$58 Cheap flight deals from San Jose (SJC) to Chicago (CHI)
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This Weekend's Flight Deals from San Jose to Chicago
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 $58 One Way, $131 Round Trip from San Jose to Chicago
Prices starting at $131 for return flights and $58 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Chicago economy flight packages
Hotel Riu Plaza Chicago
Sep 20 - Sep 22
San Jose (SJC) to Chicago (ORD)
Chicago (ORD) to San Jose (SJC)
Reviewed on Jul 24, 2025
Trump International Hotel & Tower Chicago
Aug 30 - Sep 2
San Jose (SJC) to Chicago (ORD)
Chicago (ORD) to San Jose (SJC)
Reviewed on Jun 16, 2025
citizenM Chicago Downtown
Aug 30 - Sep 2
San Jose (SJC) to Chicago (ORD)
Chicago (ORD) to San Jose (SJC)
Reviewed on Jun 22, 2025
Chicago packages with premium economy flights
The Peninsula Chicago
Sep 18 - Sep 21
San Jose (SJC) to Chicago (ORD)
Reviewed on Feb 6, 2025
More About Flying To Chicago from San Jose
Route Information for Flights from San Jose to Chicago
Origin Airport IATA Code | SJC |
|---|---|
Destination Airport IATA Code | CHI |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
San Jose to Chicago
Orbitz is the best place to find guaranteed low prices on San Jose to Chicago flights. Because of our cutting-edge mobile tools and low fares on domestic and international flights, Orbitz is the best starting point for travelers.
Find Cheap San Jose to Chicago Flights
Orbitz offers free mobile apps for iPhone and Android devices—a great way to find fantastic deals on flights from San Jose to Chicago. Not only that, but you can check the status of your flight or even book low cost hotel rooms with the apps or on m.orbitz.com.
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Discount Travel Planning Made Simple
You will have no problems finding budget flights from San Jose to Chicago on Orbitz.com. If your travel plans are flexible, you can search for fares three days before and after a specific date to find the best price.
Frequently asked questions
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Flights from San Jose
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San Jose 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.