SJC offers free Wi-Fi throughout the airport, making it easy to stay connected before your flight.
Round-trip from | $254 (Cheapflightsfares) |
---|---|
One-way from | $108 (Mytrip) |
Popular in | December |
Cheapest in | January |
Average price | $413 |
Good round-trip deal | $387 or less |
Good one-way deal | $185 or less |
Fly from
Fly to
Route
Depart
Return
Price
San JoseChicago
SJC - ORD
SJCORD
San Jose
Sun 7/27
6:30 am-2:13 pm
1 stop5h 43m
Chicago O'Hare Intl
Sat 8/9
7:49 pm-11:54 pm
1 stop6h 05m
San JoseChicago
SJC - ORD
SJCORD
San Jose
Thu 7/24
6:30 am-2:13 pm
1 stop5h 43m
Chicago O'Hare Intl
Sun 7/27
9:56 pm-1:17 pm
1 stop17h 21m
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Wed 8/27
6:25 am-5:37 pm
1 stop9h 12m
Chicago Midway
Tue 9/2
1:08 pm-8:42 pm
1 stop9h 34m
San JoseChicago
SJC - ORD
SJCORD
San Jose
Tue 8/5
6:00 am-3:05 pm
1 stop7h 05m
Chicago O'Hare Intl
Tue 8/5
4:39 pm-10:59 pm
1 stop8h 20m
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Thu 7/24
12:18 pm-8:54 pm
1 stop6h 36m
Chicago Midway
Thu 8/7
8:38 pm-1:17 pm
2 stops18h 39m
San JoseChicago
SJC - ORD
SJCORD
San Jose
Fri 8/22
6:00 pm-8:24 am
2 stops12h 24m
Chicago O'Hare Intl
Sun 8/24
5:45 am-1:00 pm
2 stops9h 15m
San JoseChicago
SJC - RFD
SJCRFD
San Jose
Thu 9/18
8:15 am-6:52 pm
1 stop8h 37m
Chicago Greater Rockford
Mon 9/22
10:37 am-9:49 pm
2 stops13h 12m
San JoseChicago
SJC - ORD
SJCORD
San Jose
Thu 8/21
12:22 pm-12:32 am
1 stop10h 10m
Chicago O'Hare Intl
Fri 8/22
6:00 am-5:32 pm
2 stops13h 32m
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Thu 9/25
11:30 am-7:40 pm
1 stop6h 10m
Chicago Midway
Mon 9/29
7:55 pm-10:25 pm
Nonstop4h 30m
San JoseChicago
SJC - ORD
SJCORD
San Jose
Wed 8/20
6:00 am-5:40 am
2 stops21h 40m
The best time to book flights from San Jose to Chicago is 81 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Currently, August is the cheapest month in which you can book a flight from San Jose to Chicago (average of $245). Flying from San Jose to Chicago in March is currently the most expensive (average of $321). 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.
A simple way to save on the total cost of your ticket is to fly from San Jose to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 32% on your trip compared to booking a flight in the evening.
Travelers seeking maximum savings on their San Jose to Chicago flight should consider departing on Monday 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.
Boarding
Crew
Overall
Entertainment
Comfort
Food
Reviews
James,Apr 2025
LAX - SFO
Boarding
Crew
Overall
Entertainment
Comfort
Food
Reviews
James,Apr 2025
LAX - SFO
Boarding
Crew
Overall
Entertainment
Comfort
Food
Reviews
James,Apr 2025
LAX - SFO
Boarding
Crew
Overall
Entertainment
Comfort
Food
Reviews
James,Apr 2025
LAX - SFO
Boarding
Crew
Overall
Entertainment
Comfort
Food
Reviews
James,Apr 2025
LAX - SFO
Boarding
Crew
Overall
Entertainment
Comfort
Food
Reviews
James,Apr 2025
LAX - SFO
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$98 | Average$259 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$108 | Average$253 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$170 | Average$243 | FlexibilityNo cancel fee | On-time75% | |
Cheapest$200 | Average$494 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$236 | Average$352 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$287 | Average$495 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$358 | Average$491 | FlexibilityNo cancel fee | On-time63% |