What are the cheapest airlines to fly from Oregon to Chicago one-way?

To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $78. United Airlines flights start at $78 while deals on Alaska Airlines start at $87 one-way.

What are the most popular routes from Oregon to Chicago?

The most popular route from Oregon to Chicago is Portland - Chicago O'Hare Intl. You may also consider Portland - Chicago Midway or Boise Air Term. Gowen Fld - Chicago O'Hare Intl.

What are the cheapest flights from Oregon to Chicago?

Looking for the cheapest flight from Oregon to Chicago? While on average our users pay $949, our data indicates the cheapest price to be $120. The most popular route (Portland - Chicago O'Hare Intl), is priced around $156.

What are the most reliable airlines from Oregon to Chicago?

The top 3 most reliable airlines when flying from Oregon to Chicago are SWISS (95%), Brussels Airlines (90%) and Lufthansa (82%).

What are the most popular airlines that fly from Oregon to Chicago?

American Airlines, Alaska Airlines and Delta are the most popular airlines when flying from Oregon to Chicago.

How far in advance should I book a flight from Oregon to Chicago?

Travelers have found it’s best to book a flight 57 days in advance to save up to 19% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 57 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Oregon to Chicago 1-2 weeks in advance for as low as $297, or $354 for flights within the next 24 hours.

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

Our data shows that January tends to be the cheapest month to fly to Chicago from Oregon. Users have commonly found prices around $339 for the month, but tickets can be as low as $178. Due to multiple factors, prepare for potentially higher prices in March.

Can I find deals for flights from Oregon to Chicago that include hotel bookings?

Yes. In addition to deals on Oregon to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Oregon to Chicago?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oregon to Chicago.

Can I find deals for business class flights from Oregon to Chicago?

Yes. Cheapflights offers flight deals from Oregon to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$78+ Flights from Oregon to Chicago

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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”

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Cheap flight deals from Oregon to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$175 (Delta)
One-way from	$78 (Southwest)
Popular in	March
Cheapest in	January
Average price	$342
Good round-trip deal	$358 or less
Good one-way deal	$170 or less

Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.

Search Deals

Provider most trusted by Cheapflights users for Portland-Chicago (CHI) flights.

Search Deals

From Oregon to Chicago (CHI)

Search Deals

One-way flight from Oregon to Chicago (CHI)

Search Deals

Highest demand for flights based on searches. 10% potential increase in price ($38 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in April 2025

Search Deals

Price to beat on a round-trip flight from Oregon to Chicago (CHI).

Search Deals

Price to beat on a one-way flight from Oregon to Chicago (CHI).

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Find flight deals from Oregon to Chicago

Cheapest flights from Oregon to Chicago
Explore the most affordable flight options available from Oregon to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 22, 2025.

