HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Oregon

$92+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Oregon with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/27. 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 4/1610:55 am
ORD
-
PDX
1 stop26h 08m
Frontier
Sun 4/1911:48 am
PDX
-
ORD
1 stop20h 02m
Frontier
Deal found 1/27$202
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Fri 4/2410:55 am
ORD
-
PDX
1 stop26h 47m
Multiple Airlines
Thu 5/77:46 pm
PDX
-
ORD
1 stop19h 07m
Multiple Airlines
Deal found 1/27$203
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 4/2310:55 am
ORD
-
PDX
1 stop26h 08m
Frontier
Sun 5/311:48 am
PDX
-
ORD
1 stop20h 02m
Frontier
Deal found 1/27$204
This Southwest deal was found by Cheapflights users on 1/27. 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 2/248:25 am
MDW
-
PDX
1 stop7h 10m
Southwest
Tue 3/36:30 am
PDX
-
MDW
Nonstop3h 55m
Southwest
Deal found 1/27$207
This United Airlines deal was found by Cheapflights users on 1/26. 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 3/148:04 pm
ORD
-
PDX
Nonstop4h 41m
United Airlines
Mon 3/1611:59 pm
PDX
-
ORD
Nonstop3h 54m
United Airlines
Deal found 1/26$207
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Fri 4/1710:55 am
ORD
-
PDX
1 stop26h 47m
Frontier
Sat 4/2512:27 pm
PDX
-
ORD
2 stops16h 20m
Frontier
Deal found 1/28$209
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Fri 3/67:39 pm
ORD
-
PDX
1 stop17h 17m
Frontier
Mon 3/912:04 pm
PDX
-
ORD
2 stops25h 11m
Frontier
Deal found 1/28$210
This CheapOair deal was found by Cheapflights users on 1/27. 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.
Sat 5/99:18 pm
ORD
-
PDX
1 stop13h 41m
Frontier
Sat 5/1612:27 pm
PDX
-
ORD
1 stop19h 23m
Frontier
Deal found 1/27$212
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Sat 2/149:46 pm
ORD
-
PDX
Nonstop4h 31m
American Airlines
Tue 2/1711:35 pm
PDX
-
ORD
Nonstop3h 57m
American Airlines
Deal found 1/27$214
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/241:49 pm
MDW
-
PDX
1 stop8h 41m
Delta
Tue 3/312:09 pm
PDX
-
MDW
1 stop8h 24m
Delta
Deal found 1/28$217
This Alaska Airlines deal was found by Cheapflights users on 1/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/245:29 pm
ORD
-
PDX
1 stop8h 15m
Alaska Airlines
Tue 3/32:31 pm
PDX
-
ORD
1 stop7h 28m
Alaska Airlines
Deal found 1/28$217
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 4/57:55 am
ORD
-
PDX
2 stops29h 08m
Frontier
Wed 4/151:48 pm
PDX
-
ORD
1 stop18h 02m
Frontier
Deal found 1/27$218

Find flight deals from Chicago to Oregon

Keep the following information in mind while searching for Chicago to Oregon flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$202
(Kiwi.com)

One-way from

$92
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$308

Good round-trip deal

$244 or less

Good one-way deal

$134 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. 5% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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

