Title: CA $184 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 $184 Cheap Flights from San Jose (SJC) to Chicago (CHI) [View CA $184 flight on Thu, Jan 8, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:SJC,to:ORD,departure:08/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:183.40&airProductToken=AQpgCi4IwaYBEgQyNDkyGLISIJJoKJ71gQMw8_WBAzhYQABYAWoCU1ZyCEdIMk9RVkJOCi4IwaYBEgQxNDkzGJJoIK4cKKb3gQMwsfmBAzhYQAFYAWoCU1ZyCE9IMk9BVUJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) - [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:19/11/2025TANYT&leg2=from:chi,to:sjc,departure:26/11/2025TANYT&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:19/11/2025TANYT&leg2=from:chi,to:sjc,departure:26/11/2025TANYT&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:19/11/2025TANYT&leg2=from:chi,to:sjc,departure:26/11/2025TANYT&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:19/11/2025TANYT&leg2=from:chi,to:sjc,departure:26/11/2025TANYT&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:19/11/2025TANYT&leg2=from:chi,to:sjc,departure:26/11/2025TANYT&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:19/11/2025TANYT&leg2=from:chi,to:sjc,departure:26/11/2025TANYT&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:19/11/2025TANYT&leg2=from:chi,to:sjc,departure:26/11/2025TANYT&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 $184 for one-way flights and CA $436 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) Mon, Nov 24 - Wed, Dec 3 SJC San Jose ORD Chicago CA $436 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:24/11/2025TANYT&leg2=from:ORD,to:SJC,departure:03/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:435.50&airProductToken=AQpECiAIwaYBEgQzNDU4GLISIJJoKKT4_QIw_vj9AjhYQABYAQogCMGmARIEMTQ5MxiSaCCuHCib_f0CMIz__QI4WEABWAEKRAogCMGmARIEMTQ3MBiuHCCSaCi_3f4CMMrf_gI4WEAAWAEKIAjBpgESBDIwNTMYkmggshIop-D-AjCI4f4COFhAAVgBEgoIARABGAEqAkFTGAEiBAgBEAEoBDAB) ![Hawaiian Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/HA.gif) Mon, Nov 24 - Thu, Dec 4 SJC San Jose ORD Chicago CA $450 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:24/11/2025TANYT&leg2=from:ORD,to:SJC,departure:04/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:449.50&airProductToken=AQpECiAIyIIBEgQ3MDU4GLISIJJoKKT4_QIw_vj9AjhVQABYAQogCMiCARIENzQ5MxiSaCCuHCib_f0CMIz__QI4VUABWAEKRAogCMiCARIENzQ3MBiuHCCSaCjf6P4CMOrq_gI4VUAAWAEKIAjIggESBDY1NDgYkmggshIox-v-AjCo7P4COFVAAVgBEgoIARABGAEqAkhBGAEiBAgBEAEoBDAB) ![Hawaiian Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/HA.gif) Sat, Nov 22 - Tue, Dec 2 SJC San Jose ORD Chicago CA $478 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:22/11/2025TANYT&leg2=from:ORD,to:SJC,departure:02/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:477.40&airProductToken=AQpECiAIyIIBEgQ3MDU3GLISIJJoKOvn_QIwx-j9AjhVQABYAQogCMiCARIENjQxNhiSaCCuHCjP7f0CMMnv_QI4VUABWAEKRAogCMiCARIENzQ2NhiuHCCSaCjz1_4CMP_Z_gI4VUAAWAEKIAjIggESBDY1NDcYkmggshIojt_-AjDu3_4COFVAAVgBEgoIARABGAEqAkhBGAEiBAgBEAEoBDAB) ![Hawaiian Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/HA.gif) Sat, Nov 22 - Wed, Dec 3 SJC San Jose ORD Chicago CA $492 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:22/11/2025TANYT&leg2=from:ORD,to:SJC,departure:03/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:491.40&airProductToken=AQpECiAIyIIBEgQ3MDU3GLISIJJoKOvn_QIwx-j9AjhVQABYAQogCMiCARIENjQxNhiSaCCuHCjP7f0CMMnv_QI4VUABWAEKRAogCMiCARIENzQ3MBiuHCCSaCi_3f4CMMrf_gI4VUAAWAEKIAjIggESBDY1NDgYkmggshIop-D-AjCI4f4COFVAAVgBEgoIARABGAEqAkhBGAEiBAgBEAEoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Mon, Nov 24 - Tue, Dec 2 SJC San Jose ORD Chicago CA $541 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:24/11/2025TANYT&leg2=from:ORD,to:SJC,departure:02/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:540.84&airProductToken=AQpgCi4IwaYBEgQzNDI5GLISIJJoKIP8_QIw3Pz9AjhYQABYAWoCU1ZyCE5IMk9BVkJOCi4IwaYBEgQxNDkzGJJoIK4cKJv9_QIwjP_9AjhYQAFYAWoCU1ZyCE9IMk9BVUJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Nov 