Wed 7/210:24 amBOI - MDW

1 stop6h 16mDelta

Mon 7/79:20 amMDW - BOI

1 stop5h 40mDelta

Deal found 4/21

$175

Sat 5/2412:50 pmBOI - ORD

1 stop7h 50mDelta

Thu 5/291:40 pmORD - BOI

1 stop5h 41mDelta

Deal found 4/22

$175

Fri 6/275:42 pmBOI - ORD

1 stop5h 48mUnited Airlines

Mon 6/308:45 amORD - BOI

Nonstop3h 58mUnited Airlines

Deal found 4/22

$201

Fri 7/41:30 pmBOI - MDW

1 stop6h 25mSouthwest

Fri 7/1110:30 amMDW - BOI

Nonstop3h 35mSouthwest

Deal found 4/21

$205

Wed 5/211:02 pmRDM - ORD

1 stop8h 54mAlaska Airlines

Wed 5/287:00 amORD - RDM

1 stop7h 22mAlaska Airlines

Deal found 4/21

$234

Sun 5/115:40 pmPDX - ORD

2 stops13h 15mMultiple Airlines

Fri 5/165:21 pmORD - PDX

1 stop9h 17mMultiple Airlines

Deal found 4/22

$236

Thu 6/55:51 pmPDX - ORD

Nonstop4h 05mHawaiian Airlines

Tue 6/107:00 amORD - PDX

Nonstop4h 23mHawaiian Airlines

Deal found 4/22

$238

Thu 5/156:20 amPDX - MDW

1 stop10h 48mFrontier

Sun 5/186:15 amMDW - PDX

1 stop11h 27mFrontier

Deal found 4/22

$238

Thu 5/225:40 pmPDX - ORD

1 stop15h 15mSpirit Airlines

Tue 5/279:14 pmORD - PDX

2 stops17h 28mSpirit Airlines

Deal found 4/22

$239

Wed 5/2112:30 pmRDM - ORD

1 stop7h 10mDelta

Wed 5/281:40 pmORD - RDM

2 stops11h 16mDelta

Deal found 4/21

$240

Tue 5/202:14 pmPDX - ORD

Nonstop4h 03mUnited Airlines

Tue 5/275:02 amORD - PDX

1 stop6h 37mUnited Airlines

Deal found 4/22

$242

Fri 5/301:25 pmPDX - ORD

1 stop6h 58mAlaska Airlines

Mon 6/27:00 amORD - PDX

Nonstop4h 23mAlaska Airlines

Deal found 4/22

$244

Best flights from Oregon to Chicago
Discover carefully curated flight deals from Oregon to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 22, 2025.

Wed 7/210:24 amBOI - MDW

1 stop6h 16mDelta

Mon 7/79:20 amMDW - BOI

1 stop5h 40mDelta

Deal found 4/21

$175

Fri 6/275:42 pmBOI - ORD

1 stop5h 48mUnited Airlines

Mon 6/308:45 amORD - BOI

Nonstop3h 58mUnited Airlines

Deal found 4/22

$201

Wed 10/16:05 pmBOI - MDW

1 stop9h 55mSouthwest

Mon 10/65:10 amMDW - BOI

1 stop5h 35mSouthwest

Deal found 4/22

$220

Wed 5/211:02 pmRDM - ORD

1 stop8h 54mAlaska Airlines

Wed 5/287:00 amORD - RDM

1 stop7h 22mAlaska Airlines

Deal found 4/21

$234

Thu 5/156:20 amPDX - MDW

1 stop10h 48mFrontier

Sun 5/186:15 amMDW - PDX

1 stop11h 27mFrontier

Deal found 4/22

$238

Sun 6/1512:12 pmPDX - ORD

2 stops19h 14mSpirit Airlines

Tue 6/1711:50 amORD - PDX

1 stop7h 54mSpirit Airlines

Deal found 4/21

$241

Wed 5/215:40 pmPDX - ORD

1 stop9h 45mMultiple Airlines

Mon 5/267:00 amORD - PDX

Nonstop4h 23mMultiple Airlines

Deal found 4/21

$245

Tue 5/66:30 amBOI - ORD

1 stop9h 30mHawaiian Airlines

Wed 5/73:44 pmORD - BOI

1 stop7h 55mHawaiian Airlines

Deal found 4/21

$246

Sat 5/246:00 amPDX - ORD

1 stop7h 55mAmerican Airlines

Fri 5/308:25 pmORD - PDX

Nonstop4h 34mAmerican Airlines

Deal found 4/21

$270

Sun 6/1511:59 pmPDX - ORD

1 stop15h 22mSun Country Air

Thu 6/196:17 pmORD - PDX

1 stop6h 29mSun Country Air

Deal found 4/22

$285

Wed 7/210:24 amBOI - ORD

1 stop5h 22mDelta

Mon 7/76:00 amORD - BOI

1 stop5h 57mDelta

Deal found 4/21

$175

Tue 5/202:14 pmPDX - ORD

Nonstop4h 03mUnited Airlines

Tue 5/275:02 amORD - PDX

1 stop6h 37mUnited Airlines

Deal found 4/22

$242

Last-minute flights from Oregon to Chicago
Discover last-minute flight deals from Oregon to Chicago. Data last updated April 22, 2025 and is based on user searches.

