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$100+ 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
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Cheap flight deals from Chicago to Oregon

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Oregon (USOR). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 18, 2024.

Round-trip from

$192
(Kiwi.com)

One-way from

$100
(Delta)
From Chicago (CHI) to Oregon
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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 December 18, 2024.

This Frontier deal was found by Cheapflights users on 12/16. 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.
Wed 12/256:00 amORD - PDX
1 stop11h 44mFrontier
Wed 1/112:45 pmPDX - ORD
1 stop9h 01mFrontier
Deal found 12/16$264
This FlightHub deal was found by Cheapflights users on 12/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/198:34 pmORD - PDX
1 stop23h 45mMultiple Airlines
Tue 12/317:48 pmPDX - ORD
1 stop7h 42mMultiple Airlines
Deal found 12/16$272
This Cheapflightsfares deal was found by Cheapflights users on 12/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2510:00 amORD - PDX
1 stop9h 30mSun Country Air
Mon 12/3011:59 pmPDX - ORD
1 stop15h 39mSun Country Air
Deal found 12/17$348
This American Airlines deal was found by Cheapflights users on 12/18. 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.
Mon 12/305:10 pmORD - BOI
1 stop6h 51mAmerican Airlines
Sun 1/52:05 pmBOI - ORD
1 stop9h 26mAmerican Airlines
Deal found 12/18$353
This FlightHub deal was found by Cheapflights users on 12/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2310:04 pmMDW - PDX
1 stop19h 40mFrontier
Sun 12/2910:46 amPDX - MDW
1 stop16h 47mFrontier
Deal found 12/16$383
This Mytrip deal was found by Cheapflights users on 12/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/319:35 pmORD - PDX
2 stops18h 14mSpirit Airlines
Tue 1/77:48 pmPDX - ORD
2 stops21h 00mSpirit Airlines
Deal found 12/17$391
This Delta deal was found by Cheapflights users on 12/17. 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.
Wed 12/254:00 pmORD - BOI
1 stop8h 10mDelta
Thu 12/262:35 pmBOI - ORD
1 stop7h 17mDelta
Deal found 12/17$393
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/297:35 amORD - PDX
1 stop9h 34mAmerican Airlines
Wed 1/86:00 amPDX - ORD
1 stop9h 45mAmerican Airlines
Deal found 12/17$396
This United deal was found by Cheapflights users on 12/18. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/317:35 pmORD - BOI
Nonstop4h 14mUnited Airlines
Tue 1/142:32 pmBOI - ORD
1 stop8h 27mUnited Airlines
Deal found 12/18$404
This Delta deal was found by Cheapflights users on 12/17. 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.
Wed 12/257:30 amORD - PDX
1 stop7h 09mDelta
Tue 12/315:20 amPDX - ORD
1 stop5h 55mDelta
Deal found 12/17$418
This Cheapflightsfares deal was found by Cheapflights users on 12/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/299:54 pmORD - BOI
1 stop14h 08mSpirit Airlines
Sun 1/127:38 pmBOI - ORD
1 stop8h 53mSpirit Airlines
Deal found 12/17$419
This Southwest deal was found by Cheapflights users on 12/16. 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.
Tue 12/311:45 pmORD - BOI
2 stops10h 15mSouthwest
Mon 1/63:30 pmBOI - ORD
1 stop6h 35mSouthwest
Deal found 12/16$428

Find flights from Chicago to Oregon within your budget

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 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 1/3

6:00 am-3:44 pm

1 stop11h 44m

Portland

Tue 1/7

7:48 pm-5:30 am

1 stop7h 42m

$192

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 1/22

8:15 am-12:07 am

1 stop17h 52m

Portland

Tue 3/18

10:06 am-12:17 am

1 stop12h 11m

$193

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 1/9

10:47 pm-9:21 am

1 stop12h 34m

Portland

Wed 1/15

5:30 pm-2:23 pm

2 stops18h 53m

$194

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 1/15

6:55 pm-9:41 pm

Nonstop4h 46m

Portland

Wed 1/22

7:00 am-1:07 pm

Nonstop4h 07m

$197

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 3/8

6:54 pm-7:40 am

1 stop14h 46m

Portland

Sun 3/16

9:18 pm-5:04 am

1 stop29h 46m

$205

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Mon 1/13

1:26 pm-8:35 pm

1 stop9h 09m

Portland

Tue 1/21

12:45 am-9:39 am

1 stop6h 54m

$208

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Mon 1/13

2:25 pm-6:54 pm

1 stop6h 29m

Portland

Thu 1/23

6:05 am-3:30 pm

1 stop7h 25m

$208

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Wed 1/22

1:39 pm-5:08 pm

1 stop29h 29m

Bend/Redmond

Sun 1/26

5:58 pm-7:28 pm

1 stop23h 30m

$211

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 1/16

8:10 pm-10:40 pm

Nonstop4h 30m

Portland

Thu 1/30

9:00 am-2:55 pm

Nonstop3h 55m

$218

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 5/6

8:20 pm-10:45 pm

Nonstop4h 25m

Portland

Tue 5/13

11:39 pm-5:45 am

Nonstop4h 06m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

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.

Travel insights for flights from Chicago to Oregon

Get recent, data-driven insights about flights from Chicago to Oregon including ideal travel times, pricing trends, and more.

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 $376). 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 18, 2024.

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.

Rainfall in Oregon by month

Plan your trip to Oregon by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Oregon ranges from 0.7 - 5.6 inches per month. November is typically the wettest month, when rainfall can reach 5.6 in. July is typically the driest time to visit Oregon when rainfall is around 0.7 in.

Temperature in Oregon by month

Plan your trip to Oregon by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Oregon, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 41.0 F).

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 18, 2024.
Get a feel of what it's like to fly with Spirit Airlines, Delta and Frontier from Chicago to Oregon by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,554 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,055 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Delta. According to our data, you can fly for as low as $100. Users have also found prices from $109 and $109 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 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 Qatar Airways (94%), American Airlines (92%) and Air Canada (90%).

  • What are the cheapest flights from Chicago to Oregon?

    While on average a flight from Chicago to Oregon is generally $626, our data shows the cheapest flight currently is $133. When looking at the most popular route, (Chicago O'Hare Intl - Portland), you can expect to pay $127 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 $376). 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 7 airlines flying from Chicago to Oregon

Discover the top 7 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 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$83Average$138FlexibilityNo cancel feeOn-time65%
FrontierCheapest$118Average$204FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$172Average$424FlexibilityNo cancel feeOn-time75%
DeltaCheapest$176Average$436FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$193Average$334FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$218Average$514FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$237Average$420FlexibilityNo cancel feeOn-time63%
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