Title: CA $134 Cheap Flights from San Jose (SJC) to Chicago (CHI) - Expedia.ca ![City of Chicago. Image of Chicago downtown and Chicago River with bridges at sunny summer day](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # CA $134 Cheap Flights from San Jose (SJC) to Chicago (CHI) [View CA $134 flight on Tue, Jan 6, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:SJC,to:ORD,departure:06/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:134.00&airProductToken=AQpuCjUIxJgBEgQzNzM2GLISIJIBKJfegQMwp9-BAzhFQABYAWoJTUFJTkJBU0lDcghWQVZXSDNCQwo1CMSYARIEMjEwOBiSASCuHCiJ4YEDMPjigQM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0gzQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travellers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Flight 1 Leaving from Going to Departing Flight 2 Leaving from Going to Departing ## Popular airlines from Norman Y. Mineta San Jose Intl. Airport (SJC) to Chicago - ![Alaska Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:sjc,to:chi,departure:09/11/2025TANYT&leg2=from:chi,to:sjc,departure:16/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![Southwest Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:sjc,to:chi,departure:09/11/2025TANYT&leg2=from:chi,to:sjc,departure:16/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![Delta](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.ca/Flights-Search?leg1=from:sjc,to:chi,departure:09/11/2025TANYT&leg2=from:chi,to:sjc,departure:16/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![American Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:sjc,to:chi,departure:09/11/2025TANYT&leg2=from:chi,to:sjc,departure:16/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![United](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.ca/Flights-Search?leg1=from:sjc,to:chi,departure:09/11/2025TANYT&leg2=from:chi,to:sjc,departure:16/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![Frontier Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:sjc,to:chi,departure:09/11/2025TANYT&leg2=from:chi,to:sjc,departure:16/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![Hawaiian Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_HA.svg) Hawaiian Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:sjc,to:chi,departure:09/11/2025TANYT&leg2=from:chi,to:sjc,departure:16/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"HA"}}]) ![notification illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 30% on select hotels after you book a flight\* ![trophy illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.ca/login) ## Cheap flights from San Jose (SJC) to Chicago (CHI) Prices were available within the past 7 days and start at CA $134 for one-way flights and CA $293 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Jan 15 - Tue, Jan 20 SJC San Jose ORD Chicago CA $293 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:15/01/2026TANYT&leg2=from:ORD,to:SJC,departure:20/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:292.70&airProductToken=AQpuCjUIxJgBEgQzNzM2GLISIJIBKLfDggMwx8SCAzhFQABYAWoJTUFJTkJBU0lDcghYQVZXQjRCQwo1CMSYARIEMjEwOBiSASCuHCipxoIDMJjIggM4RUABWAFqCU1BSU5CQVNJQ3IIWEFWU0E1QkMKbgo1CMSYARIEMjA0MRiuHCCSASjq-IIDMIf7ggM4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0gzQkMKNQjEmAESBDM3ODkYkgEgshIow_uCAzDR_IIDOEVAAVgBaglNQUlOQkFTSUNyCFZBVldIM0JDEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Jan 15 - Tue, Jan 20 SJC San Jose ORD Chicago CA $302 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:15/01/2026TANYT&leg2=from:ORD,to:SJC,departure:20/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:301.33&airProductToken=AQpuCjUIxJgBEgQzNzM2GLISIJIBKLfDggMwx8SCAzhFQABYAWoJTUFJTkJBU0lDcghYQVZXQjRCQwo1CMSYARIEMjEwOBiSASCuHCipxoIDMJjIggM4RUABWAFqCU1BSU5CQVNJQ3IIWEFWU0E1QkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Jan 15 - Tue, Jan 20 SJC San Jose ORD Chicago CA $303 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:15/01/2026TANYT&leg2=from:ORD,to:SJC,departure:20/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:302.44&airProductToken=AQpoCjIIwYIBEgQzODM4GLISIO-5ASjSwoIDMMTDggM4QkAAWAFqBUJBU0lDcghPVkFIWlNCVgoyCMGCARIEMjU0MRjvuQEgrhwo5MOCAzC7xYIDOEJAAVgBagVCQVNJQ3IIT1ZBSFpTQlYSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Jan 15 - Tue, Jan 20 SJC San Jose ORD Chicago CA $309 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:15/01/2026TANYT&leg2=from:ORD,to:SJC,departure:20/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:309.00&airProductToken=AQpoCjIIwYIBEgQzODM4GLISIO-5ASjSwoIDMMTDggM4QkAAWAFqBUJBU0lDcghPVkFIWlNCVgoyCMGCARIEMjU0MRjvuQEgrhwo5MOCAzC7xYIDOEJAAVgBagVCQVNJQ3IIT1ZBSFpTQlYSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Thu, Jan 