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$67+ Cheap flights from Illinois 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PDX
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
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Cheap flight deals from Illinois to Oregon

Cheapest flights from Illinois to Oregon
Explore the most affordable flight options available from Illinois to Oregon. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 16, 2025.

This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/259:15 amORD - BOI
Nonstop4h 24mUnited Airlines
Tue 1/612:19 pmBOI - ORD
Nonstop3h 40mUnited Airlines
Deal found 12/16$252
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:00 amORD - BOI
1 stop5h 43mMultiple Airlines
Tue 1/63:45 pmBOI - ORD
1 stop7h 14mMultiple Airlines
Deal found 12/16$256
This Delta deal was found by Cheapflights users on 12/15. 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 1/61:40 pmBOI - ORD
1 stop9h 13mDelta
Deal found 12/15$272
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/177:10 amORD - BOI
1 stop7h 25mUnited Airlines
Thu 1/812:19 pmBOI - ORD
Nonstop3h 40mUnited Airlines
Deal found 12/16$306
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/259:08 amORD - PDX
Nonstop4h 50mUnited Airlines
Wed 12/312:35 pmPDX - ORD
1 stop7h 39mUnited Airlines
Deal found 12/16$307
This Kiwi.com deal was found by Cheapflights users on 12/13. 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.
Fri 12/267:44 pmORD - PDX
1 stop24h 24mMultiple Airlines
Tue 1/611:00 pmPDX - ORD
Nonstop4h 02mMultiple Airlines
Deal found 12/13$310
This Kiwi.com deal was found by Cheapflights users on 12/13. 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.
Fri 12/267:44 pmORD - PDX
1 stop24h 24mMultiple Airlines
Thu 1/111:00 pmPDX - ORD
Nonstop4h 02mMultiple Airlines
Deal found 12/13$311
This Kiwi.com deal was found by Cheapflights users on 12/13. 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.
Fri 12/267:44 pmORD - PDX
1 stop24h 24mMultiple Airlines
Sun 1/411:00 pmPDX - ORD
Nonstop4h 02mMultiple Airlines
Deal found 12/13$321
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/177:20 amORD - BOI
2 stops12h 31mDelta
Thu 1/81:40 pmBOI - ORD
1 stop9h 13mDelta
Deal found 12/16$321
This Kiwi.com deal was found by Cheapflights users on 12/13. 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.
Fri 12/267:44 pmORD - PDX
1 stop24h 24mMultiple Airlines
Mon 1/511:00 pmPDX - ORD
Nonstop4h 02mMultiple Airlines
Deal found 12/13$322
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/187:00 amORD - BOI
1 stop6h 42mAlaska Airlines
Tue 1/610:47 amBOI - ORD
1 stop12h 12mAlaska Airlines
Deal found 12/16$323
This Kiwi.com deal was found by Cheapflights users on 12/13. 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.
Fri 12/267:44 pmORD - PDX
1 stop24h 24mMultiple Airlines
Fri 1/910:29 amPDX - ORD
2 stops29h 12mMultiple Airlines
Deal found 12/13$324

Find flight deals from Illinois to Oregon

Keep the following information in mind while searching for Illinois to Oregon flight deals. Data was last updated December 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$192
(Kiwi.com)

One-way from

$67
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$417

Good round-trip deal

$280 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 Illinois to Oregon
Search Deals
One-way flight from Illinois to Oregon
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 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 Illinois to Oregon.
Search Deals
Price to beat on a one-way flight from Illinois to Oregon.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois 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 16, 2025.
Use the filters below to find and compare flights from Illinois to Oregon that are best for you.

