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$65+ 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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$183
(Delta)

One-way from

$65
(FlightHub)

Popular in

March

Cheapest in

January

Average price

$346

Good round-trip deal

$394 or less

Good one-way deal

$201 or less
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Portland-Chicago (CHI) flights.
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From Oregon to Chicago (CHI)
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One-way flight from Oregon to Chicago (CHI)
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Highest demand for flights based on searches. 6% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from Oregon to Chicago (CHI).
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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 February 20, 2025.

This Delta deal was found by Cheapflights users on 2/20. 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 4/225:00 amEUG - ORD
1 stop6h 19mDelta
Tue 4/297:50 amORD - EUG
1 stop9h 25mDelta
Deal found 2/20$183
This Delta deal was found by Cheapflights users on 2/20. 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.
Sun 4/204:40 pmBOI - ORD
1 stop6h 19mDelta
Sat 5/37:45 amORD - BOI
1 stop7h 45mDelta
Deal found 2/20$206
This Mytrip deal was found by Cheapflights users on 2/20. 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.
Mon 4/76:41 pmMFR - ORD
2 stops33h 52mMultiple Airlines
Wed 4/92:58 pmORD - MFR
1 stop23h 13mMultiple Airlines
Deal found 2/20$219
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Tue 3/111:31 pmBOI - ORD
1 stop16h 11mSpirit Airlines
Sun 3/167:47 amORD - BOI
1 stop29h 45mSpirit Airlines
Deal found 2/19$222
This Delta deal was found by Cheapflights users on 2/19. 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 4/85:30 amBOI - MDW
1 stop7h 47mDelta
Sat 4/127:13 pmMDW - BOI
1 stop5h 36mDelta
Deal found 2/19$229
This Delta deal was found by Cheapflights users on 2/20. 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 4/112:59 amPDX - ORD
1 stop5h 50mDelta
Wed 4/91:45 pmORD - PDX
1 stop6h 25mDelta
Deal found 2/20$237
This Delta deal was found by Cheapflights users on 2/20. 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 4/226:20 amPDX - MDW
1 stop6h 02mDelta
Sat 4/261:16 pmMDW - PDX
1 stop9h 23mDelta
Deal found 2/20$237
This United Airlines deal was found by Cheapflights users on 2/20. 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 3/177:21 pmPDX - ORD
1 stop8h 56mUnited Airlines
Wed 3/197:59 pmORD - PDX
Nonstop4h 40mUnited Airlines
Deal found 2/20$238
This Expedia deal was found by Cheapflights users on 2/20. 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.
Wed 4/1610:04 amPDX - ORD
1 stop12h 33mMultiple Airlines
Sun 4/203:16 pmORD - PDX
Nonstop4h 34mMultiple Airlines
Deal found 2/20$239
This CheapOair deal was found by Cheapflights users on 2/20. 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.
Fri 2/216:32 amPDX - ORD
1 stop16h 12mFrontier
Tue 3/116:45 amORD - PDX
1 stop19h 52mFrontier
Deal found 2/20$240
This CheapOair deal was found by Cheapflights users on 2/20. 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 4/36:40 amPDX - MDW
1 stop15h 41mFrontier
Sun 4/68:50 pmMDW - PDX
1 stop13h 57mFrontier
Deal found 2/20$240
This FlightHub deal was found by Cheapflights users on 2/20. 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.
Sun 3/306:50 pmPDX - ORD
1 stop9h 52mSpirit Airlines
Wed 4/22:34 pmORD - PDX
1 stop29h 21mSpirit Airlines
Deal found 2/20$242

Find flights from Oregon to Chicago within your budget

Customize your flight search to find flights from Oregon to Chicago 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 February 20, 2025.

