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$53+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Nov 19 — Nov 261
1 adult
Tue 11/19
Tue 11/26
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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 November 14, 2024.

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 November 14, 2024.

This CheapOair deal was found by Cheapflights users on 11/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1212:43 pmMDW - PDX
1 stop23h 04mFrontier
Sun 12/158:33 pmPDX - MDW
1 stop13h 15mFrontier
Deal found 11/14$178
This CheapOair deal was found by Cheapflights users on 11/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/57:25 amORD - PDX
1 stop29h 38mFrontier
Sun 12/812:03 pmPDX - ORD
1 stop10h 36mFrontier
Deal found 11/14$179
This Expedia deal was found by Cheapflights users on 11/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/71:58 pmORD - PDX
Nonstop4h 31mMultiple Airlines
Sat 12/147:16 pmPDX - ORD
1 stop8h 14mMultiple Airlines
Deal found 11/13$181
This FareScan deal was found by Cheapflights users on 11/14. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/106:35 amORD - PDX
3 stops15h 53mSpirit Airlines
Sun 12/152:52 pmPDX - ORD
1 stop12h 38mSpirit Airlines
Deal found 11/14$183
This Alaska Airlines deal was found by Cheapflights users on 11/13. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/71:58 pmORD - PDX
Nonstop4h 31mAlaska Airlines
Sat 12/147:00 amPDX - ORD
Nonstop4h 02mAlaska Airlines
Deal found 11/13$197
This Delta deal was found by Cheapflights users on 11/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/71:45 pmORD - PDX
1 stop10h 18mDelta
Tue 12/1710:25 amPDX - ORD
1 stop5h 37mDelta
Deal found 11/14$216
This Mytrip deal was found by Cheapflights users on 11/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/46:33 pmORD - BOI
2 stops17h 25mSpirit Airlines
Sat 12/73:45 pmBOI - ORD
2 stops19h 20mSpirit Airlines
Deal found 11/14$255
This United Airlines deal was found by Cheapflights users on 11/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/98:11 pmORD - PDX
Nonstop4h 42mUnited Airlines
Mon 12/1611:59 pmPDX - ORD
Nonstop3h 49mUnited Airlines
Deal found 11/14$260
This Mytrip deal was found by Cheapflights users on 11/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/119:10 pmORD - BOI
1 stop14h 48mMultiple Airlines
Thu 12/125:28 pmBOI - ORD
2 stops17h 37mMultiple Airlines
Deal found 11/13$261
This Delta deal was found by Cheapflights users on 11/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/72:10 pmORD - EUG
1 stop6h 40mDelta
Tue 12/105:00 amEUG - ORD
1 stop6h 15mDelta
Deal found 11/13$265
This Alaska Airlines deal was found by Cheapflights users on 11/14. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/101:58 pmORD - BOI
2 stops11h 01mAlaska Airlines
Wed 12/112:47 pmBOI - ORD
1 stop8h 00mAlaska Airlines
Deal found 11/14$275
This United Airlines deal was found by Cheapflights users on 11/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/47:39 pmORD - BOI
Nonstop4h 05mUnited Airlines
Sat 12/75:26 pmBOI - ORD
1 stop5h 56mUnited Airlines
Deal found 11/14$279

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 2,752,363 searches. Data last updated November 14, 2024.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 12/13

12:43 pm-7:33 pm

1 stop8h 50m

Portland

Mon 12/16

12:03 pm-12:13 am

1 stop10h 10m

$178

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 2/18

8:00 am-11:40 pm

1 stop17h 40m

Portland

Sat 2/22

4:30 pm-4:47 am

1 stop10h 17m

$179

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 12/7

1:58 pm-4:29 pm

Nonstop4h 31m

Portland

Sat 12/14

7:16 pm-5:30 am

1 stop8h 14m

$181

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 12/10

6:35 am-8:28 pm

3 stops15h 53m

Portland

Sun 12/15

2:52 pm-5:30 am

1 stop12h 38m

$183

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 2/18

4:05 pm-6:44 pm

Nonstop4h 39m

Portland

Wed 2/19

7:00 am-1:04 pm

Nonstop4h 04m

$197

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 1/28

8:50 am-5:15 pm

1 stop10h 25m

Portland

Wed 2/5

9:00 am-2:55 pm

Nonstop3h 55m

$207

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 2/11

1:26 pm-5:35 pm

1 stop6h 09m

Portland

Fri 2/21

12:40 am-10:36 am

1 stop7h 56m

$216

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 2/18

6:59 pm-11:54 pm

1 stop6h 55m

Portland

Sat 2/22

6:04 am-4:38 pm

1 stop8h 34m

$216

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Thu 12/12

9:32 pm-3:03 pm

2 stops19h 31m

Bend/Redmond

Thu 12/19

4:50 pm-5:30 am

1 stop10h 40m

$229

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Tue 2/11

6:00 am-12:25 pm

1 stop7h 25m

Boise Air Term. Gowen Fld

Thu 2/20

5:30 am-1:20 pm

1 stop6h 50m

$248

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/14

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 $268). Flying from Chicago to Oregon in July is currently the most expensive (average of $341). 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 November 14, 2024.

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 November 14, 2024.

The most flights from CHI to USOR are scheduled on a Thursday (17 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 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 November 14, 2024.
Get a feel of what it's like to fly with Spirit Airlines, United Airlines and Alaska Airlines 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
5,045 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,045 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,439 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,788 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,194 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 Frontier. According to our data, you can fly for as low as $53. Users have also found prices from $81 and $89 on Spirit Airlines and American 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 Hawaiian Airlines (97%), Alaska Airlines (93%) and American Airlines (93%).

  • What are the cheapest flights from Chicago to Oregon?

    While on average a flight from Chicago to Oregon is generally $521, 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 $140 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 $268). Flying from Chicago to Oregon in July is currently the most expensive (average of $341). 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 2,752,363 searches. Data last updated November 14, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$83Average$139FlexibilityNo cancel feeOn-time65%
FrontierCheapest$118Average$210FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$165Average$417FlexibilityNo cancel feeOn-time75%
DeltaCheapest$176Average$434FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$194Average$381FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$217Average$515FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$237Average$458FlexibilityNo cancel feeOn-time63%
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