
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $268 (Southwest) |
One-way from | $113 (Kiwi.com) |
Popular in | February |
Cheapest in | January |
Average price | $456 |
Good round-trip deal | $407 or less |
Good one-way deal | $173 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Tue 9/15
6:05 am-11:36 am
1 stop7h 31m
San Jose
Tue 10/13
10:20 pm-9:52 am
1 stop9h 32m
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Tue 10/20
9:55 am-4:16 pm
2 stops8h 21m
San Jose
Mon 10/26
6:30 am-4:50 pm
1 stop8h 20m
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Thu 8/13
1:51 pm-8:24 pm
1 stop8h 33m
San Jose
Mon 8/17
6:59 am-6:33 pm
2 stops9h 34m
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Mon 9/14
9:49 am-5:13 pm
2 stops9h 24m
San Jose
Mon 10/12
8:05 pm-8:45 am
2 stops10h 40m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Tue 6/30
7:55 pm-10:40 pm
Nonstop4h 45m
San Jose
Thu 7/2
1:10 pm-12:45 am
1 stop9h 35m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Thu 7/9
7:59 pm-9:26 am
1 stop15h 27m
San Jose
Thu 7/16
8:00 am-5:00 am
1 stop19h 00m
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Wed 7/1
8:55 pm-11:25 pm
Nonstop4h 30m
San Jose
Tue 7/7
10:55 pm-5:00 am
Nonstop4h 05m
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Sat 6/20
12:15 pm-6:10 pm
1 stop7h 55m
San Jose
Wed 7/22
10:55 pm-5:00 am
Nonstop4h 05m
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Fri 7/10
9:54 am-6:26 pm
2 stops10h 32m
San Jose
Tue 7/14
10:00 pm-12:38 pm
2 stops12h 38m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Sun 7/19
7:29 am-2:12 pm
1 stop8h 43m
San Jose
Tue 7/21
8:25 pm-8:30 am
2 stops10h 05m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
Currently, October is the cheapest month in which you can book a flight from Chicago to San Jose, California (average of $80). Flying from Chicago to San Jose, California in March is currently the most expensive (average of $297). 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, California is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 22% on airfare.
The most flights from CHI to SJC are scheduled on a Tuesday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).
Booking 55 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to San Jose, California. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Comfort
Crew
Food
Entertainment
Boarding
Overall
Reviews
Walter,May 2026
LAS - BUR
Comfort
Crew
Food
Entertainment
Boarding
Overall
Reviews
Walter,May 2026
LAS - BUR
Comfort
Crew
Food
Entertainment
Boarding
Overall
Reviews
Walter,May 2026
LAS - BUR
Comfort
Crew
Food
Entertainment
Boarding
Overall
Reviews
Walter,May 2026
LAS - BUR
Comfort
Crew
Food
Entertainment
Boarding
Overall
Reviews
Walter,May 2026
LAS - BUR
Comfort
Crew
Food
Entertainment
Boarding
Overall
Reviews
Walter,May 2026
LAS - BUR
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$138 | Average$384 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$232 | Average$363 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$299 | Average$485 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$331 | Average$481 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$406 | Average$545 | FlexibilityNo cancel fee | On-time71% |