Title: CA $163 Cheap Delta fights from San Diego to Chicago - 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 $163 Cheap Delta fights from San Diego (SAN) to Chicago (CHI)

[View CA $163 flight on Mon, Feb 23, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:SAN,to:MDW,departure:23/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:162.20&airProductToken=AQpwCjUIxJgBEgM3NjQYkmgg47QBKJL_hQMwmoGGAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTQTBCQwo3CMSYARIENTQwNRjjtAEg7LABKMaChgMwnoOGAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQTBCQxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) 

- [Roundtrip](?flightType=roundtrip)
- [One-way](?flightType=oneway)
- [Multi-city](?flightType=multicity)

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## Delta flights from San Diego to Chicago (SAN→CHI)

Prices were available within the past 7 days and start at CA $163 for one-way flights and CA $272 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)

Mon, Feb 23 - Wed, Feb 25

SAN

San Diego

ORD

Chicago

CA $272

Roundtrip

found 9 hours ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SAN,to:ORD,departure:23/02/2026TANYT&leg2=from:ORD,to:SAN,departure:25/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:271.19&airProductToken=AQptCjQIxJgBEgM4MTkYkmgg4FwonP-FAzCRgYYDOEVAAFgBaglNQUlOQkFTSUNyCFZBVlNBMEJDCjUIxJgBEgQxMTc4GOBcIK4cKJeChgMwmoOGAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQTBCQxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE)

![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif)

Mon, Feb 23 - Wed, Feb 25

SAN

San Diego

MDW

Chicago

CA $324

Roundtrip

found 9 hours ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SAN,to:MDW,departure:23/02/2026TANYT&leg2=from:MDW,to:SAN,departure:25/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:323.40&airProductToken=AQpuCjQIxJgBEgM4MTkYkmgg4FwonP-FAzCRgYYDOEVAAFgBaglNQUlOQkFTSUNyCFZBVlNBMEJDCjYIxJgBEgQxMDYzGOBcIOywASjlgoYDMNqDhgM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQkMKbwo2CMSYARIEMzY4MRjssAEgzHwo5ZCGAzDPkYYDOEVAAFgBaglNQUlOQkFTSUNyCFZBVlNBMEJDCjUIxJgBEgQyMTQ1GMx8IJJoKJKThgMwhZWGAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQTBCQxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE)

![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif)

Mon, Feb 23 - Wed, Feb 25

SAN

San Diego

ORD

Chicago

CA $324

Roundtrip

found 9 hours ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SAN,to:ORD,departure:23/02/2026TANYT&leg2=from:ORD,to:SAN,departure:25/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:323.40&airProductToken=AQpvCjUIxJgBEgM3NjQYkmgg47QBKJL_hQMwmoGGAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTQTBCQwo2CMSYARIEMTY1NBjjtAEgrhwo54KGAzDNg4YDOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNBMEJDCm8KNgjEmAESBDEzMDIYrhwg47QBKMmShgMwnpOGAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTQTBCQwo1CMSYARIDNzAwGOO0ASCSaCjTk4YDMIaWhgM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB)

![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif)

Mon, Feb 23 - Wed, Feb 25

SAN

San Diego

ORD

Chicago

CA $326

Roundtrip

found 9 hours ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SAN,to:ORD,departure:23/02/2026TANYT&leg2=from:ORD,to:SAN,departure:25/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:325.77&airProductToken=AQptCjQIxJgBEgM4MTkYkmgg4FwonP-FAzCRgYYDOEVAAFgBaglNQUlOQkFTSUNyCFZBVlNBMEJDCjUIxJgBEgQxMTc4GOBcIK4cKJeChgMwmoOGAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQTBCQxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE)

![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif)

Mon, Feb 23 - Wed, Feb 25

SAN

San Diego

ORD

Chicago

CA $334

Roundtrip

found 9 hours ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SAN,to:ORD,departure:23/02/2026TANYT&leg2=from:ORD,to:SAN,departure:25/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:333.06&airProductToken=AQptCjQIxJgBEgM4MTkYkmgg4FwonP-FAzCRgYYDOEVAAFgBaglNQUlOQkFTSUNyCFZBVlNBMEJDCjUIxJgBEgQxMTc4GOBcIK4cKJeChgMwmoOGAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQTBCQxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE)

![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif)

Mon, Feb 23 - Wed, Feb 25

SAN

San Diego

MDW

Chicago

CA $422

Roundtrip

found 9 hours ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SAN,to:MDW,departure:23/02/2026TANYT&leg2=from:MDW,to:SAN,departure:25/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:421.20&airProductToken=AQpwCjUIxJgBEgM3NjQYkmgg47QBKJL_hQMwmoGGAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTQTBCQwo3CMSYARIENTQwNRjjtAEg7LABKMaChgMwnoOGAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQTBCQwpuCjYIxJgBEgQyMDYxGOywASDgXCilkIYDMJaRhgM4RUAAWAFqCU1BSU5CQVNJQ3IIVEFWT0EwQlEKNAjEmAESAzczMRjgXCCSaCjnkYYDMIuUhgM4RUABWAFqCU1BSU5CQVNJQ3IIVEFWT0EwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB)

## Find the cheapest month to fly from San Diego (SAN) to Chicago (CHI)

### February is typically the cheapest month to fly

From CA $130 - CA $306 per traveller.

## Travel information

| Origin airport      | San Diego Intl. |
| ------------------- | --------------- |
| Destination airport | O'Hare Intl.    |
| Distance            | 2752 km         |

\*Available to Expedia members.