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$88+ Cheap flights from Chicago (CHI) to Oregon

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Chicago to Oregon

Cheapest flights from Chicago to Oregon
Explore the most affordable flight options available from Chicago to Oregon. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This Delta deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:00 amORD - BOI
1 stop9h 49mDelta
Tue 1/65:40 amBOI - ORD
1 stop6h 42mDelta
Deal found 12/10$272
This United Airlines deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/255:50 pmORD - PDX
1 stop7h 09mUnited Airlines
Thu 1/17:10 amPDX - ORD
Nonstop4h 05mUnited Airlines
Deal found 12/10$293
This Delta deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:00 amORD - BOI
1 stop9h 49mDelta
Mon 12/295:50 amBOI - ORD
1 stop5h 51mDelta
Deal found 12/10$302
This Frontier deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/221:32 pmORD - PDX
1 stop8h 18mFrontier
Tue 12/3012:47 pmPDX - ORD
1 stop9h 25mFrontier
Deal found 12/10$312
This American Airlines deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/215:25 pmORD - EUG
1 stop7h 45mAmerican Airlines
Wed 1/73:18 pmEUG - ORD
1 stop7h 05mAmerican Airlines
Deal found 12/10$314
This Frontier deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/221:32 pmORD - PDX
1 stop8h 18mFrontier
Thu 12/2512:47 pmPDX - ORD
1 stop9h 25mFrontier
Deal found 12/10$337
This Frontier deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/187:00 amORD - PDX
1 stop6h 43mFrontier
Sun 1/1112:10 pmPDX - ORD
1 stop6h 47mFrontier
Deal found 12/10$347
This Southwest deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/259:40 amMDW - PDX
1 stop11h 00mSouthwest
Thu 1/16:15 amPDX - MDW
Nonstop3h 55mSouthwest
Deal found 12/10$358
This Alaska Airlines deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/172:05 pmORD - EUG
1 stop10h 44mAlaska Airlines
Mon 12/291:00 pmEUG - ORD
1 stop14h 02mAlaska Airlines
Deal found 12/10$359
This Frontier deal was found by Cheapflights users on 12/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/217:00 amORD - PDX
1 stop6h 43mFrontier
Tue 12/3012:47 pmPDX - ORD
1 stop9h 25mFrontier
Deal found 12/9$362
This Frontier deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:00 amORD - PDX
1 stop6h 43mFrontier
Tue 12/3012:47 pmPDX - ORD
1 stop9h 25mFrontier
Deal found 12/11$363
This Delta deal was found by Cheapflights users on 12/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/97:02 pmMDW - BOI
1 stop6h 07mDelta
Wed 12/172:04 pmBOI - MDW
1 stop8h 43mDelta
Deal found 12/8$363

Find flight deals from Chicago to Oregon

Keep the following information in mind while searching for Chicago to Oregon flight deals. Data was last updated December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$184
(Kiwi.com)

One-way from

$88
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$403

Good round-trip deal

$273 or less

Good one-way deal

$118 or less
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
Search Deals
From Chicago (CHI) to Oregon
Search Deals
One-way flight from Chicago (CHI) to Oregon
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Oregon.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Oregon.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Oregon that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 12, 2025.
Use the filters below to find and compare flights from Chicago to Oregon that are best for you.

Fly from

Chicago

Fly to

Oregon

Route

Depart

Return

Price

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 1/10

9:10 am-12:00 pm

Nonstop4h 50m

Portland

Sat 1/17

1:24 pm-9:15 pm

1 stop5h 51m

$223

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 3/3

2:07 pm-4:50 pm

Nonstop4h 43m

Portland

Fri 3/13

7:00 am-1:11 pm

Nonstop4h 11m

$227

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 1/9

9:10 am-11:57 am

Nonstop4h 47m

Portland

Tue 1/13

7:00 am-1:05 pm

Nonstop4h 05m

$227

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 3/6

2:07 pm-4:50 pm

Nonstop4h 43m

Portland

Tue 3/10

7:00 am-1:11 pm

Nonstop4h 11m

$227

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Thu 1/22

3:35 pm-11:01 pm

1 stop8h 26m

Boise Air Term. Gowen Fld

Sun 1/25

6:23 am-2:38 pm

1 stop7h 15m

$228

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 2/14

2:07 pm-4:50 pm

Nonstop4h 43m

Portland

Wed 2/18

8:30 am-4:33 pm

1 stop6h 03m

$234

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 1/7

1:49 pm-8:12 pm

1 stop8h 23m

Portland

Wed 1/14

11:44 am-10:07 pm

1 stop8h 23m

$237

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 3/4

5:05 am-10:50 am

1 stop7h 45m

Portland

Sat 3/7

5:20 am-11:15 am

Nonstop3h 55m

$237

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 1/9

3:35 pm-6:00 pm

Nonstop4h 25m

Portland

Fri 1/16

6:45 am-12:40 pm

Nonstop3h 55m

$237

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 1/20

1:49 pm-8:32 pm

1 stop8h 43m

Portland

Sat 1/24

9:45 pm-9:53 am

1 stop10h 08m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Oregon

Have a flexible travel schedule? Discover the best time to fly to Oregon from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Oregon

What is the cheapest month to book a flight from Chicago to Oregon?

