Title: CA $176 Cheap Flights from Chicago (CHI) to Portland (PDX) - Expedia.ca

![View of Portland, Oregon overlooking the willamette river on a Fall Afternoon](https://images.trvl-media.com/place/178299/b61662af-dec4-42f2-b3cd-9aa834264b40.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/178299/b61662af-dec4-42f2-b3cd-9aa834264b40.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# CA $176 Cheap Flights from Chicago (CHI) to Portland (PDX)

[View CA $176 flight on Sat, May 2, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:ORD,to:PDX,departure:02/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:175.20&airProductToken=AQo0CjIIwYIBEgQxMjI5GK4cIO-4ASiy-osDMMH8iwM4QkAAWAFqBUJBU0lDcghRVkFaVVNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) 

## Popular airlines from Chicago to Portland, OR (PDX-Portland Intl.)

- ![](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:CHI,to:PDX,departure:17/04/2026TANYT&leg2=from:PDX,to:CHI,departure:24/04/2026TANYT&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_DL.svg)  
Delta  
[](https://www.expedia.ca/Flights-Search?leg1=from:CHI,to:PDX,departure:17/04/2026TANYT&leg2=from:PDX,to:CHI,departure:24/04/2026TANYT&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:CHI,to:PDX,departure:17/04/2026TANYT&leg2=from:PDX,to:CHI,departure:24/04/2026TANYT&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:CHI,to:PDX,departure:17/04/2026TANYT&leg2=from:PDX,to:CHI,departure:24/04/2026TANYT&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_WN.svg)  
Southwest Airlines  
[](https://www.expedia.ca/Flights-Search?leg1=from:CHI,to:PDX,departure:17/04/2026TANYT&leg2=from:PDX,to:CHI,departure:24/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}])
- ![](https://a.travel-assets.com/air/airlines/sy_sq.svg)  
Sun Country Airlines  
[](https://www.expedia.ca/Flights-Search?leg1=from:CHI,to:PDX,departure:17/04/2026TANYT&leg2=from:PDX,to:CHI,departure:24/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"SY"}}])
- ![](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:CHI,to:PDX,departure:17/04/2026TANYT&leg2=from:PDX,to:CHI,departure:24/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}])

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## Cheap flights from Chicago (CHI) to Portland (PDX)

Prices were available within the past 7 days and start at CA $176 for one-way flights and CA $349 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

All deals

One way

Roundtrip

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

Sat, Apr 25 - Sat, May 2

ORD

Chicago

PDX

Portland

CA $349

Roundtrip

found 2 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PDX,departure:25/04/2026TANYT&leg2=from:PDX,to:ORD,departure:02/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:348.30&airProductToken=AQo0CjIIwYIBEgQzMDk5GK4cIO-4ASiQq4sDMKWtiwM4QkAAWAFqBUJBU0lDcghRVkFaVVNCWAo0CjIIwYIBEgQyNTExGO-4ASCuHCi4-IsDMLr6iwM4QkAAWAFqBUJBU0lDcghRVkFaVVNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs)

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

Wed, Apr 29 - Tue, May 12

ORD

Chicago

PDX

Portland

CA $360

Roundtrip

found 6 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PDX,departure:29/04/2026TANYT&leg2=from:PDX,to:ORD,departure:12/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:359.50&airProductToken=AQoiCiAIwaYBEgMzMjUYrhwg77gBKKHViwMwtteLAzhYQABYAQojCiEIwaYBEgQxNDY0GO-4ASCuHCjE7IwDML3ujAM4WEAAWAESCggBEAEYASoCQVMYASIECAEQASgEMAE)

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

Sat, Apr 25 - Sat, May 2

ORD

Chicago

PDX

Portland

CA $365

Roundtrip

found 2 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PDX,departure:25/04/2026TANYT&leg2=from:PDX,to:ORD,departure:02/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:364.94&airProductToken=AQo0CjIIwYIBEgQzMDk5GK4cIO-4ASiQq4sDMKWtiwM4QkAAWAFqBUJBU0lDcghRVkFaVVNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs)

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

Tue, Apr 21 - Tue, May 5

ORD

Chicago

PDX

Portland

CA $373

Roundtrip

found 6 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PDX,departure:21/04/2026TANYT&leg2=from:PDX,to:ORD,departure:05/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:372.60&airProductToken=AQpFCiAIxJgBEgQyMjQyGK4cIPISKJ37igMw8PyKAzhFQABYAQohCMSYARIEMTIzOBjyEiDvuAEojv2KAzCE_ooDOEVAAVgBCkUKIQjEmAESBDQwMDgY77gBIJIBKM6VjAMwkZaMAzhFQABYAQogCMSYARIEMjA1NRiSASCuHCi3lowDMK-YjAM4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE)

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

Sat, Apr 25 - Sat, May 2

ORD

Chicago

PDX

Portland

CA $376

Roundtrip

found 2 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PDX,departure:25/04/2026TANYT&leg2=from:PDX,to:ORD,departure:02/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:375.70&airProductToken=AQpvCjUIxJgBEgQyMjMxGK4cIPISKJOliwMw7KaLAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTSDNCUQo2CMSYARIEMTIwORjyEiDvuAEosKeLAzClqIsDOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNIM0JRCnAKNgjEmAESAzU3MxjvuAEg47QBKJf8iwMwlP6LAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTSDNCUQo2CMSYARIENTIwNBjjtAEgrhwo0v6LAzCt_4sDOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNIM0JREgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ)

