HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Oregon

$91+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Oregon with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 June 12, 2025.

Round-trip from

$190
(Cheapflightsfares)

One-way from

$91
(Delta)

Popular in

December

Cheapest in

September

Average price

$313

Good round-trip deal

$269 or less

Good one-way deal

$124 or less
From Chicago (CHI) to Oregon
Search Deals
One-way flight from Chicago (CHI) to Oregon
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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

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 June 12, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/283:21 pmORD - BOI
1 stop6h 23mSpirit Airlines
Fri 10/39:49 pmBOI - ORD
1 stop15h 27mSpirit Airlines
Deal found 6/11$190
This Delta deal was found by Cheapflights users on 6/10. 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.
Wed 8/209:15 amMDW - BOI
1 stop5h 46mDelta
Wed 10/221:43 pmBOI - MDW
1 stop7h 01mDelta
Deal found 6/10$195
This Delta deal was found by Cheapflights users on 6/10. 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.
Tue 7/87:20 pmORD - BOI
1 stop5h 49mDelta
Tue 7/1512:50 pmBOI - ORD
1 stop8h 18mDelta
Deal found 6/10$195
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/173:18 pmORD - MFR
1 stop25h 22mMultiple Airlines
Sun 7/209:51 pmMFR - ORD
1 stop14h 22mMultiple Airlines
Deal found 6/11$206
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/18:50 pmMDW - PDX
Nonstop4h 15mSouthwest
Fri 9/512:35 pmPDX - MDW
1 stop9h 15mSouthwest
Deal found 6/11$217
This Hawaiian Airlines deal was found by Cheapflights users on 6/11. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/182:07 pmORD - PDX
Nonstop4h 29mHawaiian Airlines
Mon 9/228:37 pmPDX - ORD
1 stop8h 26mHawaiian Airlines
Deal found 6/11$217
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/259:15 pmORD - PDX
1 stop16h 02mSpirit Airlines
Tue 7/16:39 pmPDX - ORD
1 stop14h 11mSpirit Airlines
Deal found 6/10$218
This Alaska Airlines deal was found by Cheapflights users on 6/10. 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.
Tue 10/76:00 amORD - RDM
1 stop14h 56mAlaska Airlines
Sat 10/113:40 pmRDM - ORD
1 stop6h 19mAlaska Airlines
Deal found 6/10$222
This Alaska Airlines deal was found by Cheapflights users on 6/10. 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 10/156:00 amORD - EUG
1 stop17h 29mAlaska Airlines
Mon 10/205:42 pmEUG - ORD
1 stop10h 39mAlaska Airlines
Deal found 6/10$224
This Hawaiian Airlines deal was found by Cheapflights users on 6/11. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/186:20 amORD - BOI
1 stop9h 40mHawaiian Airlines
Tue 9/236:35 amBOI - ORD
1 stop9h 14mHawaiian Airlines
Deal found 6/11$225
This Alaska Airlines deal was found by Cheapflights users on 6/10. 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.
Tue 7/292:03 pmORD - PDX
Nonstop4h 32mAlaska Airlines
Sat 8/25:35 pmPDX - ORD
Nonstop4h 04mAlaska Airlines
Deal found 6/10$227
This Trip.com deal was found by Cheapflights users on 6/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/267:00 amORD - EUG
1 stop6h 42mHawaiian Airlines
Sat 8/212:45 pmEUG - ORD
1 stop8h 54mHawaiian Airlines
Deal found 6/11$228

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 June 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

