Title: CA $185 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 $185 Cheap Flights from San Jose (SJC) to Chicago (CHI) [View CA $185 flight on Sat, Jan 10, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:SJC,to:ORD,departure:10/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:184.50&airProductToken=AQpgCi4IwaYBEgQyNDkyGLISIJJoKN6LggMws4yCAzhYQABYAWoCU1ZyCE9IMk9YVkJOCi4IwaYBEgQxNDkzGJJoIK4cKOaNggMw8Y-CAzhYQAFYAWoCU1ZyCEdIMk9YVkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travellers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Leaving from Going to Departing Returning Add a place to stay Add a car Direct flights only ## 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:16/12/2025TANYT&leg2=from:CHI,to:SJC,departure:23/12/2025TANYT&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:16/12/2025TANYT&leg2=from:CHI,to:SJC,departure:23/12/2025TANYT&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:16/12/2025TANYT&leg2=from:CHI,to:SJC,departure:23/12/2025TANYT&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:16/12/2025TANYT&leg2=from:CHI,to:SJC,departure:23/12/2025TANYT&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:16/12/2025TANYT&leg2=from:CHI,to:SJC,departure:23/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![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:16/12/2025TANYT&leg2=from:CHI,to:SJC,departure:23/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"HA"}}]) - ![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:16/12/2025TANYT&leg2=from:CHI,to:SJC,departure:23/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![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 $185 for one-way flights and CA $337 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, Feb 7 - Sat, Feb 14 SJC San Jose ORD Chicago CA $337 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:07/02/2026TANYT&leg2=from:ORD,to:SJC,departure:14/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:336.80&airProductToken=AQpgCi4IwaYBEgQyNDkyGLISIJJoKN7GhAMws8eEAzhYQABYAWoCU1ZyCEdIMk9YVUJOCi4IwaYBEgQxNDkzGJJoIK4cKObIhAMw8cqEAzhYQAFYAWoCU1ZyCEdIMk9YVkJOCmAKLgjBpgESBDE0NDcYrhwgkmgo05WFAzDwl4UDOFhAAFgBagJTVnIIR0g3T0FWQk4KLgjBpgESBDM0NTkYkmggshIoupmFAzCgmoUDOFhAAVgBagJTVnIIR0gyT1hVQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, Feb 7 - Sat, Feb 14 SJC San Jose ORD Chicago CA $365 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:07/02/2026TANYT&leg2=from:ORD,to:SJC,departure:14/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:364.80&airProductToken=AQpgCi4IwaYBEgQyNDkyGLISIJJoKN7GhAMws8eEAzhYQABYAWoCU1ZyCEdIMk9YVUJOCi4IwaYBEgQxNDkzGJJoIK4cKObIhAMw8cqEAzhYQAFYAWoCU1ZyCEdIMk9YVkJOCmAKLgjBpgESBDE0NzAYrhwgkmgovJKFAzDdlIUDOFhAAFgBagJTVnIIT0gyT1hVQk4KLgjBpgESBDIxMjcYkmggshIouJWFAzCYloUDOFhAAVgBagJTVnIIT0gyT1hVQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, Feb 7 - Sat, Feb 14 SJC San Jose ORD Chicago CA $393 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:07/02/2026TANYT&leg2=from:ORD,to:SJC,departure:14/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:392.70&airProductToken=AQpfCi4IwaYBEgQxMzExGLISIJIBKPTFhAMw_8aEAzhYQABYAWoCU1ZyCEdIMk9BVkJOCi0IwaYBEgM1MzgYkgEgrhwojsmEAzD-yoQDOFhAAVgBagJTVnIIT0gyT0FWQk4KYAouCMGmARIEMTQ3MBiuHCCSaCi8koUDMN2UhQM4WEAAWAFqAlNWcghPSDJPWFVCTgouCMGmARIEMjEyNxiSaCCyEii4lYUDMJiWhQM4WEABWAFqAlNWcghPSDJPWFVCThIKCAEQARgBKgJBUxgBIgQIARABKAIoAygEMAE) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, Dec 31 - Tue, Jan 6 SJC San Jose ORD Chicago CA $399 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:31/12/2025TANYT&leg2=from:ORD,to:SJC,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:398.10&airProductToken=AQpgCi4IwaYBEgQzNDU4GLISIJJoKMSYgQMwppmBAzhYQABYAWoCU1ZyCE9IMk9YVkJOCi4IwaYBEgQxNDc4GJJoIK4cKMqbgQMw2p2BAzhYQAFYAWoCU1ZyCE9IMk9YVUJOCmAKLgjBpgESBDE0NzAYrhwgkmgo79uBAzCP3oEDOFhAAFgBagJTVnIIR0gyT1hWQk4KLgjBpgESBDM0OTgYkmggshIo4eCBAzDG4YEDOFhAAVgBagJTVnIIT0gyT1hWQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, Feb 