Currently, January is the cheapest month in which you can book a flight from Chicago to Oregon (average of $123). Flying from Chicago to Oregon in December is currently the most expensive (average of $207). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to OR?

Find hourly flight availability from Chicago to Oregon. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 12, 2025.

One of the essential ways to save on airfare from Chicago to Oregon is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 27% on airfare.

What is the cheapest day to fly from Chicago to Oregon?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Oregon. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Oregon flight should consider departing on Thursday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Oregon

Explore weekly flight availability from Chicago to Oregon. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 12, 2025.

The most flights from CHI to USOR are scheduled on a Wednesday (14 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 on average).

How much does it cost to fly round-trip from Chicago to Oregon?

Reviews of airlines servicing Oregon

Get insights into the airlines that provide service to Oregon. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Oregon. Reviews last updated December 12, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Hawaiian Airlines from Chicago to Oregon by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,431 reviews

Overall

8.0

Boarding

8.1

Comfort

7.8

Entertainment

7.0

Food

7.1

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Alaska Airlines
8.0
Very good
11,431 reviews
Alaska Airlines
8.0
Very good
11,431 reviews

Overall

8.0

Boarding

8.1

Comfort

7.8

Entertainment

7.0

Food

7.1

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Southwest
7.9
Good
4,252 reviews
Alaska Airlines
8.0
Very good
11,431 reviews

Overall

8.0

Boarding

8.1

Comfort

7.8

Entertainment

7.0

Food

7.1

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Hawaiian Airlines
7.8
Good
2,817 reviews
Alaska Airlines
8.0
Very good
11,431 reviews

Overall

8.0

Boarding

8.1

Comfort

7.8

Entertainment

7.0

Food

7.1

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
United Airlines
7.4
Good
9,095 reviews
Alaska Airlines
8.0
Very good
11,431 reviews

Overall

8.0

Boarding

8.1

Comfort

7.8

Entertainment

7.0

Food

7.1

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
American Airlines
7.2
Good
11,049 reviews
Alaska Airlines
8.0
Very good
11,431 reviews

Overall

8.0

Boarding

8.1

Comfort

7.8

Entertainment

7.0

Food

7.1

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Oregon. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Oregon?

    Airlines like United Airlines, Alaska Airlines, and Delta fly from Chicago to Oregon in about 4h 43m. The time it takes to get you to your destination can typically vary by up to 3h 40m. The distance from Chicago to Oregon is about 1733 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chicago to Oregon one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $55. Users have also found prices from $88 and $90 on Spirit Airlines and Hawaiian Airlines, respectively.

  • What are the most popular routes from Chicago to Oregon?

    When deciding which route to take from Chicago to Oregon consider Chicago O'Hare Intl - Portland, Chicago O'Hare Intl - Boise Air Term. Gowen Fld or Chicago Midway - Portland as they are the most popular.

  • What are the most reliable airlines from Chicago to Oregon?

    The top 3 most reliable airlines when flying from Chicago to Oregon are United Airlines (73%), Air Canada (71%) and SWISS (68%).

  • What are the cheapest flights from Chicago to Oregon?

    While on average a flight from Chicago to Oregon is generally $572, our data shows the cheapest flight currently is $108. When looking at the most popular route, (Chicago O'Hare Intl - Portland), you can expect to pay $205 for that flight.

  • Can I find deals for flights from Chicago to Oregon that include hotel bookings?

    Yes. In addition to deals on Chicago to Oregon flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Oregon?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Oregon.

  • Can I find deals for business class flights from Chicago to Oregon?

    Yes. Cheapflights offers flight deals from Chicago to Oregon by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Oregon?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Oregon (average of $123). Flying from Chicago to Oregon in December is currently the most expensive (average of $207). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for Chicago to Oregon

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Chicago to Oregon

Discover the top 8 airlines that operate flights from Chicago to Oregon. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$86Average$182FlexibilityNo cancel feeOn-time65%
Hawaiian AirlinesCheapest$134Average$375FlexibilityNo cancel feeOn-time85%
FrontierCheapest$138Average$217FlexibilityNo cancel feeOn-time62%
DeltaCheapest$203Average$447FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$207Average$424FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$216Average$322FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$217Average$538FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$238Average$432FlexibilityNo cancel feeOn-time63%

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