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$78+ 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 7/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
mai 26 — juin 21
lun. 5/26
lun. 6/2
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 mai 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$179
(United Airlines)

One-way from

$78
(Southwest)

Popular in

December

Cheapest in

September

Average price

$275

Good round-trip deal

$261 or less

Good one-way deal

$132 or less
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
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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. 6% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in May 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 mai 21, 2025.

This United Airlines deal was found by Cheapflights users on 5/21. 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.
ven. 7/47:45 pmORD - BOI
Nonstop4h 07mUnited Airlines
jeu. 7/1012:39 pmBOI - ORD
Nonstop3h 26mUnited Airlines
Deal found 5/21$179
This Delta deal was found by Cheapflights users on 5/21. 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.
sam. 9/209:30 amORD - BOI
2 stops8h 18mDelta
sam. 10/1111:30 amBOI - ORD
1 stop5h 27mDelta
Deal found 5/21$180
This Delta deal was found by Cheapflights users on 5/20. 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.
ven. 7/47:21 pmMDW - BOI
1 stop5h 30mDelta
ven. 7/1111:40 pmBOI - MDW
1 stop9h 05mDelta
Deal found 5/20$197
This Southwest deal was found by Cheapflights users on 5/21. 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.
jeu. 7/38:00 pmMDW - BOI
1 stop5h 30mSouthwest
jeu. 7/102:50 pmBOI - MDW
Nonstop3h 20mSouthwest
Deal found 5/21$205
This Cheapflightsfares deal was found by Cheapflights users on 5/21. 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.
ven. 6/2711:50 amORD - PDX
1 stop7h 54mSpirit Airlines
dim. 6/296:39 pmPDX - ORD
1 stop14h 11mSpirit Airlines
Deal found 5/21$206
This Orbitz deal was found by Cheapflights users on 5/20. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/107:00 amORD - PDX
Nonstop4h 23mMultiple Airlines
sam. 6/146:39 pmPDX - ORD
1 stop14h 11mMultiple Airlines
Deal found 5/20$209
This Alaska Airlines deal was found by Cheapflights users on 5/20. 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.
mer. 9/106:20 amORD - BOI
1 stop9h 40mAlaska Airlines
dim. 9/145:45 pmBOI - ORD
1 stop12h 18mAlaska Airlines
Deal found 5/20$210
This Southwest deal was found by Cheapflights users on 5/19. 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.
dim. 8/318:20 pmMDW - PDX
Nonstop4h 15mSouthwest
ven. 9/51:35 pmPDX - MDW
Nonstop4h 00mSouthwest
Deal found 5/19$214
This Southwest deal was found by Cheapflights users on 5/20. 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.
sam. 8/22:50 pmORD - BOI
1 stop9h 10mSouthwest
mar. 8/54:05 pmBOI - ORD
1 stop6h 00mSouthwest
Deal found 5/20$215
This Alaska Airlines deal was found by Cheapflights users on 5/21. 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.
ven. 7/47:00 amORD - PDX
Nonstop4h 25mAlaska Airlines
mer. 7/95:35 pmPDX - ORD
Nonstop4h 04mAlaska Airlines
Deal found 5/21$223
This Orbitz deal was found by Cheapflights users on 5/20. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 7/106:00 amORD - BOI
1 stop10h 04mMultiple Airlines
dim. 7/1312:36 pmBOI - ORD
1 stop10h 34mMultiple Airlines
Deal found 5/20$223
This Delta deal was found by Cheapflights users on 5/20. 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.
ven. 7/44:30 pmORD - PDX
1 stop8h 07mDelta
ven. 7/1112:40 amPDX - ORD
1 stop5h 45mDelta
Deal found 5/20$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 mai 21, 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

ven. 7/4

7:45 pm-10:52 pm

Nonstop4h 07m

Boise Air Term. Gowen Fld

jeu. 7/10

12:39 pm-5:05 pm

Nonstop3h 26m

$179

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

sam. 9/20

9:30 am-4:48 pm

2 stops8h 18m

Boise Air Term. Gowen Fld

sam. 10/11

11:30 am-5:57 pm

1 stop5h 27m

$180

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

ven. 7/4

7:21 pm-11:51 pm

1 stop5h 30m

Boise Air Term. Gowen Fld

ven. 7/11

11:40 pm-9:45 am

1 stop9h 05m

$197

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

jeu. 7/3

8:00 pm-12:30 am

1 stop5h 30m

Boise Air Term. Gowen Fld

jeu. 7/10

2:50 pm-7:10 pm

Nonstop3h 20m

$205

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

ven. 6/27

11:50 am-5:44 pm

1 stop7h 54m

Portland

dim. 6/29

6:39 pm-10:50 am

1 stop14h 11m

$206

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

mar. 6/10

7:00 am-9:23 am

Nonstop4h 23m

Portland

sam. 6/14

6:39 pm-10:50 am

1 stop14h 11m

$209

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

mer. 9/10

6:20 am-3:00 pm

1 stop9h 40m

Boise Air Term. Gowen Fld

dim. 9/14

5:45 pm-7:03 am

1 stop12h 18m

$210

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

dim. 8/31

8:20 pm-10:35 pm

Nonstop4h 15m

Portland

ven. 9/5

1:35 pm-7:35 pm

Nonstop4h 00m

$214

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

sam. 8/2

2:50 pm-11:00 pm

1 stop9h 10m

Boise Air Term. Gowen Fld

mar. 8/5

4:05 pm-11:05 pm

1 stop6h 00m

$215

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

ven. 7/4

7:00 am-9:25 am

Nonstop4h 25m

Portland

mer. 7/9

5:35 pm-11:39 pm

Nonstop4h 04m

$223

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/21

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 mai 21, 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 mai 21, 2025.

The most flights from CHI to USOR are scheduled on a Monday (27 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 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 mai 21, 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

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Food

7.1

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

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Food

7.1

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
4,290 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Food

7.1

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
7,951 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Food

7.1

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
2,449 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Food

7.1

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
8,745 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Food

7.1

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 Southwest. According to our data, you can fly for as low as $78. Users have also found prices from $78 and $87 on United Airlines 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 (97%), Alaska Airlines (93%) and United Airlines (92%).

  • What are the cheapest flights from Chicago to Oregon?

    While on average a flight from Chicago to Oregon is generally $1,040, 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 $152 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.

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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 mai 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$84Average$139FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$183FlexibilityNo cancel feeOn-time62%
Hawaiian AirlinesCheapest$134Average$351FlexibilityNo cancel feeOn-time85%
DeltaCheapest$176Average$411FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$178Average$456FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$219Average$549FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$227Average$355FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$238Average$435FlexibilityNo cancel feeOn-time63%

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