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Thu 9/4

3:21 pm-8:44 pm

1 stop6h 23m

Boise Air Term. Gowen Fld

Sun 9/7

9:49 pm-2:16 pm

1 stop15h 27m

$191

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Wed 8/20

9:15 am-2:01 pm

1 stop5h 46m

Boise Air Term. Gowen Fld

Wed 10/22

1:43 pm-9:44 pm

1 stop7h 01m

$195

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Tue 7/8

7:20 pm-12:09 am

1 stop5h 49m

Boise Air Term. Gowen Fld

Tue 7/15

12:50 pm-10:08 pm

1 stop8h 18m

$195

ChicagoMedford

ORD - MFR

ORDMFR

Chicago O'Hare Intl

Thu 7/17

3:18 pm-2:40 pm

1 stop25h 22m

Medford

Sun 7/20

9:51 pm-2:13 pm

1 stop14h 22m

$206

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Mon 9/1

8:50 pm-11:05 pm

Nonstop4h 15m

Portland

Fri 9/5

12:35 pm-11:50 pm

1 stop9h 15m

$217

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 7/26

7:00 am-9:25 am

Nonstop4h 25m

Portland

Tue 8/12

5:35 pm-11:39 pm

Nonstop4h 04m

$217

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 6/25

9:15 pm-11:17 am

1 stop16h 02m

Portland

Tue 7/1

6:39 pm-10:50 am

1 stop14h 11m

$218

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Tue 10/7

6:00 am-6:56 pm

1 stop14h 56m

Bend/Redmond

Sat 10/11

3:40 pm-11:59 pm

1 stop6h 19m

$222

ChicagoEugene

ORD - EUG

ORDEUG

Chicago O'Hare Intl

Wed 10/15

6:00 am-9:29 pm

1 stop17h 29m

Eugene

Mon 10/20

5:42 pm-6:21 am

1 stop10h 39m

$224

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 8/27

7:45 am-12:12 pm

1 stop6h 27m

Portland

Sat 8/30

12:46 am-8:24 am

1 stop5h 38m

$225

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 60 results
1
2
3
...
6

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 June 12, 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 June 12, 2025.

The most flights from CHI to USOR are scheduled on a Thursday (29 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 on average).

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 June 12, 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 stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,494 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 $91. Users have also found prices from $95 and $96 on Spirit Airlines and Southwest, 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 (95%), Alaska Airlines (93%) and United Airlines (91%).

  • What are the cheapest flights from Chicago to Oregon?

    While on average a flight from Chicago to Oregon is generally $571, our data shows the cheapest flight currently is $89. When looking at the most popular route, (Chicago O'Hare Intl - Portland), you can expect to pay $179 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Oregon

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Seattle flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Boston flights
O'Hare Intl to Newark flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Denver flights
O'Hare Intl to Orlando flights
O'Hare Intl to Miami flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Sky Harbor Intl flights
Midway to Newark flights
Midway to John F Kennedy Intl flights
O'Hare Intl to San Diego flights
O'Hare Intl to Philadelphia flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to Tampa flights
O'Hare Intl to Ontario flights
O'Hare Intl to Honolulu flights
O'Hare Intl to Portland flights
O'Hare Intl to Dulles Intl flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to Hobby flights
Midway to Las Vegas flights
Midway to LaGuardia flights
O'Hare Intl to George Bush Intcntl flights
Midway to Dallas/Fort Worth flights
O'Hare Intl to Atlanta flights
O'Hare Intl to Salt Lake City flights
St. Louis to Seattle flights
O'Hare Intl to Baltimore flights
O'Hare Intl to Burbank flights
St. Louis to LaGuardia flights
O'Hare Intl to Charlotte flights
Midway to Atlanta flights
O'Hare Intl to Nashville flights
O'Hare Intl to New Orleans flights
O'Hare Intl to Fort Myers flights
St. Louis to Las Vegas flights
St. Louis to Newark flights
O'Hare Intl to Austin flights
O'Hare Intl to Minneapolis flights
Midway to Dulles Intl flights
St. Louis to Denver flights
O'Hare Intl to Savannah flights
Midway to Orlando flights
Midway to Los Angeles flights

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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$91Average$143FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$183FlexibilityNo cancel feeOn-time62%
Hawaiian AirlinesCheapest$143Average$353FlexibilityNo cancel feeOn-time85%
DeltaCheapest$176Average$419FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$179Average$446FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$222Average$555FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$227Average$354FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$237Average$444FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.