Mon 4/285:00 pmBOI - MDW

1 stop6h 05mSouthwest

Tue 4/298:40 amMDW - BOI

1 stop6h 45mSouthwest

Deal found 4/21

$340

Thu 5/17:01 pmPDX - ORD

1 stop9h 32mSpirit Airlines

Wed 5/711:50 amORD - PDX

1 stop6h 55mSpirit Airlines

Deal found 4/21

$242

Thu 5/17:01 pmPDX - ORD

1 stop9h 32mMultiple Airlines

Sat 5/311:53 amORD - PDX

2 stops25h 33mMultiple Airlines

Deal found 4/21

$286

Thu 5/18:59 pmBOI - ORD

1 stop8h 06mAlaska Airlines

Fri 5/29:00 amORD - BOI

1 stop8h 55mAlaska Airlines

Deal found 4/22

$353

Thu 5/111:30 pmBOI - MDW

1 stop8h 37mDelta

Fri 5/27:00 pmMDW - BOI

1 stop6h 03mDelta

Deal found 4/21

$359

Thu 5/14:40 pmBOI - ORD

1 stop6h 19mDelta

Fri 5/25:05 pmORD - BOI

2 stops7h 58mDelta

Deal found 4/22

$364

Thu 5/17:00 amPDX - ORD

Nonstop4h 07mHawaiian Airlines

Mon 5/1211:00 amORD - PDX

1 stop7h 48mHawaiian Airlines

Deal found 4/21

$422

Thu 5/12:43 pmBOI - ORD

1 stop7h 24mUnited Airlines

Fri 5/29:04 amORD - BOI

Nonstop4h 10mUnited Airlines

Deal found 4/22

$429

Thu 5/19:35 amPDX - ORD

1 stop6h 26mAlaska Airlines

Mon 5/122:07 pmORD - PDX

Nonstop4h 33mAlaska Airlines

Deal found 4/22

$467

Fri 5/26:20 amPDX - MDW

1 stop10h 48mFrontier

Sun 5/46:15 amMDW - PDX

1 stop11h 27mFrontier

Deal found 4/21

$300

Fri 5/211:59 pmPDX - ORD

1 stop9h 08mAmerican Airlines

Sat 5/31:17 pmORD - PDX

1 stop8h 37mAmerican Airlines

Deal found 4/22

$335

Fri 5/21:15 pmPDX - ORD

1 stop13h 55mFrontier

Sun 5/45:45 amORD - PDX

2 stops35h 57mFrontier

Deal found 4/21

$357

One-way flights from Oregon to Chicago
Search for one-way flight options from Oregon to Chicago. Find affordable one-way fares based on user searches. Data last updated April 22, 2025.

Thu 8/141:10 pmBOI - MDW

Nonstop3h 25mSouthwest

Deal found 4/22

$78

Fri 7/412:39 pmBOI - ORD

Nonstop3h 26mUnited Airlines

Deal found 4/22

$78

Tue 5/132:41 pmBOI - ORD

1 stop8h 18mAlaska Airlines

Deal found 4/21

$87

Fri 6/2011:40 pmBOI - MDW

1 stop9h 01mDelta

Deal found 4/21

$88

Wed 6/46:00 amBOI - ORD

1 stop5h 43mDelta

Deal found 4/22

$88

Thu 5/2212:36 pmBOI - MDW

1 stop7h 17mFrontier

Deal found 4/21

$99

Thu 5/2912:36 pmBOI - ORD

1 stop10h 16mFrontier

Deal found 4/22

$105

Wed 7/165:35 pmPDX - ORD

Nonstop4h 04mAlaska Airlines

Deal found 4/22

$114

Sat 6/72:30 pmPDX - MDW

Nonstop3h 55mSouthwest

Deal found 4/22

$114

Sat 6/76:35 amPDX - MDW

1 stop12h 18mFrontier

Deal found 4/22

$115

Wed 10/89:50 amBOI - ORD

1 stop9h 09mHawaiian Airlines

Deal found 4/21

$117

Sat 5/175:51 pmPDX - ORD

Nonstop4h 05mHawaiian Airlines

Deal found 4/21

$119

Cheapflights Fare Finder

Use the filters below to find and compare flights from Oregon to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Wed 7/2

