Find Deals on Flights from San Jose to Chicago (SJC - CHI)

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
Students
under 26
The price shown for each flight will be the average for all passengers including any infants.
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Book cheap flights from San Jose to Chicago

(Round-trip)
Depart: Tue Dec 13 2016 Return: Wed Dec 14 2016 Trip spans 2 days
Major Airline
Major Airline
SJC
MDW
1h 39m
nonstop
MDW
SJC
5h 39m
nonstop
Depart: Sun Jan 8 2017 Return: Tue Jan 17 2017 Trip spans 10 days
American Airlines
American Airlines
SJC
ORD
4h 14m
nonstop
ORD
SJC
4h 38m
nonstop
Depart: Mon Feb 6 2017 Return: Mon Feb 13 2017 Trip spans 8 days
Southwest
Southwest
SJC
MDW
4h 05m
nonstop
MDW
SJC
4h 45m
nonstop
Depart: Thu Jan 12 2017 Return: Fri Jan 13 2017 Trip spans 2 days
Delta
Delta
SJC
MDW
8h 24m
1 stop
MDW
SJC
7h 10m
1 stop
Depart: Sat Apr 8 2017 Return: Tue Apr 11 2017 Trip spans 4 days
Alaska Airlines
Alaska Airlines
SJC
ORD
8h 34m
1 stop
ORD
SJC
8h 11m
1 stop
Depart: Thu Jan 12 2017 Return: Sun Jan 15 2017 Trip spans 4 days
Major Airline
Major Airline
SJC
MDW
1h 39m
nonstop
MDW
SJC
5h 39m
nonstop
Depart: Thu Jan 12 2017 Return: Sun Jan 15 2017 Trip spans 4 days
American Airlines
American Airlines
SJC
ORD
4h 15m
nonstop
ORD
SJC
4h 38m
nonstop
Depart: Tue Dec 6 2016 Return: Thu Dec 8 2016 Trip spans 3 days
Major Airline
Major Airline
SJC
ORD
8h 41m
1 stop
ORD
SJC
10h 51m
1 stop
Depart: Fri Feb 3 2017 Return: Mon Feb 6 2017 Trip spans 4 days
Delta
Delta
SJC
MDW
6h 29m
1 stop
MDW
SJC
7h 10m
1 stop
Depart: Wed Feb 1 2017 Return: Thu Feb 2 2017 Trip spans 2 days
American Airlines
American Airlines
SJC
ORD
4h 15m
nonstop
ORD
SJC
4h 38m
nonstop
Depart: Tue Apr 25 2017 Return: Thu May 4 2017 Trip spans 10 days
Delta
Delta
SJC
MDW
6h 23m
1 stop
MDW
SJC
7h 03m
1 stop
Depart: Wed Jan 25 2017 Return: Tue Jan 31 2017 Trip spans 7 days
Major Airline
Major Airline
SJC
ORD
8h 14m
1 stop
ORD
SJC
10h 50m
1 stop
Depart: Sat Feb 4 2017 Return: Sun Feb 5 2017 Trip spans 2 days
American Airlines
American Airlines
SJC
ORD
4h 15m
nonstop
ORD
SJC
4h 38m
nonstop
Depart: Thu Feb 9 2017 Return: Sun Feb 12 2017 Trip spans 4 days
American Airlines
American Airlines
SJC
ORD
4h 15m
nonstop
ORD
SJC
4h 38m
nonstop
Depart: Wed Dec 14 2016 Return: Thu Dec 15 2016 Trip spans 2 days
Delta
Delta
SJC
MDW
6h 20m
1 stop
MDW
SJC
6h 50m
1 stop
Depart: Sun Mar 5 2017 Return: Thu Mar 9 2017 Trip spans 5 days
American Airlines
American Airlines
SJC
ORD
4h 16m
nonstop
ORD
SJC
4h 35m
nonstop
Depart: Thu Jan 5 2017 Return: Mon Jan 9 2017 Trip spans 5 days
Delta
Delta
SJC
ORD
8h 33m
2 stops
ORD
SJC
6h 42m
1 stop
Depart: Thu May 4 2017 Return: Mon May 8 2017 Trip spans 5 days
American Airlines
American Airlines
SJC
ORD
4h 16m
nonstop
ORD
SJC
4h 35m
nonstop
Depart: Thu Jan 5 2017 Return: Mon Jan 9 2017 Trip spans 5 days
Delta
Delta
SJC
MDW
8h 17m
1 stop
MDW
SJC
9h 42m
2 stops
Depart: Tue Mar 28 2017 Return: Sun Apr 2 2017 Trip spans 6 days
Major Airline
Major Airline
SJC
MDW
1h 39m
1 stop
MDW
SJC
5h 39m
1 stop
Direct flights SJC to CHI on American Airlines
Flight # Depart SJC Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
1628 6:20 am 12:43 pm Dec 18 - Jan 8
1628 8:00 am 2:17 pm Jan 4 - Jan 4
1628 8:00 am 2:17 pm Dec 15 - Jan 3
1092 1:10 pm 7:24 pm Dec 8 - Dec 14
1092 1:13 pm 7:28 pm Jan 9 - Jan 10
1524 1:15 pm 7:29 pm Dec 18 - Dec 18
1524 1:15 pm 7:29 pm Jan 1 - Jan 8
1524 1:15 pm 7:29 pm Jan 7 - Jan 7
1524 1:15 pm 7:29 pm Dec 15 - Jan 2
1629 10:30 pm 4:44 am Dec 15 - Dec 30
1629 10:30 pm 4:44 am Jan 1 - Jan 2
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Airports
Origin

San Jose
$290
Destination

Chicago
only $295
only $290
Airlines Airline reviews

11 travelers who booked a flight from San Jose to Chicago rated their chosen airlines with an average of 8.0.

Overall
8.2
Boarding
8.4
Crew
8.4
Comfort
8.2
Food
6.5
Entertainment
7.6