At ORD, Garrett Popcorn near gate B8 is a must-try snack before your flight.
Round-trip from | $194 (Priceline) |
---|---|
One-way from | $55 (FlightHub) |
Popular in | July |
Cheapest in | October |
Average price | $371 |
Good round-trip deal | $331 or less |
Good one-way deal | $187 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Fri 9/19
6:00 am-11:30 am
1 stop7h 30m
San Jose
Mon 9/22
12:30 pm-11:59 pm
1 stop9h 29m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Thu 9/18
6:00 am-1:14 pm
1 stop9h 14m
San Jose
Tue 9/23
6:35 am-9:32 pm
1 stop12h 57m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Fri 9/26
6:00 am-11:30 am
1 stop7h 30m
San Jose
Mon 9/29
12:25 pm-11:59 pm
1 stop9h 34m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Fri 11/7
6:00 am-11:32 am
1 stop7h 32m
San Jose
Sun 11/9
4:51 pm-6:25 am
1 stop11h 34m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Thu 9/4
10:42 am-6:27 pm
2 stops9h 45m
San Jose
Mon 9/8
12:25 pm-11:59 pm
1 stop9h 34m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Fri 9/5
7:55 am-8:00 pm
2 stops14h 05m
San Jose
Sat 9/6
6:35 am-9:32 pm
1 stop12h 57m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Fri 9/5
6:00 am-11:30 am
1 stop7h 30m
San Jose
Mon 9/8
6:45 pm-10:40 am
2 stops13h 55m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Thu 9/18
6:00 am-1:14 pm
1 stop9h 14m
San Jose
Mon 9/22
6:45 pm-10:40 am
2 stops13h 55m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Thu 9/18
6:00 am-1:14 pm
1 stop9h 14m
San Jose
Mon 9/29
6:45 pm-10:40 am
2 stops13h 55m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Mon 9/15
6:00 am-11:30 am
1 stop7h 30m
San Jose
Mon 9/22
6:45 pm-10:40 am
2 stops13h 55m
The price you pay for your flight from Chicago to San Jose may vary depending on when you book. For the best chance of a lower fare, look to book 58 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Currently, September is the cheapest month in which you can book a flight from Chicago to San Jose (average of $255). Flying from Chicago to San Jose in June is currently the most expensive (average of $359). 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 Chicago to San Jose is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 17% on airfare.
Travelers seeking maximum savings on their Chicago to San Jose flight should consider departing on Wednesday at noon when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Denver (DEN) – chosen by Cheapflights users on 67% of 1-stop itineraries from Chicago to San Jose on Cheapflights.
Denver (DEN) is the most affordable 1-stop option, with an average round-trip price of $170.
Flights via Denver (DEN) have the shortest average one-way travel time for 1-stop routes: 10h 23m.
Flights via Denver (DEN) offer the fastest connection on this route, with an average layover time of 2h 58m.
Crew
Comfort
Food
Entertainment
Boarding
Overall
Reviews
Walter,Aug 2025
OAK - SAN
Crew
Comfort
Food
Entertainment
Boarding
Overall
Reviews
Walter,Aug 2025
OAK - SAN
Crew
Comfort
Food
Entertainment
Boarding
Overall
Reviews
Walter,Aug 2025
OAK - SAN
Crew
Comfort
Food
Entertainment
Boarding
Overall
Reviews
Walter,Aug 2025
OAK - SAN
Crew
Comfort
Food
Entertainment
Boarding
Overall
Reviews
Walter,Aug 2025
OAK - SAN
Crew
Comfort
Food
Entertainment
Boarding
Overall
Reviews
Walter,Aug 2025
OAK - SAN
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$90 | Average$248 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$124 | Average$228 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$277 | Average$382 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$350 | Average$477 | FlexibilityNo cancel fee | On-time63% | |
Cheapest$351 | Average$507 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$370 | Average$485 | FlexibilityNo cancel fee | On-time71% |