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$99+ 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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Jan 21 — Jan 281
Tue 1/21
Tue 1/28
1 adult, Economy
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Cheap flight deals from Chicago to Oregon

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Oregon (USOR). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 16, 2025.

Round-trip from

$202
(Expedia)

One-way from

$99
(Alaska Airlines)
From Chicago (CHI) to Oregon
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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 January 16, 2025.

This Expedia deal was found by Cheapflights users on 1/16. 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.
Tue 2/254:05 pmORD - PDX
Nonstop4h 39mMultiple Airlines
Sun 3/28:28 pmPDX - ORD
1 stop7h 39mMultiple Airlines
Deal found 1/16$202
This Frontier deal was found by Cheapflights users on 1/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/119:09 pmMDW - PDX
1 stop13h 47mFrontier
Fri 4/189:01 amPDX - MDW
1 stop9h 13mFrontier
Deal found 1/14$203
This Mytrip deal was found by Cheapflights users on 1/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/110:47 pmORD - PDX
1 stop12h 34mSpirit Airlines
Wed 2/55:30 pmPDX - ORD
2 stops18h 53mSpirit Airlines
Deal found 1/15$203
This FlightHub deal was found by Cheapflights users on 1/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/610:47 pmORD - BOI
1 stop20h 56mSpirit Airlines
Mon 2/107:38 pmBOI - ORD
1 stop8h 53mSpirit Airlines
Deal found 1/16$210
This Southwest deal was found by Cheapflights users on 1/14. 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.
Tue 2/48:30 amMDW - PDX
Nonstop4h 25mSouthwest
Wed 2/199:00 amPDX - MDW
Nonstop3h 55mSouthwest
Deal found 1/14$212
This Alaska Airlines deal was found by Cheapflights users on 1/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/126:55 pmORD - PDX
Nonstop4h 46mAlaska Airlines
Wed 2/197:00 amPDX - ORD
Nonstop4h 04mAlaska Airlines
Deal found 1/15$212
This FlightHub deal was found by Cheapflights users on 1/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/136:50 amORD - PDX
1 stop19h 47mFrontier
Tue 2/186:32 amPDX - ORD
1 stop28h 53mFrontier
Deal found 1/16$215
This United Airlines deal was found by Cheapflights users on 1/16. 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.
Sat 2/159:11 amORD - PDX
Nonstop4h 43mUnited Airlines
Sat 2/227:05 amPDX - ORD
Nonstop4h 00mUnited Airlines
Deal found 1/16$227
This Delta deal was found by Cheapflights users on 1/15. 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.
Sat 3/157:13 pmMDW - BOI
1 stop5h 46mDelta
Sun 3/235:30 amBOI - MDW
1 stop7h 45mDelta
Deal found 1/15$229
This Delta deal was found by Cheapflights users on 1/16. 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.
Fri 4/46:45 pmORD - BOI
1 stop6h 27mDelta
Tue 4/155:40 amBOI - ORD
1 stop6h 51mDelta
Deal found 1/16$229
This Delta deal was found by Cheapflights users on 1/15. 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.
Tue 2/1110:19 amMDW - PDX
1 stop9h 13mDelta
Fri 2/2112:59 amPDX - MDW
1 stop7h 43mDelta
Deal found 1/15$232
This Delta deal was found by Cheapflights users on 1/15. 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.
Tue 2/112:25 pmORD - PDX
1 stop6h 29mDelta
Wed 2/195:15 amPDX - ORD
1 stop6h 00mDelta
Deal found 1/15$232

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 January 16, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 2/25

4:05 pm-6:44 pm

Nonstop4h 39m

Portland

Sun 3/2

8:28 pm-6:07 am

1 stop7h 39m

$202

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 4/11

9:09 pm-8:56 am

1 stop13h 47m

Portland

Fri 4/18

9:01 am-8:14 pm

1 stop9h 13m

$203

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 2/1

10:47 pm-9:21 am

1 stop12h 34m

Portland

Wed 2/5

5:30 pm-2:23 pm

2 stops18h 53m

$203

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Thu 2/6

10:47 pm-6:43 pm

1 stop20h 56m

Boise Air Term. Gowen Fld

Mon 2/10

7:38 pm-5:31 am

1 stop8h 53m

$210

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 2/4

8:30 am-10:55 am

Nonstop4h 25m

Portland

Wed 2/19

9:00 am-2:55 pm

Nonstop3h 55m

$212

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 2/12

6:55 pm-9:41 pm

Nonstop4h 46m

Portland

Wed 2/19

7:00 am-1:04 pm

Nonstop4h 04m

$212

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Sat 3/15

7:13 pm-11:59 pm

1 stop5h 46m

Boise Air Term. Gowen Fld

Sun 3/23

5:30 am-2:15 pm

1 stop7h 45m

$229

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 2/13

6:50 am-12:37 am

1 stop19h 47m

Portland

Thu 2/20

9:18 pm-5:00 am

1 stop29h 42m

$229

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Fri 4/4

6:45 pm-12:12 am

1 stop6h 27m

Boise Air Term. Gowen Fld

Wed 4/9

4:40 pm-11:59 pm

1 stop6h 19m

$229

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 2/11

10:19 am-5:32 pm

1 stop9h 13m

Portland

Fri 2/21

12:59 am-10:42 am

1 stop7h 43m

$232

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

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 January 16, 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 January 16, 2025.

The most flights from CHI to USOR are scheduled on a Thursday (13 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 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 January 16, 2025.
Get a feel of what it's like to fly with Frontier, 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.
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,681 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,511 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,964 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Alaska Airlines. According to our data, you can fly for as low as $99. Users have also found prices from $100 and $100 on Frontier and Spirit 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 Iberia (100%), Brussels Airlines (93%) and Qatar Airways (90%).

  • What are the cheapest flights from Chicago to Oregon?

    While on average a flight from Chicago to Oregon is generally $892, our data shows the cheapest flight currently is $98. When looking at the most popular route, (Chicago O'Hare Intl - Portland), you can expect to pay $137 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 January 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$83Average$138FlexibilityNo cancel feeOn-time65%
FrontierCheapest$118Average$211FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$173Average$434FlexibilityNo cancel feeOn-time75%
DeltaCheapest$176Average$440FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$194Average$332FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$218Average$517FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$228Average$425FlexibilityNo cancel feeOn-time63%
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