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$105+ 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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
Apr 18 — Apr 251
Sat 4/18
Sat 4/25
1 adult, Economy
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Cheap 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 March 19, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/14. 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 4/1512:28 pm
PDX
-
ORD
2 stops19h 55m
Multiple Airlines
Wed 5/69:42 pm
ORD
-
PDX
1 stop21h 04m
Multiple Airlines
Deal found 3/14$219
This Super.com deal was found by Cheapflights users on 3/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/179:54 am
PDX
-
ORD
1 stop17h 56m
Frontier
Wed 4/227:21 pm
ORD
-
PDX
1 stop18h 29m
Frontier
Deal found 3/14$221
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 4/1512:28 pm
PDX
-
ORD
1 stop19h 22m
Frontier
Sat 5/27:21 pm
ORD
-
PDX
1 stop18h 29m
Frontier
Deal found 3/14$222
This Booking.com deal was found by Cheapflights users on 3/14. 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.
Thu 4/169:54 am
PDX
-
ORD
1 stop17h 56m
Frontier
Fri 4/1710:55 am
ORD
-
PDX
1 stop26h 47m
Frontier
Deal found 3/14$223
This Kiwi.com deal was found by Cheapflights users on 3/15. 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 5/212:27 pm
PDX
-
ORD
2 stops15h 41m
Frontier
Wed 5/69:42 pm
ORD
-
PDX
1 stop21h 04m
Frontier
Deal found 3/15$224
This Mytrip deal was found by Cheapflights users on 3/15. 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.
Sat 4/1812:27 pm
PDX
-
ORD
1 stop19h 18m
Frontier
Sat 4/257:21 pm
ORD
-
PDX
1 stop18h 29m
Frontier
Deal found 3/15$225
This Kiwi.com deal was found by Cheapflights users on 3/16. 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 4/2912:38 pm
PDX
-
ORD
2 stops21h 35m
Frontier
Wed 5/69:42 pm
ORD
-
PDX
1 stop21h 04m
Frontier
Deal found 3/16$230
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 4/1512:28 pm
PDX
-
ORD
1 stop19h 22m
Frontier
Sat 4/187:21 pm
ORD
-
PDX
1 stop18h 29m
Frontier
Deal found 3/14$233
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 4/2512:27 pm
PDX
-
ORD
2 stops15h 53m
Frontier
Wed 5/69:42 pm
ORD
-
PDX
1 stop21h 04m
Frontier
Deal found 3/17$237
This Kiwi.com deal was found by Cheapflights users on 3/14. 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.
Tue 4/141:48 pm
PDX
-
ORD
2 stops25h 12m
Frontier
Mon 4/2010:55 am
ORD
-
PDX
1 stop26h 57m
Frontier
Deal found 3/14$238
This Southwest deal was found by Cheapflights users on 3/18. 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.
Sat 5/211:55 pm
PDX
-
MDW
Nonstop3h 55m
Southwest
Sat 5/96:05 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Deal found 3/18$251
This Alaska Airlines deal was found by Cheapflights users on 3/16. 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 4/145:41 pm
EUG
-
ORD
1 stop18h 40m
Alaska Airlines
Tue 4/218:00 am
ORD
-
EUG
1 stop12h 40m
Alaska Airlines
Deal found 3/16$257

Find flight deals from Oregon to Chicago

Keep the following information in mind while searching for Oregon to Chicago flight deals. Data was last updated March 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$219
(Kiwi.com)

One-way from

$105
(Frontier)

Popular in

November

Cheapest in

January

Average price

$389

Good round-trip deal

$304 or less

Good one-way deal

$168 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. 11% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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).
Search Deals

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 March 19, 2026.
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