MDW - PDX

MDWPDX

Chicago Midway

Wed 2/25

3:35 pm-6:00 pm

Nonstop4h 25m

Portland

Wed 3/4

9:55 am-9:05 pm

1 stop9h 10m

$207

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 2/17

2:07 pm-4:50 pm

Nonstop4h 43m

Portland

Fri 2/20

7:00 am-1:11 pm

Nonstop4h 11m

$207

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 5/9

7:55 pm-10:30 pm

Nonstop4h 35m

Portland

Sun 5/17

11:55 pm-6:00 am

Nonstop4h 05m

$207

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 2/17

8:10 am-10:45 am

Nonstop4h 35m

Portland

Wed 2/18

7:25 am-5:15 pm

1 stop7h 50m

$207

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 2/17

4:15 pm-6:49 pm

Nonstop4h 34m

Portland

Wed 2/18

11:59 pm-5:53 am

Nonstop3h 54m

$214

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 3/25

2:05 pm-8:25 pm

1 stop8h 20m

Portland

Mon 4/6

12:30 am-8:50 am

1 stop6h 20m

$217

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 2/18

7:40 am-12:42 pm

1 stop7h 02m

Portland

Sat 2/21

1:27 pm-11:52 pm

1 stop8h 25m

$217

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 3/25

6:00 am-10:33 am

1 stop6h 33m

Portland

Wed 4/1

7:03 am-1:13 pm

Nonstop4h 10m

$217

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 4/24

9:50 pm-12:10 am

Nonstop4h 20m

Portland

Mon 4/27

11:55 pm-5:50 am

Nonstop3h 55m

$217

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 4/17

2:05 pm-9:14 pm

1 stop9h 09m

Portland

Sat 4/25

11:59 pm-6:03 am

Nonstop4h 04m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 60 results
1
2
3
...
6

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, March is the cheapest month in which you can book a flight from Chicago to Oregon (average of $122). Flying from Chicago to Oregon in December is currently the most expensive (average of $207). 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 29, 2026.

One of the essential ways to save on airfare from Chicago to Oregon is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 25% 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 January 24, 2026.

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.

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 29, 2026.

The most flights from CHI to USOR are scheduled on a Monday (18 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

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 January 29, 2026.
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
11,807 reviews

Entertainment

7.0

Crew

8.5

Comfort

7.8

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,807 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Entertainment

7.0

Crew

8.5

Comfort

7.8

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Southwest
8.0
Very good
4,267 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Entertainment

7.0

Crew

8.5

Comfort

7.8

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Hawaiian Airlines
7.8
Good
2,830 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Entertainment

7.0

Crew

8.5

Comfort

7.8

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
United Airlines
7.4
Good
9,215 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Entertainment

7.0

Crew

8.5

Comfort

7.8

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
American Airlines
7.2
Good
11,206 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Entertainment

7.0

Crew

8.5

Comfort

7.8

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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 Southwest, Alaska Airlines, and United Airlines fly from Chicago to Oregon in about 4h 25m. The time it takes to get you to your destination is usually consistent. The distance from Chicago to Oregon is about 1746 mi. Most flights are nonstop.

  • 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 $90. Users have also found prices from $90 and $96 on Hawaiian Airlines and Frontier, 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 Malaysia Airlines (80%), British Airways (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 $670, our data shows the cheapest flight currently is $108. When looking at the most popular route, (Chicago O'Hare Intl - Portland), you can expect to pay $187 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, March is the cheapest month in which you can book a flight from Chicago to Oregon (average of $122). Flying from Chicago to Oregon in December is currently the most expensive (average of $207). 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Oregon

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Miami flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Orlando flights
O'Hare Intl to Denver flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Tampa flights
O'Hare Intl to LaGuardia flights
Midway to Dallas/Fort Worth flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to Newark flights
Midway to Fort Lauderdale flights
Midway to Sky Harbor Intl flights
Midway to Las Vegas flights
Midway to Miami flights
O'Hare Intl to Seattle flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to Atlanta flights
O'Hare Intl to West Palm Beach flights
O'Hare Intl to Sarasota flights
Midway to Orlando flights
O'Hare Intl to San Diego flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to Austin flights
O'Hare Intl to New Orleans flights
O'Hare Intl to Hobby flights
Midway to Los Angeles flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to Nashville flights
O'Hare Intl to Baltimore flights
O'Hare Intl to Ontario flights
O'Hare Intl to Dulles Intl flights
O'Hare Intl to Boston flights
O'Hare Intl to George Bush Intcntl flights
St. Louis to Las Vegas flights
O'Hare Intl to Honolulu flights
Midway to John F Kennedy Intl flights
Midway to Tampa flights
St. Louis to Orlando flights
Midway to Hobby flights
O'Hare Intl to Philadelphia flights
O'Hare Intl to Love Field flights
O'Hare Intl to Key West flights
O'Hare Intl to Palm Springs flights
Midway to Newark flights
Midway to Fort Myers flights

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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$86Average$178FlexibilityNo cancel feeOn-time65%
Hawaiian AirlinesCheapest$128Average$372FlexibilityNo cancel feeOn-time85%
DeltaCheapest$139Average$426FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$150Average$227FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$197Average$410FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$206Average$508FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$212Average$317FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$247Average$418FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.