Cheap Flights from San Jose to Chicago

San Jose → Chicago

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🇺🇸 United States €42

🇨🇴 Colombia €104

🇵🇦 Panama €99

🇲🇽 Mexico €104

🇵🇷 Puerto Rico €178

🇦🇷 Argentina €235

🇧🇷 Brazil €227

🇨🇦 Canada €194

← Back Home› Deals› Chicago (17)

San Jose → Chicago

🇺🇸 United States · 17 flights from €123

Cheapest Soonest

With a stop

WN + F9 · 0d 12h stopover in Los Angeles

€184

2 flights

☕ 12h in Los Angeles — enough time to explore

5 Aug

17:03

SJC → PHX → CHI

AS + UA · 1d 0h stopover in Phoenix

€191

2 flights

☕ 24h in Phoenix — enough time to explore

28 Jul

14:13

SJC → WAS → CHI

AS + UA · 3h layover in Washington

AS + AA · 5h layover in New York

AS + AA · 1d 6h stopover in New York

€229

2 flights

☕ 30h in New York — enough time to explore

29 Jun

21:12

SJC → DEN → CHI

F9 + F9 · 0d 13h stopover in Denver

€243

2 flights

☕ 13h in Denver — enough time to explore

11 Jul

01:37

SJC → NYC → CHI

UA + AA · 8h layover in New York

AS + AA · 1d 6h stopover in New York

€259

2 flights

☕ 30h in New York — enough time to explore

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