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$71+ 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
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 octubre 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$220
(Kiwi.com)

One-way from

$71
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$339

Good round-trip deal

$334 or less

Good one-way deal

$177 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. 9% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in October 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 octubre 30, 2025.

This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/612:52 pmPDX - ORD
1 stop9h 23mFrontier
jue. 12/47:00 amORD - PDX
1 stop6h 56mFrontier
Deal found 10/28$226
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/102:31 pmPDX - ORD
1 stop7h 19mAlaska Airlines
mar. 12/162:05 pmORD - PDX
Nonstop4h 43mAlaska Airlines
Deal found 10/28$227
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.
mar. 11/41:26 pmPDX - ORD
1 stop24h 13mFrontier
lun. 11/247:00 amORD - PDX
1 stop10h 16mFrontier
Deal found 10/28$228
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.
mar. 11/111:26 pmPDX - ORD
1 stop24h 13mFrontier
vie. 11/1410:43 pmORD - PDX
2 stops39h 13mFrontier
Deal found 10/28$229
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/73:26 pmPDX - ORD
1 stop6h 49mFrontier
mié. 11/126:05 pmORD - PDX
1 stop19h 51mFrontier
Deal found 10/28$230
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.
lun. 12/85:32 pmPDX - ORD
1 stop10h 32mMultiple Airlines
lun. 12/156:50 amORD - PDX
1 stop11h 47mMultiple Airlines
Deal found 10/28$231
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.
sáb. 11/1512:52 pmPDX - ORD
1 stop8h 37mFrontier
mié. 11/196:05 pmORD - PDX
2 stops45h 03mFrontier
Deal found 10/30$233
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/73:26 pmPDX - ORD
1 stop6h 49mFrontier
dom. 11/96:00 amORD - PDX
1 stop7h 56mFrontier
Deal found 10/28$234
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.
sáb. 12/139:48 amPDX - ORD
1 stop12h 25mFrontier
dom. 12/145:13 pmORD - PDX
2 stops17h 23mFrontier
Deal found 10/28$235
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.
dom. 12/2111:00 pmPDX - ORD
Nonstop4h 02mAlaska Airlines
lun. 1/57:00 amORD - PDX
Nonstop4h 50mAlaska Airlines
Deal found 10/30$236
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/510:50 amPDX - ORD
Nonstop4h 02mUnited Airlines
lun. 12/87:37 pmORD - PDX
Nonstop4h 38mUnited Airlines
Deal found 10/29$237
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/512:32 amPDX - MDW
1 stop6h 47mDelta
sáb. 12/131:50 pmMDW - PDX
1 stop9h 02mDelta
Deal found 10/28$237

Cheapflights Fare Finder

 
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 octubre 30, 2025.
Use the filters below to find and compare flights from Oregon to Chicago that are best for you.

Fly from

Oregon

Fly to

Chicago

Route

Depart

Return

Price

PortlandChicago

PDX - ORD

PDXORD

Portland

mié. 12/10

11:59 pm-5:52 am

Nonstop3h 53m

Chicago O'Hare Intl

lun. 12/15

7:37 pm-10:15 pm

Nonstop4h 38m

$227

PortlandChicago

PDX - ORD

PDXORD

Portland

lun. 12/15

12:32 am-8:40 am

1 stop6h 08m

Chicago O'Hare Intl

mar. 1/13

6:12 am-12:46 pm

1 stop8h 34m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

mar. 12/9

12:32 am-8:40 am

1 stop6h 08m

Chicago O'Hare Intl

mar. 12/16

6:00 am-12:54 pm

1 stop8h 54m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

jue. 11/27

7:00 am-1:02 pm

Nonstop4h 02m

Chicago O'Hare Intl

jue. 12/4

7:37 pm-10:15 pm

Nonstop4h 38m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

vie. 12/12

12:32 am-10:33 am

1 stop8h 01m

Chicago O'Hare Intl

mar. 12/16

7:20 am-12:40 pm

1 stop7h 20m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

dom. 12/21

11:00 pm-5:02 am

Nonstop4h 02m

Chicago O'Hare Intl

dom. 1/11

3:49 pm-10:45 pm

1 stop8h 56m

$247

PortlandChicago

PDX - ORD

PDXORD

Portland

sáb. 1/10

1:53 pm-9:42 pm

1 stop5h 49m

Chicago O'Hare Intl

lun. 1/12

7:30 am-12:44 pm

1 stop7h 14m

$247

PortlandChicago

PDX - ORD

PDXORD

Portland

vie. 1/9

5:23 am-1:22 pm

1 stop5h 59m

Chicago O'Hare Intl

mié. 1/14

2:49 pm-10:15 pm

1 stop9h 26m

$247

PortlandChicago

PDX - ORD

PDXORD

Portland

dom. 1/11

1:30 pm-11:53 pm

1 stop8h 23m

Chicago O'Hare Intl

mié. 1/14

2:49 pm-10:15 pm

1 stop9h 26m

$247

PortlandChicago

PDX - MDW

PDXMDW

Portland

jue. 12/4

12:32 am-9:19 am

1 stop6h 47m

Chicago Midway

mar. 12/9

1:50 pm-8:52 pm

1 stop9h 02m

$247

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

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.

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 $120). Flying from Oregon to Chicago in March is currently the most expensive (average of $256). 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 octubre 30, 2025.

When flying from Oregon to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 20% versus a flight in the morning.

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

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

Travelers seeking maximum savings on their Oregon to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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.

  • How long is the flight from Oregon to Chicago?

    Departing from Oregon to Chicago will take you 3h 53m. Airlines will cover a distance of 1733 mi. This flight may include one or multiple stops.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $91. Alaska Airlines flights start at $114 while deals on United Airlines start at $114 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 (92%), SWISS (82%) and Alaska Airlines (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 $914, our data indicates the cheapest price to be $118. The most popular route (Portland - Chicago O'Hare Intl), is priced around $185.

  • 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 $120). Flying from Oregon to Chicago in March is currently the most expensive (average of $256). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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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.
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Newark to Midway flights
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Newark to St. Louis flights
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Philadelphia to Midway flights
Charlotte to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
San Francisco to Midway flights
George Bush Intcntl to O'Hare Intl flights
Dulles Intl to Midway flights
Hobby to O'Hare Intl flights
Tampa to O'Hare Intl flights
Miami to O'Hare Intl flights
Minneapolis to Midway flights
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Santa Ana to O'Hare Intl flights
John F Kennedy Intl to St. Louis flights
Reagan-National to Midway flights
Austin to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Love Field to O'Hare Intl flights
Hartford to O'Hare Intl flights
Orlando to O'Hare Intl flights
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Portland to O'Hare Intl flights
LaGuardia to St. Louis flights
Boston to Midway flights

Top 8 airlines flying from Oregon to Chicago

Discover the top 8 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 octubre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$94Average$280FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$119Average$194FlexibilityNo cancel feeOn-time65%
DeltaCheapest$123Average$361FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$125Average$324FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$194Average$429FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$197Average$383FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$224Average$427FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$246Average$427FlexibilityNo cancel feeOn-time63%

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