Cheap Flights from San Jose to Chicago

San Jose → Chicago
Any date
Find your flight
⇄
🌍 Anywhere
🇺🇸 United States €26
🇲🇽 Mexico €77
🇵🇦 Panama €101
🇨🇴 Colombia €98
🇩🇴 Dominican Republic €210
🇧🇷 Brazil €212
🇦🇷 Argentina €244
🇨🇷 Costa Rica €98
← Back Home› Deals› Chicago (25)
Chicago — United States
San Jose → Chicago
🇺🇸 United States · 25 flights from €118
22 Oct
06:00
WN · 4h
✈ Direct
€118
7 Oct
06:00
WN · 4h
✈ Direct
€118
16 Sep
06:00
WN · 4h
✈ Direct
€118
29 Sep
17:12
AS · 7h 9m
€124
9 Sep
15:29
AS · 8h 52m
€128
11 Sep
14:29
AS · 9h 52m
€128
24 Sep
20:38
F9 · 14h
€130
25 Sep
14:29
AS · 9h 52m
€148
€132
7 Sep
21:17
F9 · 26h 4m
€132
12 Nov
16:03
AS · 7h 34m
€135
2 Nov
17:39
AS · 7h 20m
€135
27 Oct
15:02
AS · 8h 18m
€135
25 Sep
02:35
WN · 7h 30m
€139
€137
30 Oct
16:15
AS · 7h 38m
€140
6 Oct
03:44
AS · 6h 56m
€141
2 Oct
14:29
AS · 9h 52m
€151
€143
23 Sep
17:12
AS · 7h 9m
€143
10 Sep
17:12
AS · 7h 9m
€150
€145
25 Sep
05:47
F9 · 23h 36m
€145
15 Sep
17:12
AS · 7h 9m
€147
14 Sep
17:12
AS · 7h 9m
€147
24 Sep
17:12
AS · 7h 9m
€152
8 Sep
03:14
F9 · 32h 3m
€156
9 Nov
07:00
WN · 4h
✈ Direct
€161
8 Sep
17:12
AS · 7h 9m
€209
With a stop
14 Sep
20:38
SJC → LAS → CHI
F9 + F9 · 8h layover in Las Vegas
€82
2 flights
12 Oct
21:15
SJC → LAS → CHI
F9 + F9 · 0d 23h stopover in Las Vegas
€114
2 flights
☕ 23h in Las Vegas — enough time to explore
29 Sep
21:25
SJC → LAS → CHI
AS + F9 · 1d 4h stopover in Las Vegas
€115
2 flights
☕ 28h in Las Vegas — enough time to explore
13 Oct
19:05
SJC → LAX → CHI
WN + F9 · 10h layover in Los Angeles
€116
2 flights
☕ 10h in Los Angeles — enough time to explore
13 Oct
04:16
SJC → LAS → CHI
F9 + F9 · 4h layover in Las Vegas
€117
2 flights
14 Oct
19:05
SJC → LAX → CHI
WN + F9 · 10h layover in Los Angeles
€119
2 flights
☕ 10h in Los Angeles — enough time to explore
12 Sep
21:25
SJC → LAS → CHI
AS + F9 · 5h layover in Las Vegas
€122
2 flights
17 Oct
20:05
SJC → LAX → CHI
WN + F9 · 9h layover in Los Angeles
€125
2 flights

You might also like

More from San Jose
Los Angeles
🔥 SUPER 1 stop↓76%
Los Angeles
SJC → LAX·Fri 18 Sep·1h 19m
F9
€107€26
Get offer
⭐ GREAT Direct↓69%
Las Vegas
SJC → LAS·Sun 6 Sep·1h 37m
F9
€34
Get offer
⭐ GREAT Direct↓22%
Las Vegas
SJC → LAS·Mon 14 Sep·1h 37m
F9
€36
Get offer
Los Angeles
⭐ GREAT Direct
Los Angeles
SJC → LAX·Mon 12 Oct·1h 23m
F9
€27
Get offer
Direct↓60%
Portland
SJC → PDX·Mon 14 Sep·1h 46m
AS
€86€48
Get offer
Direct↓55%
Long Beach
SJC → LGB·Sun 20 Sep·1h 25m
WN
€62
Get offer

Flight delayed or cancelled? You could be owed up to EUR 600 under EU261. Get your free claim letter →