Book United San Jose, CA to Chicago flight deals from $397

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Cruise ships and tour boats docked by a ferris wheel and urban buildings at Navy Pier in Chicago

Plan ahead for flights from San Jose, CA to Chicago

from
to
Type
Dates
Price*
San Jose, CA (SJC)
to Chicago (ORD)
Roundtrip
Depart Mon 16 Jul 2018
Return Tue 31 Jul 2018
from$ 397*Viewed: 6 hours ago
San Jose, CA (SJC)
to Chicago (ORD)
Roundtrip
Depart Tue 17 Jul 2018
Return Wed 1 Aug 2018
from$ 397*Viewed: 6 hours ago
San Jose, CA (SJC)
to Chicago (ORD)
Roundtrip
Depart Wed 18 Jul 2018
Return Thu 2 Aug 2018
from$ 397*Viewed: 6 hours ago
San Jose, CA (SJC)
to Chicago (ORD)
Roundtrip
Depart Thu 19 Jul 2018
Return Fri 3 Aug 2018
from$ 397*Viewed: 6 hours ago
San Jose, CA (SJC)
to Chicago (ORD)
Roundtrip
Depart Fri 20 Jul 2018
Return Sat 4 Aug 2018
from$ 397*Viewed: 6 hours ago
San Jose, CA (SJC)
to Chicago (ORD)
Roundtrip
Depart Sun 22 Jul 2018
Return Mon 6 Aug 2018
from$ 397*Viewed: 6 hours ago
San Jose, CA (SJC)
to Chicago (ORD)
Roundtrip
Depart Sun 8 Jul 2018
Return Mon 23 Jul 2018
from$ 422*Viewed: 6 hours ago
San Jose, CA (SJC)
to Chicago (ORD)
Roundtrip
Depart Mon 9 Jul 2018
Return Tue 24 Jul 2018
from$ 422*Viewed: 6 hours ago
San Jose, CA (SJC)
to Chicago (ORD)
Roundtrip
Depart Tue 10 Jul 2018
Return Wed 25 Jul 2018
from$ 422*Viewed: 6 hours ago
San Jose, CA (SJC)
to Chicago (ORD)
Roundtrip
Depart Wed 11 Jul 2018
Return Thu 26 Jul 2018
from$ 422*Viewed: 6 hours ago
*Prices have been available for round trips within the last 48 hours and may not be currently available. Fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply.

Weather in Chicago

71 °FSaturday06/23/2018
68 °FSunday06/24/2018
70 °FMonday06/25/2018
76 °FTuesday06/26/2018
85 °FWednesday06/27/2018
87 °FThursday06/28/2018
90 °FFriday06/29/2018
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