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$65+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 October 30, 2025.

This Frontier deal was found by Cheapflights users on 10/29. 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.
Sun 11/166:00 amORD - PDX
1 stop7h 56mFrontier
Sun 11/163:26 pmPDX - ORD
1 stop6h 49mFrontier
Deal found 10/29$208
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Sat 12/62:26 pmORD - PDX
2 stops23h 30mFrontier
Sat 12/139:48 amPDX - ORD
1 stop12h 25mFrontier
Deal found 10/30$209
This Priceline deal was found by Cheapflights users on 10/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/87:15 amORD - PDX
1 stop6h 41mFrontier
Fri 11/143:26 pmPDX - ORD
1 stop6h 49mFrontier
Deal found 10/29$213
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sun 12/146:50 amORD - PDX
1 stop11h 47mFrontier
Sun 12/2112:47 pmPDX - ORD
1 stop9h 25mFrontier
Deal found 10/29$215
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/139:22 pmORD - PDX
1 stop17h 01mMultiple Airlines
Mon 11/173:26 pmPDX - ORD
2 stops38h 02mMultiple Airlines
Deal found 10/29$216
This United Airlines deal was found by Cheapflights users on 10/30. 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.
Tue 12/27:44 pmORD - PDX
Nonstop4h 33mUnited Airlines
Sat 12/611:59 pmPDX - ORD
Nonstop3h 53mUnited Airlines
Deal found 10/30$217
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/411:44 amORD - PDX
2 stops26h 12mMultiple Airlines
Mon 12/85:32 pmPDX - ORD
1 stop10h 32mMultiple Airlines
Deal found 10/28$218
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Sun 12/79:52 pmORD - PDX
2 stops20h 45mFrontier
Sun 12/1412:51 pmPDX - ORD
1 stop9h 21mFrontier
Deal found 10/28$221
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/104:42 pmORD - PDX
2 stops21h 14mMultiple Airlines
Sat 12/139:48 amPDX - ORD
1 stop12h 25mMultiple Airlines
Deal found 10/29$222
This Booking.com deal was found by Cheapflights users on 10/29. 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.
Wed 11/56:05 pmORD - PDX
1 stop19h 51mFrontier
Sat 11/812:52 pmPDX - ORD
1 stop8h 37mFrontier
Deal found 10/29$224
This Mytrip deal was found by Cheapflights users on 10/30. 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.
Sun 12/147:00 amORD - PDX
1 stop6h 56mMultiple Airlines
Sun 12/216:50 pmPDX - ORD
1 stop13h 00mMultiple Airlines
Deal found 10/30$225
This Delta deal was found by Cheapflights users on 10/30. 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 12/61:50 pmMDW - PDX
1 stop9h 02mDelta
Fri 12/1212:32 amPDX - MDW
1 stop6h 47mDelta
Deal found 10/30$237

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$208
(Frontier)

One-way from

$65
(Frontier)

Popular in

December

Cheapest in

January

Average price

$314

Good round-trip deal

$263 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 Chicago (CHI) to Oregon
Search Deals
One-way flight from Chicago (CHI) to Oregon
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Oregon.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Oregon.
Search Deals

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 October 30, 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

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 12/17

8:55 am-4:43 pm

1 stop9h 48m

Portland

Tue 12/30

11:00 pm-5:02 am

Nonstop4h 02m

$227

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 12/12

2:05 pm-4:48 pm

Nonstop4h 43m

Portland

Tue 12/16

7:04 am-1:09 pm

Nonstop4h 05m

$247

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 1/8

8:00 am-1:48 pm

1 stop7h 48m

Portland

Mon 1/12

7:05 am-1:10 pm

Nonstop4h 05m

$247

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 12/9

2:05 pm-4:48 pm

Nonstop4h 43m

Portland

Sat 12/13

7:04 am-1:09 pm

Nonstop4h 05m

$247

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 12/10

2:05 pm-4:48 pm

Nonstop4h 43m

Portland

Sun 12/14

2:31 pm-11:50 pm

1 stop7h 19m

$253

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 12/11

1:50 pm-8:52 pm

1 stop9h 02m

Portland

Sun 12/14

11:20 pm-8:54 am

1 stop7h 34m

$257

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 12/12

2:14 pm-6:50 pm

1 stop6h 36m

Portland

Thu 12/18

1:45 pm-9:21 pm

1 stop5h 36m

$257

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Mon 12/1

9:05 am-11:48 am

Nonstop4h 43m

Portland

Wed 12/3

12:55 pm-10:56 pm

1 stop8h 01m

$260

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 11/26

12:47 pm-7:35 pm

1 stop8h 48m

Portland

Tue 12/2

12:32 am-9:19 am

1 stop6h 47m

$263

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Mon 12/8

3:05 pm-11:54 pm

1 stop10h 49m

Portland

Sun 12/14

7:04 am-1:09 pm

Nonstop4h 05m

$263

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

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, August is the cheapest month in which you can book a flight from Chicago to Oregon (average of $141). Flying from Chicago to Oregon in May is currently the most expensive (average of $199). 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 October 30, 2025.

One of the essential ways to save on airfare from Chicago to Oregon is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 24% on airfare.

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

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

Travelers seeking maximum savings on their Chicago 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.

How much does it cost to fly round-trip from Chicago to Oregon?

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 October 30, 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
11,214 reviews

Comfort

7.8

Entertainment

7.0

Crew

8.5

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
11,214 reviews
Alaska Airlines
8.0
Very good
11,214 reviews

Comfort

7.8

Entertainment

7.0

Crew

8.5

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Southwest
8.0
Very good
4,242 reviews
Alaska Airlines
8.0
Very good
11,214 reviews

Comfort

7.8

Entertainment

7.0

Crew

8.5

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Hawaiian Airlines
7.8
Good
2,797 reviews
Alaska Airlines
8.0
Very good
11,214 reviews

Comfort

7.8

Entertainment

7.0

Crew

8.5

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
8,998 reviews
Alaska Airlines
8.0
Very good
11,214 reviews

Comfort

7.8

Entertainment

7.0

Crew

8.5

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
American Airlines
7.2
Good
11,030 reviews
Alaska Airlines
8.0
Very good
11,214 reviews

Comfort

7.8

Entertainment

7.0

Crew

8.5

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

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 Alaska Airlines, Delta, and Southwest fly from Chicago to Oregon in about 7h 45m. The time it takes to get you to your destination can typically vary by up to 2h 03m. The distance from Chicago to Oregon is about 1746 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 Alaska Airlines. According to our data, you can fly for as low as $114. Users have also found prices from $118 and $119 on Southwest and Delta, 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 Alaska Airlines (84%), Hawaiian Airlines (84%) and Air Canada (81%).

  • What are the cheapest flights from Chicago to Oregon?

    While on average a flight from Chicago to Oregon is generally $1,348, our data shows the cheapest flight currently is $115. When looking at the most popular route, (Chicago O'Hare Intl - Portland), you can expect to pay $184 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, August is the cheapest month in which you can book a flight from Chicago to Oregon (average of $141). Flying from Chicago to Oregon in May is currently the most expensive (average of $199). 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$86Average$184FlexibilityNo cancel feeOn-time65%
DeltaCheapest$88Average$434FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$110Average$220FlexibilityNo cancel feeOn-time62%
Hawaiian AirlinesCheapest$134Average$375FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$198Average$424FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$213Average$302FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$226Average$537FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$238Average$432FlexibilityNo cancel feeOn-time63%

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