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

Sat, Apr 25 - Sat, May 2

ORD

Chicago

PDX

Portland

CA $379

Roundtrip

found 2 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PDX,departure:25/04/2026TANYT&leg2=from:PDX,to:ORD,departure:02/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:378.64&airProductToken=AQpvCjUIxJgBEgQzODQ5GK4cIMx8KM2kiwMwt6WLAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTSDNCUQo2CMSYARIEMjE2NxjMfCDvuAEo6qaLAzDFqIsDOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNIM0JREgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ)

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

Thu, Apr 30 - Tue, May 12

ORD

Chicago

PDX

Portland

CA $412

Roundtrip

found 6 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PDX,departure:30/04/2026TANYT&leg2=from:PDX,to:ORD,departure:12/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:411.70&airProductToken=AQpECiAIwaYBEgQxNDQ3GK4cIJJoKKThiwMwu-OLAzhYQABYAQogCMGmARIDNzkzGJJoIO-4ASi45IsDMODliwM4WEABWAEKIwohCMGmARIEMTQ2NBjvuAEgrhwoxOyMAzC97owDOFhAAFgBEgoIARABGAEqAkFTGAEiBAgBEAEoBDAB)

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

Sat, Apr 25 - Sat, May 2

ORD

Chicago

PDX

Portland

CA $418

Roundtrip

found 2 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PDX,departure:25/04/2026TANYT&leg2=from:PDX,to:ORD,departure:02/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:417.90&airProductToken=AQppCjIIwYIBEgQxNTIyGK4cIOKaASiOqIsDMJGpiwM4QkAAWAFqBUJBU0lDcghTVkFaVVNCWAozCMGCARIEMjUxNhjimgEg77gBKOqpiwMws6yLAzhCQAFYAWoFQkFTSUNyCFNWQVpVU0JYCjQKMgjBggESBDIxOTcY77gBIK4cKKL0iwMwnPaLAzhCQABYAWoFQkFTSUNyCFFWQVpVU0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw)

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

Tue, Apr 21 - Sun, May 3

ORD

Chicago

PDX

Portland

CA $426

Roundtrip

found 6 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PDX,departure:21/04/2026TANYT&leg2=from:PDX,to:ORD,departure:03/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:425.20&airProductToken=AQpFCiAIxJgBEgQyMjQyGK4cIPISKJ37igMw8PyKAzhFQABYAQohCMSYARIEMTIzOBjyEiDvuAEojv2KAzCE_ooDOEVAAVgBCkUKIQjEmAESBDQwMDgY77gBIJIBKI7_iwMw0f-LAzhFQABYAQogCMSYARIEMjA1NRiSASCuHCj3_4sDMO-BjAM4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE)

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

Wed, Apr 29 - Thu, May 21

ORD

Chicago

PDX

Portland

CA $536

Roundtrip

found 6 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PDX,departure:29/04/2026TANYT&leg2=from:PDX,to:ORD,departure:21/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:535.80&airProductToken=AQojCiEI1YIBEgQxNTU0GK4cIO-4ASjE1IsDMNHWiwM4S0AAWAEKIwohCNWCARIEMjA5NBjvuAEgrhwo1NGNAzDJ040DOExAAFgBEgoIARABGAEqAlVBGAEiBAgBEAEoBDAB)

## Alternative airports near Portland

Prices were available within the past 7 days. Prices and availability are subject to change.

[](https://www.expedia.ca/Flights-Search?leg1=from:ORD,to:PDX,departure:17/04/2026TANYT&leg2=from:PDX,to:ORD,departure:19/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE)

PDX

Portland Intl.

CheapestClosest

17 min

[Flights from CA $620

](https://www.expedia.ca/Flights-Search?leg1=from:ORD,to:PDX,departure:17/04/2026TANYT&leg2=from:PDX,to:ORD,departure:19/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) 

## Travel information

| Origin airport      | O'Hare Intl.                                                         |
| ------------------- | -------------------------------------------------------------------- |
| Destination airport | Portland Intl.                                                       |
| Airlines serving    | Alaska Airlines, American Airlines, Delta, Hawaiian Airlines, United |
| Roundtrip price     | CA $348                                                              |
| Distance            | 2774 km                                                              |

## Book with confidence

# Illinois to Portland Flights

**The easy way to book your flights from Chicago to Portland** 

With Expedia, it’s simple to find and book flights to Portland from Chicago 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 Portland Intl., 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 Chicago to Portland today, tomorrow, or this week. 

**Save dollars with cheap flights from CHI-All Airports, CHI to Portland Intl., PDX** 

Sort your search results by price to find great deals on your flight from Chicago to Portland—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Portland from Chicago currently is just CA $349 rising to CA $536\. 

Here are more money-saving tips: 

- Fly in April when flight prices are normally at their lowest
- Book about a month to 6 weeks before you travel for the best prices to Portland
- 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 Portland from Chicago** 

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\*Available to Expedia members.