15 - Tue, Jan 20 SJC San Jose ORD Chicago CA $319 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:15/01/2026TANYT&leg2=from:ORD,to:SJC,departure:20/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:318.69&airProductToken=AQpgCi4IwaYBEgQyMjE5GLISIJJoKIPFggMw2MWCAzhYQABYAWoCU1ZyCE9IMk9RVkJOCi4IwaYBEgQxNDkzGJJoIK4cKIbGggMwkciCAzhYQAFYAWoCU1ZyCE9IMk9BVUJOEgoIAhABGAIqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Jan 15 - Tue, Jan 20 SJC San Jose ORD Chicago CA $321 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:15/01/2026TANYT&leg2=from:ORD,to:SJC,departure:20/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:320.03&airProductToken=AQpuCjUIxJgBEgQzNzM2GLISIJIBKLfDggMwx8SCAzhFQABYAWoJTUFJTkJBU0lDcghYQVZXQjRCQwo1CMSYARIEMjEwOBiSASCuHCipxoIDMJjIggM4RUABWAFqCU1BSU5CQVNJQ3IIWEFWU0E1QkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Thu, Jan 15 - Tue, Jan 20 SJC San Jose ORD Chicago CA $323 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:15/01/2026TANYT&leg2=from:ORD,to:SJC,departure:20/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:322.80&airProductToken=AQpgCi4IwaYBEgQyMjE5GLISIJJoKIPFggMw2MWCAzhYQABYAWoCU1ZyCE9IMk9RVkJOCi4IwaYBEgQxNDkzGJJoIK4cKIbGggMwkciCAzhYQAFYAWoCU1ZyCE9IMk9BVUJOCmAKLgjBpgESBDE0NDcYrhwgkmgoxfyCAzDf_oIDOFhAAFgBagJTVnIIR0gyT1hKQk4KLgjBpgESBDIxODMYkmggshIoi4CDAzDrgIMDOFhAAVgBagJTVnIIR0gyT1hKQk4SCggCEAEYAioCQVMYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Jan 15 - Tue, Jan 20 SJC San Jose ORD Chicago CA $327 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:15/01/2026TANYT&leg2=from:ORD,to:SJC,departure:20/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:326.26&airProductToken=AQpuCjUIxJgBEgQzNzM2GLISIJIBKLfDggMwx8SCAzhFQABYAWoJTUFJTkJBU0lDcghYQVZXQjRCQwo1CMSYARIEMjEwOBiSASCuHCipxoIDMJjIggM4RUABWAFqCU1BSU5CQVNJQ3IIWEFWU0E1QkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Jan 15 - Tue, Jan 20 SJC San Jose ORD Chicago CA $328 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:15/01/2026TANYT&leg2=from:ORD,to:SJC,departure:20/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:327.70&airProductToken=AQpoCjIIwYIBEgQzODM4GLISIO-5ASjSwoIDMMTDggM4QkAAWAFqBUJBU0lDcghPVkFIWlNCVgoyCMGCARIEMjU0MRjvuQEgrhwo5MOCAzC7xYIDOEJAAVgBagVCQVNJQ3IIT1ZBSFpTQlYSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![Hawaiian Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/HA.gif) Thu, Oct 30 - Tue, Nov 4 SJC San Jose ORD Chicago CA $608 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:30/10/2025TANYT&leg2=from:ORD,to:SJC,departure:04/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:607.70&airProductToken=AQpECiAIyIIBEgQ3MDU3GLISIJJoKNnk-wIwreX7AjhVQABYAQogCMiCARIENjUzNRiSaCCuHCik6vsCMI7s-wI4VUABWAEKRAogCMiCARIENzQ0NxiuHCCSaCiGmvwCMI-c_AI4VUAAWAEKIAjIggESBDY1NDkYkmggshIo6538AjDNnvwCOFVAAVgBEgoIARABGAEqAkhBGAEiBAgBEAEoBDAB) ## Find the cheapest month to fly from San Jose (SJC) to Chicago (CHI) ### February is typically the cheapest month to fly From CA $151 - CA $531 per traveller. Flight from San Jose to Chicago (SJC - ORD) route information | Origin airport | Norman Y. Mineta San Jose Intl. | | --- | --- | | Destination airport | O'Hare Intl. | | Roundtrip price | CA $293 | | Distance | 2919 km | ## San Jose to Illinois Flights **The easy way to book your flights from San Jose to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from San Jose whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to CHI-All Airports, too.   Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from San Jose to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Norman Y. Mineta San Jose Intl., SJC to CHI-All Airports, CHI**  Sort your search results by price to find great deals on your flight from San Jose to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from San Jose currently is just CA $293 rising to CA $608.   Here are more money-saving tips:  - Fly in January when flight prices are normally at their lowest  - Book about a month to 6 weeks before you travel for the best prices to Chicago   - Avoid peak season and weekends when flights can cost more - Early morning and late-night flights are sometimes cheaper, so try varying your travel times  - One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free!  **Reasons to choose Expedia for your flight to Chicago from San Jose**  Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today. ## Explore a world of travel with Expedia \*Available to Expedia members.