Title: CA $157 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 $157 Cheap Flights from San Jose (SJC) to Chicago (CHI) [View CA $157 flight on Mon, Apr 27, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:SJC,to:ORD,departure:27/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:156.20&airProductToken=AQpgCi4IwaYBEgQzMDE1GLISIJJoKIC_iwMw2r-LAzhYQABYAWoCU1ZyCE9IMk9aSkJOCi4IwaYBEgQxNDkzGJJoIK4cKKTBiwMwm8OLAzhYQAFYAWoCU1ZyCE9IMk9aSkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ## Popular airlines from Norman Y. Mineta San Jose Intl. Airport (SJC) to Chicago - ![](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:20/03/2026TANYT&leg2=from:CHI,to:SJC,departure:27/03/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![](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:20/03/2026TANYT&leg2=from:CHI,to:SJC,departure:27/03/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![](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:20/03/2026TANYT&leg2=from:CHI,to:SJC,departure:27/03/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](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:20/03/2026TANYT&leg2=from:CHI,to:SJC,departure:27/03/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![](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:20/03/2026TANYT&leg2=from:CHI,to:SJC,departure:27/03/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![](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:20/03/2026TANYT&leg2=from:CHI,to:SJC,departure:27/03/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![](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:20/03/2026TANYT&leg2=from:CHI,to:SJC,departure:27/03/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"HA"}}]) - ![](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\* - ![](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\* - ![](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 $157 for one-way flights and CA $406 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) Wed, Mar 18 - Wed, Mar 25 SJC San Jose ORD Chicago CA $406 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:18/03/2026TANYT&leg2=from:ORD,to:SJC,departure:25/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:405.50&airProductToken=AQpgCi4IwaYBEgQzNDk5GLISIJJoKP_7hwMw2_yHAzhYQABYAWoCU1ZyCE9INE9BSkJOCi4IwaYBEgQxNDc4GJJoIK4cKPn8hwMwgv-HAzhYQAFYAWoCU1ZyCE9INE9BSkJOCmAKLgjBpgESBDE0NDcYrhwgkmgotsyIAzDTzogDOFhAAFgBagJTVnIIUUgyT1pKQk4KLgjBpgESBDM0NTkYkmggshIoss-IAzCW0IgDOFhAAVgBagJTVnIIUUgyT1pKQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, Mar 18 - Wed, Mar 25 SJC San Jose ORD Chicago CA $433 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:18/03/2026TANYT&leg2=from:ORD,to:SJC,departure:25/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:432.40&airProductToken=AQpgCi4IwaYBEgQzNDk5GLISIJJoKP_7hwMw2_yHAzhYQABYAWoCU1ZyCE9INE9BSkJOCi4IwaYBEgQxNDc4GJJoIK4cKPn8hwMwgv-HAzhYQAFYAWoCU1ZyCE9INE9BSkJOCl4KLQjBpgESAzM0ORiuHCCSASjUx4gDMOnJiAM4WEAAWAFqAlNWcghRSDJPWkpCTgotCMGmARIDNjU3GJIBILISKI7LiAMwk8yIAzhYQAFYAWoCU1ZyCFFIMk9aSkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, Aug 4 - Mon, Aug 17 SJC San Jose ORD Chicago CA $456 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:04/08/2026TANYT&leg2=from:ORD,to:SJC,departure:17/08/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:456.00&airProductToken=AQphCi8IwaYBEgQzMDMwGLISIO-4ASjBm5QDMLGclAM4WEAAWAFqAlNWcghPSDRPQUpCTgouCMGmARIDMzc2GO-4ASCuHCjGnZQDMLqflAM4WEABWAFqAlNWcghPSDRPQUpCTgpgCi4IwaYBEgQxNDcwGK4cIJJoKIqnlQMwnKmVAzhYQABYAWoCU1ZyCE5IN09BSkJOCi4IwaYBEgQyMDkxGJJoILISKNeplQMwsKqVAzhYQAFYAWoCU1ZyCE5IN09BSkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, Mar 18 - Wed, Mar 25 SJC San Jose ORD Chicago CA $483 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:18/03/2026TANYT&leg2=from:ORD,to:SJC,departure:25/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:482.41&airProductToken=AQpgCi4IwaYBEgQzNDk5GLISIJJoKP_7hwMw2_yHAzhYQABYAWoCU1ZyCE9INE9BSkJOCi4IwaYBEgQxNDc4GJJoIK4cKPn8hwMwgv-HAzhYQAFYAWoCU1ZyCE9INE9BSkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Mon, Mar 