
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $282 (Delta) |
One-way from | $144 (Delta) |
Popular in | March |
Cheapest in | February |
Average price | $486 |
Good round-trip deal | $471 or less |
Good one-way deal | $203 or less |
Fly from
Fly to
Route
Depart
Return
San JoseChicago
SJC - ORD
SJCORD
San Jose
Tue 6/23
9:54 am-9:57 pm
2 stops10h 03m
Chicago O'Hare Intl
Wed 6/24
8:36 am-5:17 pm
2 stops10h 41m
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Mon 6/22
10:55 pm-5:00 am
Nonstop4h 05m
Chicago Midway
Wed 7/1
8:55 pm-11:25 pm
Nonstop4h 30m
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Wed 6/10
7:35 pm-4:40 am
1 stop7h 05m
Chicago Midway
Tue 6/16
5:25 am-11:25 am
2 stops8h 00m
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Tue 6/16
8:55 pm-5:25 am
1 stop6h 30m
Chicago Midway
Tue 6/23
5:50 pm-11:00 pm
2 stops7h 10m
San JoseChicago
SJC - ORD
SJCORD
San Jose
Tue 6/16
9:54 am-9:57 pm
2 stops10h 03m
Chicago O'Hare Intl
Sat 6/20
7:45 am-12:38 pm
1 stop6h 53m
San JoseChicago
SJC - ORD
SJCORD
San Jose
Thu 6/11
7:13 am-11:36 pm
1 stop14h 23m
Chicago O'Hare Intl
Wed 7/1
6:20 am-11:24 am
1 stop7h 04m
San JoseChicago
SJC - ORD
SJCORD
San Jose
Fri 7/17
2:59 pm-11:18 pm
1 stop6h 19m
Chicago O'Hare Intl
Sun 7/19
6:30 am-3:46 pm
2 stops11h 16m
San JoseChicago
SJC - RFD
SJCRFD
San Jose
Thu 9/24
9:10 am-8:39 pm
1 stop9h 29m
Chicago Greater Rockford
Sun 9/27
9:29 pm-1:29 pm
1 stop18h 00m
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Fri 7/17
8:19 pm-8:37 am
2 stops10h 18m
Chicago Midway
Mon 7/20
9:19 am-5:12 pm
2 stops9h 53m
San JoseChicago
SJC - ORD
SJCORD
San Jose
Sat 6/6
11:41 am-12:08 am
2 stops10h 27m
Chicago O'Hare Intl
Tue 6/9
6:30 am-3:53 pm
2 stops11h 23m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
Currently, March is the cheapest month in which you can book a flight from San Jose, California to Chicago (average of $95). Flying from San Jose, California to Chicago in April is currently the most expensive (average of $265). 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, California to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 18% on your trip compared to booking a flight in the evening.
The most flights from SJC to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).
The best time to book flights from San Jose, California to Chicago is 88 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.
Crew
Food
Entertainment
Overall
Boarding
Comfort
Reviews
Franzi,Mar 2026
SFO - PDX
Crew
Food
Entertainment
Overall
Boarding
Comfort
Reviews
Franzi,Mar 2026
SFO - PDX
Crew
Food
Entertainment
Overall
Boarding
Comfort
Reviews
Franzi,Mar 2026
SFO - PDX
Crew
Food
Entertainment
Overall
Boarding
Comfort
Reviews
Franzi,Mar 2026
SFO - PDX
Crew
Food
Entertainment
Overall
Boarding
Comfort
Reviews
Franzi,Mar 2026
SFO - PDX
Crew
Food
Entertainment
Overall
Boarding
Comfort
Reviews
Franzi,Mar 2026
SFO - PDX
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$121 | Average$239 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$131 | Average$294 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$200 | Average$424 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$235 | Average$339 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$236 | Average$378 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$270 | Average$517 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$278 | Average$554 | FlexibilityNo cancel fee | On-time69% |