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$74+ 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$157
(Delta)

One-way from

$74
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$271

Good round-trip deal

$249 or less

Good one-way deal

$89 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. 8% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/125:25 amMDW - BOI
1 stop9h 40mSouthwest
Sat 11/155:00 amBOI - MDW
1 stop5h 45mSouthwest
Deal found 9/10$160
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Thu 10/25:35 amORD - BOI
1 stop7h 02mMultiple Airlines
Fri 10/39:26 pmBOI - ORD
1 stop13h 25mMultiple Airlines
Deal found 9/10$166
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/17:10 amORD - BOI
1 stop9h 30mDelta
Tue 10/75:25 amBOI - ORD
1 stop7h 05mDelta
Deal found 9/11$167
This Delta deal was found by Cheapflights users on 9/10. 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 11/128:50 amORD - BOI
1 stop6h 14mDelta
Sat 11/1511:13 amBOI - ORD
2 stops9h 23mDelta
Deal found 9/10$172
This Alaska Airlines deal was found by Cheapflights users on 9/11. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/143:25 pmORD - BOI
1 stop7h 55mAlaska Airlines
Sun 11/166:05 pmBOI - ORD
1 stop11h 17mAlaska Airlines
Deal found 9/11$178
This United Airlines deal was found by Cheapflights users on 9/9. 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.
Fri 10/34:05 pmORD - BOI
Nonstop3h 42mUnited Airlines
Sun 10/53:10 pmBOI - ORD
Nonstop3h 30mUnited Airlines
Deal found 9/9$179
This Southwest deal was found by Cheapflights users on 9/9. 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.
Sat 10/257:00 amORD - BOI
1 stop8h 05mSouthwest
Wed 10/294:15 pmBOI - ORD
1 stop5h 50mSouthwest
Deal found 9/9$180
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/246:08 amORD - BOI
2 stops10h 58mDelta
Mon 10/272:00 pmBOI - ORD
1 stop8h 50mDelta
Deal found 9/11$184
This United Airlines deal was found by Cheapflights users on 9/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/147:10 amORD - BOI
1 stop7h 34mUnited Airlines
Sun 11/1612:35 pmBOI - ORD
Nonstop3h 35mUnited Airlines
Deal found 9/11$185
This Southwest deal was found by Cheapflights users on 9/9. 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.
Thu 11/136:35 pmMDW - BOI
1 stop7h 00mSouthwest
Tue 11/183:45 pmBOI - MDW
1 stop6h 10mSouthwest
Deal found 9/9$187
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/227:15 amORD - BOI
1 stop29h 28mFrontier
Thu 10/3012:33 pmBOI - ORD
1 stop11h 10mFrontier
Deal found 9/9$188
This Delta deal was found by Cheapflights users on 9/9. 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 10/17:10 amORD - BOI
1 stop9h 30mDelta
Wed 10/82:00 pmBOI - ORD
1 stop8h 50mDelta
Deal found 9/9$193

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 September 11, 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

MDW - BOI

MDWBOI

Chicago Midway

Tue 3/3

9:20 am-10:05 pm

2 stops13h 45m

Boise Air Term. Gowen Fld

Wed 3/4

5:40 am-1:08 pm

1 stop6h 28m

$162

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Fri 10/3

4:05 pm-6:47 pm

Nonstop3h 42m

Boise Air Term. Gowen Fld

Sun 10/5

3:10 pm-7:40 pm

Nonstop3h 30m

$179

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Fri 10/24

2:25 pm-10:06 pm

1 stop8h 41m

Boise Air Term. Gowen Fld

Mon 10/27

2:00 pm-11:50 pm

1 stop8h 50m

$179

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Sat 10/25

7:00 am-2:05 pm

1 stop8h 05m

Boise Air Term. Gowen Fld

Wed 10/29

4:15 pm-11:05 pm

1 stop5h 50m

$180

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Thu 11/13

6:35 pm-12:35 am

1 stop7h 00m

Boise Air Term. Gowen Fld

Tue 11/18

3:45 pm-10:55 pm

1 stop6h 10m

$187

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Wed 10/1

5:30 pm-11:57 pm

1 stop7h 27m

Boise Air Term. Gowen Fld

Tue 10/7

9:00 am-9:43 pm

2 stops11h 43m

$198

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Thu 2/26

7:45 am-4:00 pm

1 stop9h 15m

Boise Air Term. Gowen Fld

Tue 3/3

1:30 pm-10:05 pm

2 stops7h 35m

$204

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 10/25

7:05 am-11:48 am

1 stop6h 43m

Portland

Sat 11/1

12:52 pm-2:59 pm

2 stops24h 07m

$207

ChicagoEugene

ORD - EUG

ORDEUG

Chicago O'Hare Intl

Sat 10/4

7:55 am-11:57 am

1 stop6h 02m

Eugene

Sat 10/11

7:00 am-5:18 pm

1 stop8h 18m

$209

ChicagoEugene

ORD - EUG

ORDEUG

Chicago O'Hare Intl

Wed 10/15

6:05 pm-11:14 pm

1 stop7h 09m

Eugene

Tue 10/28

7:00 am-5:10 pm

1 stop8h 10m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

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 September 11, 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 September 11, 2025.

The most flights from CHI to USOR are scheduled on a Tuesday (25 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 on average).

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 September 11, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Hawaiian Airlines 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

Overall

8.0

Entertainment

7.0

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.0

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,248 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.0

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Hawaiian Airlines
7.8
Good
2,723 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.0

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,937 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.0

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.0

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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.

  • How long is the flight from Chicago to Oregon?

    Airlines like Delta, United Airlines, and Southwest fly from Chicago to Oregon in about 3h 42m. The time it takes to get you to your destination can typically vary by up to 10h 03m. The distance from Chicago to Oregon is about 1432 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $77. Users have also found prices from $79 and $79 on Delta and United 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 United Airlines (81%), Brussels Airlines (75%) and Air Canada (74%).

  • What are the cheapest flights from Chicago to Oregon?

    While on average a flight from Chicago to Oregon is generally $729, 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 $154 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$86Average$185FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$179FlexibilityNo cancel feeOn-time62%
DeltaCheapest$123Average$427FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$134Average$375FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$184Average$433FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$218Average$385FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$227Average$570FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$238Average$451FlexibilityNo cancel feeOn-time63%

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