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$67+ 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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$198
(FlightHub)

One-way from

$67
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$333

Good round-trip deal

$288 or less

Good one-way deal

$118 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
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This FlightHub deal was found by Cheapflights users on 2/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/69:47 pmORD - BOI
1 stop15h 45mSpirit Airlines
Mon 3/101:31 pmBOI - ORD
1 stop16h 11mSpirit Airlines
Deal found 2/18$198
This Expedia deal was found by Cheapflights users on 2/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/77:00 amORD - BOI
1 stop7h 52mMultiple Airlines
Mon 4/142:34 pmBOI - ORD
1 stop14h 59mMultiple Airlines
Deal found 2/19$201
This FlightHub deal was found by Cheapflights users on 2/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2710:45 pmORD - PDX
1 stop12h 36mMultiple Airlines
Sat 3/19:00 amPDX - ORD
1 stop14h 01mMultiple Airlines
Deal found 2/19$222
This FlightHub deal was found by Cheapflights users on 2/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/289:56 pmORD - PDX
1 stop13h 25mSpirit Airlines
Sun 3/97:32 pmPDX - ORD
1 stop9h 10mSpirit Airlines
Deal found 2/19$223
This Trip.com deal was found by Cheapflights users on 2/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/18:44 pmMDW - PDX
1 stop13h 56mFrontier
Wed 3/56:32 amPDX - MDW
1 stop15h 45mFrontier
Deal found 2/20$228
This Delta deal was found by Cheapflights users on 2/20. 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.
Sat 4/267:00 pmMDW - BOI
1 stop5h 59mDelta
Tue 4/295:30 amBOI - MDW
1 stop7h 52mDelta
Deal found 2/20$229
This Delta deal was found by Cheapflights users on 2/20. 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.
Thu 4/178:50 amORD - BOI
1 stop6h 40mDelta
Sun 4/205:59 pmBOI - ORD
1 stop5h 54mDelta
Deal found 2/20$229
This American Airlines deal was found by Cheapflights users on 2/18. 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.
Wed 4/98:20 pmORD - PDX
Nonstop4h 42mAmerican Airlines
Mon 4/1411:52 pmPDX - ORD
Nonstop4h 05mAmerican Airlines
Deal found 2/18$232
This Booking.com deal was found by Cheapflights users on 2/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/297:59 pmORD - PDX
1 stop27h 46mFrontier
Sun 6/16:20 amPDX - ORD
1 stop15h 48mFrontier
Deal found 2/19$236
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/129:54 amMDW - PDX
1 stop10h 07mDelta
Tue 3/186:35 amPDX - MDW
1 stop5h 40mDelta
Deal found 2/19$237
This United Airlines deal was found by Cheapflights users on 2/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2912:45 pmORD - PDX
Nonstop4h 28mUnited Airlines
Tue 6/311:59 pmPDX - ORD
Nonstop4h 01mUnited Airlines
Deal found 2/19$238
This Delta deal was found by Cheapflights users on 2/20. 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.
Fri 4/42:20 pmORD - PDX
1 stop6h 25mDelta
Tue 4/812:59 amPDX - ORD
1 stop5h 43mDelta
Deal found 2/20$247

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 February 20, 2025.

Fly from

Chicago

Fly to

Oregon

Route

Depart

Return

Price

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Thu 3/6

9:47 pm-12:32 pm

1 stop15h 45m

Boise Air Term. Gowen Fld

Mon 3/10

1:31 pm-6:42 am

1 stop16h 11m

$198

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Mon 4/7

7:00 am-1:52 pm

1 stop7h 52m

Boise Air Term. Gowen Fld

Mon 4/14

2:34 pm-6:33 am

1 stop14h 59m

$201

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sun 4/6

6:45 am-12:44 am

1 stop19h 59m

Portland

Sun 4/13

9:27 pm-12:59 am

2 stops25h 32m

$222

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 3/7

9:16 am-1:38 pm

2 stops30h 22m

Portland

Mon 3/10

7:32 pm-8:21 am

2 stops34h 49m

$223

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 3/14

4:05 pm-6:44 pm

Nonstop4h 39m

Portland

Tue 3/18

10:06 am-12:23 am

1 stop12h 17m

$224

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 3/18

4:15 pm-6:48 pm

Nonstop4h 33m

Portland

Tue 3/25

7:31 pm-4:54 am

1 stop7h 23m

$228

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 4/5

8:59 pm-8:47 am

1 stop13h 48m

Portland

Sat 4/12

6:40 am-12:21 am

1 stop15h 41m

$228

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Sat 4/26

7:00 pm-11:59 pm

1 stop5h 59m

Boise Air Term. Gowen Fld

Tue 4/29

5:30 am-2:22 pm

1 stop7h 52m

$229

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Thu 4/17

8:50 am-2:30 pm

1 stop6h 40m

Boise Air Term. Gowen Fld

Sun 4/20

5:59 pm-12:53 am

1 stop5h 54m

$229

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 4/9

8:20 pm-11:02 pm

Nonstop4h 42m

Portland

Mon 4/14

11:52 pm-5:57 am

Nonstop4h 05m

$232

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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 February 20, 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 February 20, 2025.

The most flights from CHI to USOR are scheduled on a Monday (15 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 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 February 20, 2025.
Get a feel of what it's like to fly with Southwest, Alaska Airlines 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.
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Hawaiian Airlines
7.9
Good
2,317 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 Spirit Airlines. According to our data, you can fly for as low as $67. Users have also found prices from $94 and $109 on Frontier 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 (97%), Iberia (92%) and Lufthansa (85%).

  • What are the cheapest flights from Chicago to Oregon?

    While on average a flight from Chicago to Oregon is generally $770, our data shows the cheapest flight currently is $113. When looking at the most popular route, (Chicago O'Hare Intl - Portland), you can expect to pay $129 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$83Average$139FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$209FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$173Average$449FlexibilityNo cancel feeOn-time75%
DeltaCheapest$176Average$396FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$195Average$327FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$217Average$520FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$228Average$431FlexibilityNo cancel feeOn-time63%
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