Fly from

Illinois

Fly to

Oregon

Route

Depart

Return

Price

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 1/14

9:10 am-11:57 am

Nonstop4h 47m

Portland

Sun 1/18

8:30 am-6:46 pm

1 stop8h 16m

$227

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 1/20

2:06 pm-4:48 pm

Nonstop4h 42m

Portland

Wed 1/28

1:38 pm-11:50 pm

1 stop8h 12m

$227

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 3/13

2:07 pm-4:50 pm

Nonstop4h 43m

Portland

Tue 3/17

7:00 am-1:11 pm

Nonstop4h 11m

$227

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 1/6

4:15 pm-6:56 pm

Nonstop4h 41m

Portland

Thu 1/15

7:00 am-1:05 pm

Nonstop4h 05m

$227

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 2/17

2:07 pm-4:50 pm

Nonstop4h 43m

Portland

Sat 2/21

8:30 am-4:33 pm

1 stop6h 03m

$227

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Thu 1/22

6:06 pm-11:59 pm

1 stop6h 53m

Boise Air Term. Gowen Fld

Sun 1/25

6:23 am-2:38 pm

1 stop7h 15m

$228

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Mon 2/23

3:07 pm-11:30 pm

1 stop9h 23m

Boise Air Term. Gowen Fld

Fri 2/27

7:00 am-11:59 pm

1 stop15h 59m

$228

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Sat 2/7

8:00 am-3:10 pm

1 stop8h 10m

Boise Air Term. Gowen Fld

Wed 2/11

1:55 pm-11:50 pm

1 stop8h 55m

$228

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Thu 3/5

3:07 pm-11:30 pm

1 stop9h 23m

Boise Air Term. Gowen Fld

Mon 3/9

8:20 pm-1:11 pm

1 stop15h 51m

$228

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Thu 1/22

8:00 am-3:10 pm

1 stop8h 10m

Boise Air Term. Gowen Fld

Mon 1/26

3:43 pm-11:50 pm

1 stop7h 07m

$228

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

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

Have a flexible travel schedule? Discover the best time to fly to Oregon from Illinois 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 Illinois to Oregon

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

Currently, January is the cheapest month in which you can book a flight from Illinois to Oregon (average of $123). Flying from Illinois 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 IL to OR?

Find hourly flight availability from Illinois 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 16, 2025.

One of the essential ways to save on airfare from Illinois to Oregon is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 32% on airfare.

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

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

Travelers seeking maximum savings on their Illinois 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.

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 16, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest, and Hawaiian Airlines from Illinois to Oregon. 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
11,465 reviews

Entertainment

7.0

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

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
11,465 reviews
Alaska Airlines
8.0
Very good
11,465 reviews

Entertainment

7.0

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

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
4,250 reviews
Alaska Airlines
8.0
Very good
11,465 reviews

Entertainment

7.0

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

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
2,819 reviews
Alaska Airlines
8.0
Very good
11,465 reviews

Entertainment

7.0

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

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
9,094 reviews
Alaska Airlines
8.0
Very good
11,465 reviews

Entertainment

7.0

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

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
11,047 reviews
Alaska Airlines
8.0
Very good
11,465 reviews

Entertainment

7.0

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

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 Illinois 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 Illinois to Oregon?

    A quick flight from Illinois to Oregon can take about 4h 42m. United Airlines provides one of the quickest options available for as low as $227. Illinois and Oregon are separated by a distance of 1733 mi. This flight may include one or multiple stops.

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

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $55. However, be on the lookout for offers from Spirit Airlines and Hawaiian Airlines, as they are both options that can get you from Illinois to Oregon for a low price.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Illinois 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 Illinois to Oregon?

    Currently, January is the cheapest month in which you can book a flight from Illinois to Oregon (average of $123). Flying from Illinois 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.

See more FAQs

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Alternative routes for Illinois 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 Illinois to Oregon

Discover the top 8 airlines that operate flights from Illinois 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 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$86Average$182FlexibilityNo cancel feeOn-time65%
Hawaiian AirlinesCheapest$134Average$375FlexibilityNo cancel feeOn-time85%
FrontierCheapest$138Average$220FlexibilityNo cancel feeOn-time62%
DeltaCheapest$139Average$447FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$200Average$422FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$211Average$525FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$213Average$453FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$238Average$432FlexibilityNo cancel feeOn-time63%

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