23 - Mon, Mar 30 SJC San Jose ORD Chicago CA $485 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:23/03/2026TANYT&leg2=from:ORD,to:SJC,departure:30/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:484.10&airProductToken=AQpoCjIIwYIBEgQ0OTY5GLISIO-5ASj4togDMPS3iAM4QkAAWAFqBUJBU0lDcghPVkFJWFNCWAoyCMGCARIEMTYxNBjvuQEgrhwosriIAzD_uYgDOEJAAVgBagVCQVNJQ3IIT1ZBSVhTQlgKmgEKMAjBggESAzkyMhiuHCChAyjxhokDMNCHiQM4QkAAWAFqBUJBU0lDcghPVkFJWFNCWAoyCMGCARIEMTI4NhihAyCjsQEo2IqJAzDpi4kDOEJAAVgBagVCQVNJQ3IIT1ZBS1ZTQlYKMgjBggESBDMxNDkYo7EBILISKJuMiQMwh46JAzhCQAFYAWoFQkFTSUNyCE9WQUtWU0JWEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, Aug 4 - Mon, Aug 17 SJC San Jose ORD Chicago CA $492 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:04/08/2026TANYT&leg2=from:ORD,to:SJC,departure:17/08/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:491.50&airProductToken=AQphCi8IwaYBEgQzMDMwGLISIO-4ASjBm5QDMLGclAM4WEAAWAFqAlNWcghPSDRPQUpCTgouCMGmARIDMzc2GO-4ASCuHCjGnZQDMLqflAM4WEABWAFqAlNWcghPSDRPQUpCTgphCi4IwaYBEgM0MTMYrhwg77gBKMSnlQMw0KmVAzhYQABYAWoCU1ZyCE5IMk9BSkJOCi8IwaYBEgQxNjMyGO-4ASCyEii3qpUDMKirlQM4WEABWAFqAlNWcghOSDJPQUpCThIKCAEQARgBKgJBUxgBIgQIARABKAIoAygEMAE) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, Aug 4 - Mon, Aug 17 SJC San Jose ORD Chicago CA $496 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:04/08/2026TANYT&leg2=from:ORD,to:SJC,departure:17/08/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:495.80&airProductToken=AQpgCi4IwaYBEgQzNDI5GLISIJJoKPeZlAMw1ZqUAzhYQABYAWoCU1ZyCFFINU9BSkJOCi4IwaYBEgQxNDkzGJJoIK4cKPealAMw95yUAzhYQAFYAWoCU1ZyCFFINU9BSkJOCmAKLgjBpgESBDE0NzAYrhwgkmgoiqeVAzCcqZUDOFhAAFgBagJTVnIITkg3T0FKQk4KLgjBpgESBDIwOTEYkmggshIo16mVAzCwqpUDOFhAAVgBagJTVnIITkg3T0FKQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sun, Apr 19 - Sun, Apr 26 SJC San Jose ORD Chicago CA $522 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:19/04/2026TANYT&leg2=from:ORD,to:SJC,departure:26/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:521.47&airProductToken=AQpgCi4IwaYBEgQyNDA5GLISIJJoKOvkigMwwOWKAzhYQABYAWoCU1ZyCFFINU9BSkJOCi4IwaYBEgQxNDkzGJJoIK4cKKbnigMwq-mKAzhYQAFYAWoCU1ZyCFFINU9BSkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, Aug 4 - Mon, Aug 17 SJC San Jose ORD Chicago CA $532 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:04/08/2026TANYT&leg2=from:ORD,to:SJC,departure:17/08/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:531.30&airProductToken=AQpgCi4IwaYBEgQxNjIzGLISIJJoKJOWlAMw75aUAzhYQABYAWoCU1ZyCFFINU9BSkJOCi4IwaYBEgQxNDc4GJJoIK4cKNyYlAMw4JqUAzhYQAFYAWoCU1ZyCFFINU9BSkJOCmEKLgjBpgESAzQxMxiuHCDvuAEoxKeVAzDQqZUDOFhAAFgBagJTVnIITkgyT0FKQk4KLwjBpgESBDE2MzIY77gBILISKLeqlQMwqKuVAzhYQAFYAWoCU1ZyCE5IMk9BSkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, Aug 4 - Mon, Aug 17 SJC San Jose ORD Chicago CA $536 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:04/08/2026TANYT&leg2=from:ORD,to:SJC,departure:17/08/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:535.60&airProductToken=AQpgCi4IwaYBEgQxNjIzGLISIJJoKJOWlAMw75aUAzhYQABYAWoCU1ZyCFFINU9BSkJOCi4IwaYBEgQxNDc4GJJoIK4cKNyYlAMw4JqUAzhYQAFYAWoCU1ZyCFFINU9BSkJOCmAKLgjBpgESBDE0NDcYrhwgkmgo6KqVAzCCrZUDOFhAAFgBagJTVnIIUUgyT0FTQk4KLgjBpgESBDE2MjQYkmggshIov6-VAzCcsJUDOFhAAVgBagJTVnIIUUgyT0FWQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=FTG_SPRING_PROMO_) ## Find the cheapest month to fly from San Jose (SJC) to Chicago (CHI) ### February is typically the cheapest month to fly From CA $155 - CA $498 per traveller. ## Travel information | Origin airport | Norman Y. Mineta San Jose Intl. | | ------------------- | ------------------------------- | | Destination airport | O'Hare Intl. | | Roundtrip price | CA $406 | | Distance | 2919 km | ## Book with confidence # 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 $406 rising to CA $536\. Here are more money-saving tips: - Fly in March 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. \*Available to Expedia members.