Fly from

Oregon

Fly to

Chicago

Route

Depart

Return

Price

EugeneChicago

EUG - ORD

EUGORD

Eugene

Tue 4/22

5:00 am-1:19 pm

1 stop6h 19m

Chicago O'Hare Intl

Tue 4/29

7:50 am-3:15 pm

1 stop9h 25m

$183

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Sun 4/20

4:40 pm-11:59 pm

1 stop6h 19m

Chicago O'Hare Intl

Sat 5/3

7:45 am-2:30 pm

1 stop7h 45m

$206

MedfordChicago

MFR - ORD

MFRORD

Medford

Mon 4/7

6:41 pm-6:33 am

2 stops33h 52m

Chicago O'Hare Intl

Wed 4/9

2:58 pm-12:11 pm

1 stop23h 13m

$219

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Tue 3/11

1:31 pm-6:42 am

1 stop16h 11m

Chicago O'Hare Intl

Sun 3/16

7:47 am-12:32 pm

1 stop29h 45m

$222

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Tue 4/8

5:30 am-2:17 pm

1 stop7h 47m

Chicago Midway

Sat 4/12

7:13 pm-11:49 pm

1 stop5h 36m

$229

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 4/1

12:59 am-8:49 am

1 stop5h 50m

Chicago O'Hare Intl

Wed 4/9

1:45 pm-6:10 pm

1 stop6h 25m

$237

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 4/22

6:20 am-2:22 pm

1 stop6h 02m

Chicago Midway

Sat 4/26

1:16 pm-8:39 pm

1 stop9h 23m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 3/17

7:21 pm-6:17 am

1 stop8h 56m

Chicago O'Hare Intl

Wed 3/19

7:59 pm-10:39 pm

Nonstop4h 40m

$238

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 4/16

10:04 am-12:37 am

1 stop12h 33m

Chicago O'Hare Intl

Sun 4/20

3:16 pm-5:50 pm

Nonstop4h 34m

$239

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 4/3

6:40 am-12:21 am

1 stop15h 41m

Chicago Midway

Sun 4/6

8:50 pm-8:47 am

1 stop13h 57m

$240

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 60 results
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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.

Travel insights for flights from Oregon to Chicago

Get recent, data-driven insights about flights from Oregon to Chicago including ideal travel times, pricing trends, and more.

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?

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 February 20, 2025.

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

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 February 20, 2025.

The most flights from USOR to CHI are scheduled on a Thursday (15 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 on average).

Rainfall in Chicago by month

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

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

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated February 20, 2025.
Read reviews from past customers who have flown Southwest, Alaska Airlines 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.
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Hawaiian Airlines
7.9
Good
2,317 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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?

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $65. Frontier flights start at $76 while deals on Delta start at $97 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 Brussels Airlines (97%), SWISS (97%) and Lufthansa (95%).

  • What are the cheapest flights from Oregon to Chicago?

    Looking for the cheapest flight from Oregon to Chicago? While on average our users pay $1,013, our data indicates the cheapest price to be $127. The most popular route (Portland - Chicago O'Hare Intl), is priced around $129.

  • 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

Traveling to a place near Oregon?

Book flights to Oregon if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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.
John F Kennedy Intl to O'Hare Intl flights
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Boston to O'Hare Intl flights
Seattle to O'Hare Intl flights
Baltimore to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Newark to Midway flights
John F Kennedy Intl to Midway flights
Philadelphia to O'Hare Intl flights
Denver to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
LaGuardia to Midway flights
Los Angeles to Midway flights
Baltimore to Midway flights
Austin to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Ontario to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Reagan-National to Midway flights
Raleigh to O'Hare Intl flights
Burbank to O'Hare Intl flights
San Diego to O'Hare Intl flights
Dulles Intl to Midway flights
Charlotte to O'Hare Intl flights
San Francisco to Midway flights
Orlando to O'Hare Intl flights
Love Field to O'Hare Intl flights
Miami to O'Hare Intl flights
Seattle to Midway flights
Atlanta to Midway flights
Newark to St. Louis flights
Portland to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Minneapolis to Midway flights
LaGuardia to St. Louis flights
Philadelphia to Midway flights
Tampa to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Hobby to O'Hare Intl flights
Oakland to O'Hare Intl flights
Dulles Intl to St. Louis flights
Denver to Midway flights

Top 7 airlines flying from Oregon to Chicago

Discover the top 7 airlines that operate flights from Oregon to Chicago. 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$82Average$135FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$240FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$178Average$483FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$189Average$440FlexibilityNo cancel feeOn-time71%
DeltaCheapest$207Average$402FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$218Average$536FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$246Average$426FlexibilityNo cancel feeOn-time63%
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