$135 Cheap flight deals from Chicago (CHI) to Watsonville (SJC)
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This Weekend's Flight Deals from Chicago to Watsonville
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 $135 One Way, $247 Round Trip from Chicago to Watsonville
Prices starting at $247 for return flights and $135 for one-way flights to Watsonville were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Watsonville economy flight packages
Days Inn & Suites by Wyndham Mountain View
Nov 1 - Nov 3
Chicago (ORD) to San Jose (SJC)
San Jose (SJC) to Chicago (ORD)
Reviewed on Sep 26, 2026
Holiday Inn San Jose - Silicon Valley by IHG
Nov 1 - Nov 3
Chicago (ORD) to San Jose (SJC)
San Jose (SJC) to Chicago (ORD)
Hilton Garden Inn San Jose/Milpitas
Nov 1 - Nov 3
Chicago (ORD) to San Jose (SJC)
San Jose (SJC) to Chicago (ORD)
Reviewed on Sep 25, 2026
More About Flying To Watsonville from Chicago
Route Information for Flights from Chicago to Watsonville
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | SJC |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Watsonville
Whether you want to book cheap flights from Chicago to Watsonville or are looking for the perfect package holiday, Orbitz is your one-stop source. Taking the stress and expense out of travel, Orbitz helps you find the best fares for Chicago to Watsonville flights.
Make the Most of Your Vacation
Not only does Orbitz have cheap deals for Chicago to Watsonville flights, we can also help you plan your vacation in advance. Why wait in lengthy lines for tickets to shows, amusement parks, and other attractions when you could be making the most of your holiday? Add activities to your flight booking for fewer hassles once you arrive in Watsonville.
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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.