SJC offers free Wi-Fi throughout the airport, perfect for catching up on work or entertainment before your flight.

Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $302 (Alaska Airlines) |
One-way from | $125 (Kiwi.com) |
Popular in | November |
Cheapest in | September |
Average price | $605 |
Good round-trip deal | $382 or less |
Good one-way deal | $224 or less |
Fly from
Fly to
Route
Depart
Return
Price
San JoseChicago
SJC - ORD
SJCORD
San Jose
Thu 12/11
11:40 am-11:59 pm
1 stop10h 19m
Chicago O'Hare Intl
Fri 12/12
2:14 pm-10:12 pm
1 stop9h 58m
San JoseChicago
SJC - ORD
SJCORD
San Jose
Mon 1/5
6:20 pm-9:40 am
2 stops13h 20m
Chicago O'Hare Intl
Wed 1/7
2:20 pm-10:55 pm
2 stops10h 35m
San JoseChicago
SJC - ORD
SJCORD
San Jose
Mon 2/2
7:15 am-9:42 pm
2 stops12h 27m
Chicago O'Hare Intl
Mon 2/16
7:40 am-4:54 pm
2 stops11h 14m
San JoseChicago
SJC - ORD
SJCORD
San Jose
Tue 12/16
9:04 am-11:59 pm
2 stops12h 55m
Chicago O'Hare Intl
Thu 12/25
2:15 pm-7:56 pm
1 stop7h 41m
San JoseChicago
SJC - ORD
SJCORD
San Jose
Mon 12/8
7:15 am-5:15 pm
1 stop8h 00m
Chicago O'Hare Intl
Thu 12/11
5:30 am-6:56 pm
2 stops15h 26m
San JoseChicago
SJC - ORD
SJCORD
San Jose
Sat 12/6
2:25 pm-11:59 pm
1 stop7h 34m
Chicago O'Hare Intl
Fri 12/12
6:00 am-3:54 pm
2 stops11h 54m
San JoseChicago
SJC - ORD
SJCORD
San Jose
Mon 12/8
4:35 pm-8:40 am
2 stops14h 05m
Chicago O'Hare Intl
Fri 12/12
7:50 am-3:54 pm
1 stop10h 04m
San JoseChicago
SJC - ORD
SJCORD
San Jose
Mon 12/8
9:04 am-11:59 pm
2 stops12h 55m
Chicago O'Hare Intl
Sun 12/14
7:50 am-3:54 pm
1 stop10h 04m
San JoseChicago
SJC - ORD
SJCORD
San Jose
Mon 12/8
11:40 am-11:59 pm
1 stop10h 19m
Chicago O'Hare Intl
Wed 12/10
6:00 am-3:54 pm
2 stops11h 54m
San JoseChicago
SJC - ORD
SJCORD
San Jose
Wed 12/3
9:04 am-11:59 pm
2 stops12h 55m
Chicago O'Hare Intl
Sun 12/7
7:50 am-3:54 pm
1 stop10h 04m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star |
Booking 6 days in advance of your planned departure date is, on average, the best time to get cheap flights from San Jose, California to Chicago O'Hare Intl Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Currently, December is the cheapest month in which you can book a flight from San Jose, California to Chicago O'Hare Intl Airport (average of $110). Flying from San Jose, California to Chicago O'Hare Intl Airport in November is currently the most expensive (average of $257). 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.
One of the essential ways to save on airfare from San Jose, California to Chicago O'Hare Intl Airport is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 54% on airfare.
Travelers seeking maximum savings on their San Jose, California to Chicago O'Hare Intl Airport flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Comfort
Entertainment
Boarding
Overall
Food
Crew
Reviews
Hannah,Aug 2025
SFO - SAN
Comfort
Entertainment
Boarding
Overall
Food
Crew
Reviews
Hannah,Aug 2025
SFO - SAN
Comfort
Entertainment
Boarding
Overall
Food
Crew
Reviews
Hannah,Aug 2025
SFO - SAN
Comfort
Entertainment
Boarding
Overall
Food
Crew
Reviews
Hannah,Aug 2025
SFO - SAN
Comfort
Entertainment
Boarding
Overall
Food
Crew
Reviews
Hannah,Aug 2025
SFO - SAN
Comfort
Entertainment
Boarding
Overall
Food
Crew
Reviews
Hannah,Aug 2025
SFO - SAN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$98 | Average$268 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$125 | Average$260 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$170 | Average$315 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$200 | Average$353 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$256 | Average$385 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$300 | Average$520 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$370 | Average$496 | FlexibilityNo cancel fee | On-time63% |