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$77+ 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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
ago. 4 — ago. 111
lun. 8/4
lun. 8/11
1 adult, Economy
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Cheap flight deals from Chicago to Oregon

Keep the following information in mind while searching for Chicago to Oregon flight deals. Data was last updated julio 30, 2025.

Round-trip from

$176
(Kiwi.com)

One-way from

$77
(Booking.com)

Popular in

December

Cheapest in

September

Average price

$317

Good round-trip deal

$166 or less

Good one-way deal

$144 or less
From Chicago (CHI) to Oregon
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One-way flight from Chicago (CHI) to Oregon
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Highest demand for flights based on searches. 4% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Oregon.
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Price to beat on a one-way flight from Chicago (CHI) to Oregon.
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Find 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 julio 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/237:00 amORD - PDX
Nonstop4h 25mHawaiian Airlines
sáb. 8/305:50 pmPDX - ORD
Nonstop4h 09mHawaiian Airlines
Deal found 7/30$176
This CheapOair deal was found by Cheapflights users on 7/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/16:00 amORD - PDX
1 stop7h 12mSpirit Airlines
mié. 10/298:04 pmPDX - ORD
1 stop6h 45mSpirit Airlines
Deal found 7/29$177
This Southwest deal was found by Cheapflights users on 7/29. 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.
sáb. 8/302:10 pmMDW - PDX
Nonstop4h 15mSouthwest
dom. 8/316:55 amPDX - MDW
Nonstop4h 00mSouthwest
Deal found 7/29$179
This Alaska Airlines deal was found by Cheapflights users on 7/30. 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.
sáb. 8/307:00 amORD - PDX
Nonstop4h 25mAlaska Airlines
dom. 8/317:00 amPDX - ORD
Nonstop4h 09mAlaska Airlines
Deal found 7/30$179
This American Airlines deal was found by Cheapflights users on 7/29. 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.
mié. 10/17:25 amORD - PDX
Nonstop4h 22mAmerican Airlines
mar. 10/71:23 pmPDX - ORD
Nonstop4h 07mAmerican Airlines
Deal found 7/29$197
This Delta deal was found by Cheapflights users on 7/30. 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.
sáb. 8/237:17 pmMDW - PDX
1 stop6h 14mDelta
sáb. 8/3010:57 pmPDX - MDW
1 stop7h 38mDelta
Deal found 7/30$208
This CheapOair deal was found by Cheapflights users on 7/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/137:00 amORD - PDX
1 stop6h 30mMultiple Airlines
lun. 8/187:52 pmPDX - ORD
1 stop6h 58mMultiple Airlines
Deal found 7/28$212
This Southwest deal was found by Cheapflights users on 7/29. 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.
sáb. 8/301:30 pmORD - PDX
1 stop9h 05mSouthwest
mar. 9/29:05 pmPDX - ORD
1 stop12h 45mSouthwest
Deal found 7/29$213
This United Airlines deal was found by Cheapflights users on 7/30. 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.
vie. 9/54:05 pmORD - PDX
Nonstop4h 26mUnited Airlines
vie. 9/122:15 pmPDX - ORD
Nonstop4h 10mUnited Airlines
Deal found 7/30$217
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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.
sáb. 9/2712:05 pmORD - BOI
1 stop7h 11mAlaska Airlines
lun. 9/298:46 pmBOI - ORD
1 stop9h 17mAlaska Airlines
Deal found 7/28$224
This Delta deal was found by Cheapflights users on 7/28. 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.
mié. 9/179:20 amMDW - BOI
1 stop5h 55mDelta
dom. 9/215:25 amBOI - MDW
1 stop6h 38mDelta
Deal found 7/28$225
This United Airlines deal was found by Cheapflights users on 7/28. 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.
sáb. 9/208:45 amORD - BOI
Nonstop3h 46mUnited Airlines
sáb. 9/272:12 pmBOI - ORD
1 stop8h 03mUnited Airlines
Deal found 7/28$225

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 julio 30, 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

sáb. 8/23

7:00 am-9:25 am

Nonstop4h 25m

Portland

sáb. 8/30

5:50 pm-11:59 pm

Nonstop4h 09m

$176

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

mié. 10/1

6:00 am-11:12 am

1 stop7h 12m

Portland

mié. 10/29

8:04 pm-4:49 am

1 stop6h 45m

$177

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

sáb. 8/30

2:10 pm-4:25 pm

Nonstop4h 15m

Portland

dom. 8/31

6:55 am-12:55 pm

Nonstop4h 00m

$179

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

sáb. 8/30

7:00 am-9:25 am

Nonstop4h 25m

Portland

dom. 8/31

7:00 am-1:09 pm

Nonstop4h 09m

$179

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

mié. 10/1

7:25 am-9:47 am

Nonstop4h 22m

Portland

mar. 10/7

1:23 pm-7:30 pm

Nonstop4h 07m

$197

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

mié. 8/27

3:00 pm-10:30 pm

1 stop9h 30m

Portland

dom. 8/31

6:35 am-5:55 pm

1 stop9h 20m

$207

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

sáb. 8/23

7:17 pm-11:31 pm

1 stop6h 14m

Portland

sáb. 8/30

10:57 pm-8:35 am

1 stop7h 38m

$208

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

mié. 8/13

7:00 am-11:30 am

1 stop6h 30m

Portland

lun. 8/18

7:52 pm-4:50 am

1 stop6h 58m

$212

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

vie. 9/5

4:05 pm-6:31 pm

Nonstop4h 26m

Portland

vie. 9/12

2:15 pm-8:25 pm

Nonstop4h 10m

$217

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

sáb. 9/27

12:05 pm-6:16 pm

1 stop7h 11m

Boise Air Term. Gowen Fld

lun. 9/29

8:46 pm-7:03 am

1 stop9h 17m

$224

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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, November is the cheapest month in which you can book a flight from Chicago to Oregon (average of $277). Flying from Chicago to Oregon in March is currently the most expensive (average of $368). 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 julio 30, 2025.

When flying from Chicago to Oregon, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 julio 30, 2025.

The most flights from CHI to USOR are scheduled on a Monday (28 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (12 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 julio 30, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Delta 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
10,000 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,241 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,980 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Hawaiian Airlines
7.8
Good
2,611 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,896 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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.

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $77. Users have also found prices from $99 and $99 on Southwest and Alaska 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 Midway - Portland or Chicago O'Hare Intl - Boise Air Term. Gowen Fld 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 Brussels Airlines (90%), Air Canada (82%) and United Airlines (81%).

  • What are the cheapest flights from Chicago to Oregon?

    While on average a flight from Chicago to Oregon is generally $760, our data shows the cheapest flight currently is $96. When looking at the most popular route, (Chicago O'Hare Intl - Portland), you can expect to pay $174 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, November is the cheapest month in which you can book a flight from Chicago to Oregon (average of $277). Flying from Chicago to Oregon in March is currently the most expensive (average of $368). 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.

See more FAQs

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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 julio 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$81Average$179FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$179FlexibilityNo cancel feeOn-time62%
DeltaCheapest$123Average$407FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$134Average$382FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$181Average$452FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$226Average$557FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$227Average$377FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$238Average$475FlexibilityNo cancel feeOn-time63%

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