$85 Cheap flight deals from Chicago (CHI) to Pleasanton (SJC)
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This Weekend's Flight Deals from Chicago to Pleasanton
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Airfares from $85 One Way, $158 Round Trip from Chicago to Pleasanton
Prices starting at $158 for return flights and $85 for one-way flights to Pleasanton were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Pleasanton economy flight packages
Napa Valley Marriott Hotel & Spa
Dec 3 - Dec 6
Chicago (CHI) to Oakland (OAK)
Oakland (OAK) to Chicago (CHI)
Reviewed on Oct 26, 2026
Lavender, A Four Sisters Inn
Dec 3 - Dec 6
Chicago (CHI) to Oakland (OAK)
Oakland (OAK) to Chicago (CHI)
Reviewed on Oct 20, 2026
Milliken Creek Inn
Dec 3 - Dec 6
Chicago (CHI) to Oakland (OAK)
Oakland (OAK) to Chicago (CHI)
Reviewed on Oct 17, 2026
Pleasanton business class flight packages
Napa Valley Marriott Hotel & Spa
Dec 9 - Dec 12
Chicago (ORD) to Oakland (OAK)
Reviewed on Oct 26, 2026
Vino Bello Resort
Dec 9 - Dec 12
Chicago (ORD) to Oakland (OAK)
Reviewed on Oct 24, 2026
More About Flying To Pleasanton from Chicago
Route Information for Flights from Chicago to Pleasanton
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | SJC |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Pleasanton
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Pleasanton Airports
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.