7 - Sat, Feb 14 SJC San Jose ORD Chicago CA $409 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:07/02/2026TANYT&leg2=from:ORD,to:SJC,departure:14/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:408.80&airProductToken=AQpgCi4IwaYBEgQyNDkyGLISIJJoKN7GhAMws8eEAzhYQABYAWoCU1ZyCEdIMk9YVUJOCi4IwaYBEgQxNDkzGJJoIK4cKObIhAMw8cqEAzhYQAFYAWoCU1ZyCEdIMk9YVUJOCmEKLgjBpgESAzMyNRiuHCDvuAEol5WFAzCyl4UDOFhAAFgBagJTVnIIT0gyT1hVQk4KLwjBpgESBDIyNzIY77gBILISKNqXhQMwzZiFAzhYQAFYAWoCU1ZyCE9IMk9YVUJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, Dec 31 - Tue, Jan 6 SJC San Jose ORD Chicago CA $413 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:31/12/2025TANYT&leg2=from:ORD,to:SJC,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:412.10&airProductToken=AQpgCi4IwaYBEgQzNDU4GLISIJJoKMSYgQMwppmBAzhYQABYAWoCU1ZyCE9IMk9YVkJOCi4IwaYBEgQxNDc4GJJoIK4cKMqbgQMw2p2BAzhYQAFYAWoCU1ZyCE9IMk9YVUJOCl4KLQjBpgESAzMzNxiuHCCSASio4IEDMMrigQM4WEAAWAFqAlNWcghPSDJPQVZCTgotCMGmARIDNzYxGJIBILISKPXigQMw_-OBAzhYQAFYAWoCU1ZyCEdIMk9BVkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, Feb 7 - Sat, Feb 14 SJC San Jose ORD Chicago CA $437 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:07/02/2026TANYT&leg2=from:ORD,to:SJC,departure:14/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:436.80&airProductToken=AQpfCi4IwaYBEgQxMzExGLISIJIBKPTFhAMw_8aEAzhYQABYAWoCU1ZyCEdIMk9BVkJOCi0IwaYBEgM1MzgYkgEgrhwojsmEAzD-yoQDOFhAAVgBagJTVnIIT0gyT0FWQk4KYQouCMGmARIDMzI1GK4cIO-4ASiXlYUDMLKXhQM4WEAAWAFqAlNWcghPSDJPWFVCTgovCMGmARIEMjI3MhjvuAEgshIo2peFAzDNmIUDOFhAAVgBagJTVnIIT0gyT1hVQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, Dec 31 - Tue, Jan 6 SJC San Jose ORD Chicago CA $462 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:31/12/2025TANYT&leg2=from:ORD,to:SJC,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:461.50&airProductToken=AQpgCi4IwaYBEgQzNDU4GLISIJJoKMSYgQMwppmBAzhYQABYAWoCU1ZyCE9IMk9YVkJOCi4IwaYBEgQxNDc4GJJoIK4cKMqbgQMw2p2BAzhYQAFYAWoCU1ZyCE9IMk9YVUJOCmEKLgjBpgESAzMyNRiuHCDvuAEovN6BAzDS4IEDOFhAAFgBagJTVnIIT0gyT1hVQk4KLwjBpgESBDIyNzIY77gBILISKNHigQMww-OBAzhYQAFYAWoCU1ZyCE9IMk9YVUJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, Dec 31 - Tue, Jan 6 SJC San Jose ORD Chicago CA $482 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:31/12/2025TANYT&leg2=from:ORD,to:SJC,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:481.90&airProductToken=AQpgCi4IwaYBEgQzNDU4GLISIJJoKMSYgQMwppmBAzhYQABYAWoCU1ZyCE9IMk9YVkJOCi4IwaYBEgQxNDc4GJJoIK4cKMqbgQMw2p2BAzhYQAFYAWoCU1ZyCE9IMk9YVUJOCl4KLQjBpgESAzcxNRiuHCCSASjQ2oEDMO3cgQM4WEAAWAFqAlNWcghPSDJPQVZCTgotCMGmARIDNjU3GJIBILISKJTegQMwoN-BAzhYQAFYAWoCU1ZyCFFIMk9BVkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Dec 24 - Fri, Dec 26 SJC San Jose MDW Chicago CA $1,084 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:MDW,departure:24/12/2025TANYT&leg2=from:MDW,to:SJC,departure:26/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1083.90&airProductToken=AQpuCjQIxJgBEgM4MDkYshIg4Fwor8yAAzDHzoADOFVAAFgBaglNQUlOQ0xBU0NyCFVBVk9BME1RCjYIxJgBEgQxMDc2GOBcIOywASiRz4ADMIbQgAM4VUABWAFqCU1BSU5DTEFTQ3IIVUFWT0EwTVEKbgo2CMSYARIEMjQxNxjssAEg4FwoheKAAzD84oADOFFAAFgBaglNQUlOQ0xBU0NyCFFBVk9BME1RCjQIxJgBEgM1NDkY4FwgshIoxeOAAzD85YADOFFAAVgBaglNQUlOQ0xBU0NyCFFBVk9BME1REgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=FTG_BF_PROMO_) ## Find the cheapest month to fly from San Jose (SJC) to Chicago (CHI) ### February is typically the cheapest month to fly From CA $153 - CA $498 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 $337 | | 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 $337 rising to CA $1,084.   Here are more money-saving tips:  - Fly in February 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.