10:24 am-5:40 pm

1 stop6h 16m

Chicago Midway

Mon 7/7

9:20 am-2:00 pm

1 stop5h 40m

$175

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Sat 5/24

12:50 pm-9:40 pm

1 stop7h 50m

Chicago O'Hare Intl

Thu 5/29

1:40 pm-6:21 pm

1 stop5h 41m

$175

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Fri 6/27

5:42 pm-12:30 am

1 stop5h 48m

Chicago O'Hare Intl

Mon 6/30

8:45 am-11:43 am

Nonstop3h 58m

$201

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Fri 7/4

1:30 pm-8:55 pm

1 stop6h 25m

Chicago Midway

Fri 7/11

10:30 am-1:05 pm

Nonstop3h 35m

$205

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 5/21

1:02 pm-11:56 pm

1 stop8h 54m

Chicago O'Hare Intl

Wed 5/28

7:00 am-12:22 pm

1 stop7h 22m

$234

PortlandChicago

PDX - ORD

PDXORD

Portland

Sun 5/11

5:40 pm-8:55 am

2 stops13h 15m

Chicago O'Hare Intl

Fri 5/16

5:21 pm-12:38 am

1 stop9h 17m

$236

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 6/5

5:51 pm-11:56 pm

Nonstop4h 05m

Chicago O'Hare Intl

Tue 6/10

7:00 am-9:23 am

Nonstop4h 23m

$238

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 5/15

6:20 am-7:08 pm

1 stop10h 48m

Chicago Midway

Sun 5/18

6:15 am-3:42 pm

1 stop11h 27m

$238

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 5/22

5:40 pm-10:55 am

1 stop15h 15m

Chicago O'Hare Intl

Tue 5/27

9:14 pm-12:42 pm

2 stops17h 28m

$239

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 5/21

12:30 pm-9:40 pm

1 stop7h 10m

Chicago O'Hare Intl

Wed 5/28

1:40 pm-10:56 pm

2 stops11h 16m

$240

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 60 results

...

Best time to book a flight from Oregon to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Oregon 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 Oregon to Chicago

What is the cheapest month to book a flight from Oregon to Chicago?

Currently, August is the cheapest month in which you can book a flight from Oregon to Chicago (average of $245). Flying from Oregon to Chicago in March is currently the most expensive (average of $321). 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 OR to CHI?

When flying from Oregon to Chicago, 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 Oregon to Chicago

The most flights from USOR to CHI are scheduled on a Tuesday (25 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (13 on average).

Rainfall in Chicago by month

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

If weather is an important factor for your trip to Chicago, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta from Oregon to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Alaska Airlines

8.0

Very good

9,906 reviews

Reviews

1 / 20

4.0

Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Alaska Airlines

8.0

Very good

9,906 reviews

Alaska Airlines

8.0

Very good

9,906 reviews

Reviews

1 / 20

4.0

Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Southwest

8.0

Very good

4,287 reviews

Alaska Airlines

8.0

Very good

9,906 reviews

Reviews

1 / 20

4.0

Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Delta

8.0

Very good

7,920 reviews

Alaska Airlines

8.0

Very good

9,906 reviews

Reviews

1 / 20

4.0

Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Hawaiian Airlines

7.9

Good

2,392 reviews

Alaska Airlines

8.0

Very good

9,906 reviews

Reviews

1 / 20

4.0

Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

United Airlines

7.4

Good

8,684 reviews

Alaska Airlines

8.0

Very good

9,906 reviews

Reviews

1 / 20

4.0

Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Related info for your journey

