
Walter,Aug 2025
OAK - SAN
Overall
Entertainment
Boarding
Crew
Comfort
Food
Reviews
Walter,Aug 2025
OAK - SAN
Overall
Entertainment
Boarding
Crew
Comfort
Food
Reviews
Walter,Aug 2025
OAK - SAN
Overall
Entertainment
Boarding
Crew
Comfort
Food
Reviews
Walter,Aug 2025
OAK - SAN
Overall
Entertainment
Boarding
Crew
Comfort
Food
Reviews
Walter,Aug 2025
OAK - SAN
Overall
Entertainment
Boarding
Crew
Comfort
Food
Reviews
Walter,Aug 2025
OAK - SAN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$80 | Average$244 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$142 | Average$213 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$262 | Average$361 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$265 | Average$386 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$339 | Average$504 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$348 | Average$496 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$352 | Average$620 | FlexibilityNo cancel fee | On-time71% |