24 - Tue, Dec 2 SJC San Jose ORD Chicago CA $552 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:24/11/2025TANYT&leg2=from:ORD,to:SJC,departure:02/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:551.60&airProductToken=AQpuCjUIxJgBEgQzNjk2GLISIJIBKNf7_QIw6Pz9AjhFQABYAWoJTUFJTkJBU0lDcghUQVZOQTBCQwo1CMSYARIEMjEwOBiSASCuHCiz_f0CMKf__QI4RUABWAFqCU1BSU5CQVNJQ3IIVEFVU0EwQlEKbgo1CMSYARIEMTUzMxiuHCDMfCi-1f4CMJrW_gI4RUAAWAFqCU1BSU5CQVNJQ3IIWEFXTkEwQlEKNQjEmAESBDIwODcYzHwgshIo2db-AjDU2P4COEVAAVgBaglNQUlOQkFTSUNyCFhBV05BMEJREgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Nov 24 - Tue, Dec 2 SJC San Jose ORD Chicago CA $555 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:24/11/2025TANYT&leg2=from:ORD,to:SJC,departure:02/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:554.97&airProductToken=AQpuCjUIxJgBEgQzNjk2GLISIJIBKNf7_QIw6Pz9AjhFQABYAWoJTUFJTkJBU0lDcghUQVZOQTBCQwo1CMSYARIEMjEwOBiSASCuHCiz_f0CMKf__QI4RUABWAFqCU1BSU5CQVNJQ3IIVEFVU0EwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Hawaiian Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/HA.gif) Thu, Nov 27 - Wed, Dec 3 SJC San Jose ORD Chicago CA $569 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:27/11/2025TANYT&leg2=from:ORD,to:SJC,departure:03/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:568.80&airProductToken=AQpECiAIyIIBEgQ2OTUyGLISIJIBKNeZ_gIw55r-AjhVQABYAQogCMiCARIENjgxOBiSASCuHCjtm_4CMOqd_gI4VUABWAEKRAogCMiCARIENzQ3MBiuHCCSaCi_3f4CMMrf_gI4VUAAWAEKIAjIggESBDY1NDgYkmggshIop-D-AjCI4f4COFVAAVgBEgoIARABGAEqAkhBGAEiBAgBEAEoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Mon, Nov 24 - Tue, Dec 2 SJC San Jose ORD Chicago CA $657 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:24/11/2025TANYT&leg2=from:ORD,to:SJC,departure:02/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:657.00&airProductToken=AQpoCjIIwYIBEgQ0MjIwGLISIO-5ASje_P0CMNH9_QI4QkAAWAFqBUJBU0lDcghTVkFJWk5CWgoyCMGCARIEMTYxNBjvuQEgrhwo6v39AjC0__0COEJAAVgBagVCQVNJQ3IIU1ZBSVpOQloKaAoyCMGCARIEMjEwMxiuHCDvuQEotND-AjCa0v4COEJAAFgBagVCQVNJQ3IIT1dBSVpOQlgKMgjBggESBDM1NDQY77kBILISKLXS_gIwstP-AjhCQAFYAWoFQkFTSUNyCE9XQUlaTkJYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Wed, Nov 26 - Thu, Nov 27 SJC San Jose ORD Chicago CA $737 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:26/11/2025TANYT&leg2=from:ORD,to:SJC,departure:27/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:736.90&airProductToken=AQpDCiAI1YIBEgQxMzI1GLISIINpKIKT_gIwnZT-AjhUQABYAQofCNWCARIDMzc3GINpIK4cKNKU_gIw55X-AjhUQAFYAQohCh8I1YIBEgM0ODQYrhwgshIo5Zv-AjCFnv4COFRAAFgBEgoIARABGAEqAlVBGAEiBAgBEAEoBDAB) ## 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. ## Alternative airports near Chicago Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.ca/Flights-Search?leg1=from:SJC,to:ORD,departure:19/11/2025TANYT&leg2=from:ORD,to:SJC,departure:01/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ORD O'Hare Intl. Cheapest 23 min [Flights from CA $672](https://www.expedia.ca/Flights-Search?leg1=from:SJC,to:ORD,departure:19/11/2025TANYT&leg2=from:ORD,to:SJC,departure:01/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) [](https://www.expedia.ca/Flights-Search?leg1=from:SJC,to:MDW,departure:19/11/2025TANYT&leg2=from:MDW,to:SJC,departure:02/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) MDW Midway Intl. CheapestClosest 16 min [Flights from CA $672](https://www.expedia.ca/Flights-Search?leg1=from:SJC,to:MDW,departure:19/11/2025TANYT&leg2=from:MDW,to:SJC,departure:02/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) 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 $436 | | 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 $436 rising to CA $737.   Here are more money-saving tips:  - Fly in November 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.