What are the cheapest airlines to fly from Oregon to Chicago one-way?
To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $78. United Airlines flights start at $78 while deals on Alaska Airlines start at $87 one-way.
What are the most popular routes from Oregon to Chicago?
The most popular route from Oregon to Chicago is Portland - Chicago O'Hare Intl. You may also consider Portland - Chicago Midway or Boise Air Term. Gowen Fld - Chicago O'Hare Intl.
What are the most reliable airlines from Oregon to Chicago?
The top 3 most reliable airlines when flying from Oregon to Chicago are SWISS (95%), Brussels Airlines (90%) and Lufthansa (82%).
What are the cheapest flights from Oregon to Chicago?
Looking for the cheapest flight from Oregon to Chicago? While on average our users pay $949, our data indicates the cheapest price to be $120. The most popular route (Portland - Chicago O'Hare Intl), is priced around $156.
Can I find deals for flights from Oregon to Chicago that include hotel bookings?
Yes. In addition to deals on Oregon to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Oregon to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oregon to Chicago.
Can I find deals for business class flights from Oregon to Chicago?
Yes. Cheapflights offers flight deals from Oregon to Chicago 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 Oregon to Chicago?
Currently, August is the cheapest month in which you can book a flight from Oregon to Chicago (average of $245). Flying from Oregon to Chicago in March is currently the most expensive (average of $321). 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

Merrillville

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Porter

Lansing

Valparaiso

Chesterton

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Top 8 airlines flying from Oregon to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$82	Average$132	FlexibilityNo cancel fee	On-time65%
Frontier	Cheapest$108	Average$212	FlexibilityNo cancel fee	On-time62%
Delta	Cheapest$123	Average$393	FlexibilityNo cancel fee	On-timeN/A
Alaska Airlines	Cheapest$185	Average$483	FlexibilityNo cancel fee	On-time75%
American Airlines	Cheapest$193	Average$421	FlexibilityNo cancel fee	On-time71%
Hawaiian Airlines	Cheapest$202	Average$362	FlexibilityNo cancel fee	On-time85%
United Airlines	Cheapest$214	Average$522	FlexibilityNo cancel fee	On-time69%
Southwest	Cheapest$249	Average$445	FlexibilityNo cancel fee	On-time63%

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$78+ Cheap flights from Oregon to Chicago (CHI)

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 8/14. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Oregon to Chicago with Cheapflights

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3. Compare prices and book

Cheap flight deals from Oregon to Chicago

Keep the following information in mind while searching for Oregon to Chicago flight deals. Data was last updated April 22, 2025.

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Oregon to Chicago

Cheapest flights from Oregon to ChicagoExplore the most affordable flight options available from Oregon to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 22, 2025.

Explore the most affordable flight options available from Oregon to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 22, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Oregon to Chicago that are best for you.

Best time to book a flight from Oregon to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Oregon with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Oregon to Chicago

What is the cheapest month to book a flight from Oregon to Chicago?

What is the cheapest time of day to fly from OR to CHI?

Find hourly flight availability from Oregon to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 22, 2025.

Weekly flight availability from Oregon to Chicago

Explore weekly flight availability from Oregon to Chicago. 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 April 22, 2025.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

Reviews of airlines servicing Chicago

Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta from Oregon to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Oregon to Chicago. 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 Oregon to Chicago one-way?

What are the most popular routes from Oregon to Chicago?

What are the most reliable airlines from Oregon to Chicago?

What are the cheapest flights from Oregon to Chicago?

Can I find deals for flights from Oregon to Chicago that include hotel bookings?

How can I find direct flights from Oregon to Chicago?

Can I find deals for business class flights from Oregon to Chicago?

What is the cheapest month to book a flight from Oregon to Chicago?

Traveling to a place near Oregon?

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Oregon to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top 8 airlines flying from Oregon to Chicago

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Cheapest flights from Oregon to Chicago
Explore the most affordable flight options available from Oregon to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 22, 2025.