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 | $243 (Kiwi.com) |
One-way from | $81 (CheapOair) |
Popular in | November |
Cheapest in | September |
Average price | $448 |
Good round-trip deal | $397 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
vie. 1/23
6:06 pm-9:48 am
1 stop17h 42m
San Jose
mié. 1/28
12:46 pm-11:37 pm
1 stop8h 51m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
jue. 1/8
8:00 am-2:42 pm
1 stop8h 42m
San Jose
mar. 1/13
7:52 pm-11:37 pm
1 stop25h 45m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
sáb. 1/24
8:00 am-8:04 pm
1 stop14h 04m
San Jose
dom. 1/25
6:15 am-5:10 pm
1 stop8h 55m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
mié. 1/7
8:00 am-9:48 am
1 stop27h 48m
San Jose
lun. 1/12
6:02 pm-11:50 pm
1 stop27h 48m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
mié. 1/7
6:06 pm-1:00 pm
1 stop20h 54m
San Jose
sáb. 1/10
12:46 pm-11:37 pm
1 stop8h 51m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
mié. 1/14
3:35 pm-9:48 am
1 stop20h 13m
San Jose
dom. 1/18
7:00 am-11:37 pm
1 stop14h 37m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
mié. 1/7
8:00 am-9:48 am
1 stop27h 48m
San Jose
dom. 1/11
12:46 pm-11:37 pm
1 stop8h 51m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
jue. 1/15
3:44 pm-10:35 pm
1 stop8h 51m
San Jose
mié. 1/21
11:00 am-11:50 pm
1 stop10h 50m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
dom. 1/18
7:30 am-1:34 pm
1 stop8h 04m
San Jose
mar. 1/27
2:25 pm-11:53 pm
1 stop7h 28m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
mié. 1/14
2:18 pm-10:29 am
2 stops22h 11m
San Jose
dom. 1/18
11:14 am-9:11 pm
1 stop7h 57m
| 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 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.
Comfort
Crew
Overall
Entertainment
Food
Boarding
Reviews
Walter,Aug 2025
OAK - SAN
Comfort
Crew
Overall
Entertainment
Food
Boarding
Reviews
Walter,Aug 2025
OAK - SAN
Comfort
Crew
Overall
Entertainment
Food
Boarding
Reviews
Walter,Aug 2025
OAK - SAN
Comfort
Crew
Overall
Entertainment
Food
Boarding
Reviews
Walter,Aug 2025
OAK - SAN
Comfort
Crew
Overall
Entertainment
Food
Boarding
Reviews
Walter,Aug 2025
OAK - SAN
Comfort
Crew
Overall
Entertainment
Food
Boarding
Reviews
Walter,Aug 2025
OAK - SAN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$80 | Average$244 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$142 | Average$215 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$262 | Average$361 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$265 | Average$391 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$338 | Average$500 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$348 | Average$506 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$352 | Average$620 | FlexibilityNo cancel fee | On-time71% |