Cheapest round-trip

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 4/21

2:30 pm-8:34 pm

Nonstop4h 04m

Chicago O'Hare Intl

Wed 4/22

8:00 pm-10:34 pm

Nonstop4h 34m

$251

EugeneChicago

EUG - ORD

EUGORD

Eugene

Tue 4/14

5:41 pm-2:21 pm

1 stop18h 40m

Chicago O'Hare Intl

Tue 4/21

4:10 pm-10:30 pm

1 stop8h 20m

$257

EugeneChicago

EUG - ORD

EUGORD

Eugene

Wed 5/27

11:20 am-10:55 pm

1 stop9h 35m

Chicago O'Hare Intl

Mon 6/1

6:15 pm-10:45 pm

1 stop6h 30m

$257

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Tue 4/28

5:20 pm-5:00 am

1 stop9h 40m

Chicago Midway

Tue 5/5

6:30 am-10:45 am

1 stop6h 15m

$257

EugeneChicago

EUG - ORD

EUGORD

Eugene

Tue 4/14

6:30 am-9:18 pm

2 stops12h 48m

Chicago O'Hare Intl

Tue 4/21

6:00 pm-11:58 pm

1 stop7h 58m

$262

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Wed 5/27

11:20 am-11:20 pm

2 stops10h 00m

Chicago Midway

Mon 6/1

5:15 pm-10:45 pm

1 stop7h 30m

$262

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 4/15

12:28 pm-9:18 pm

1 stop6h 50m

Chicago O'Hare Intl

Sat 4/18

7:35 am-11:47 am

1 stop6h 12m

$277

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 4/18

2:40 pm-11:05 pm

1 stop6h 25m

Chicago Midway

Sat 4/25

10:15 am-12:35 pm

Nonstop4h 20m

$281

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 5/16

4:15 pm-12:58 am

1 stop6h 43m

Chicago O'Hare Intl

Wed 5/27

7:05 am-9:39 am

Nonstop4h 34m

$288

EugeneChicago

EUG - ORD

EUGORD

Eugene

Tue 4/14

6:30 am-9:18 pm

2 stops12h 48m

Chicago O'Hare Intl

Fri 4/17

7:00 am-5:04 pm

2 stops12h 04m

$298

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/18

Showing 1-10 of 60 resultsSorted by cheapest first
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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, December is the cheapest month in which you can book a flight from Oregon to Chicago (average of $120). Flying from Oregon to Chicago in November is currently the most expensive (average of $237). 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 March 19, 2026.

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 afternoon, which can drop the price by up to 37% versus a flight at noon.

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 March 14, 2026.

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.

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 March 19, 2026.

The most flights from USOR to CHI are scheduled on a Wednesday (26 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 on average).

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

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 4h 04m. 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 $72. Spirit Airlines flights start at $79 while deals on Southwest start at $85 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 Boise Air Term. Gowen Fld - Chicago O'Hare Intl or Portland - Chicago Midway.

  • What are the most reliable airlines from Oregon to Chicago?

    The top 3 most reliable airlines when flying from Oregon to Chicago are Lufthansa (95%), Brussels Airlines (93%) and American Airlines (92%).

  • What are the cheapest flights from Oregon to Chicago?

    Looking for the cheapest flight from Oregon to Chicago? While on average our users pay $917, our data indicates the cheapest price to be $113. The most popular route (Portland - Chicago O'Hare Intl), is priced around $251.

  • 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, December is the cheapest month in which you can book a flight from Oregon to Chicago (average of $120). Flying from Oregon to Chicago in November is currently the most expensive (average of $237). 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
Lansing
Merrillville
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.
John F Kennedy Intl to O'Hare Intl flights
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Ontario to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Orlando to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Dulles Intl to Midway flights
LaGuardia to Midway flights
Atlanta to Midway flights
Austin to O'Hare Intl flights
Baltimore to Midway flights
Hobby to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Newark to Midway flights
Tampa to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Los Angeles to Midway flights
San Diego to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Newark to St. Louis flights
Raleigh to O'Hare Intl flights
San Francisco to Midway flights
Boston to Midway flights
Burbank to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Minneapolis to Midway flights
LaGuardia to St. Louis flights
San Jose to O'Hare Intl flights
Sacramento to O'Hare Intl flights
Hartford to O'Hare Intl flights
Dallas/Fort Worth to St. Louis flights
John F Kennedy Intl to St. Louis flights
Love Field to O'Hare Intl flights
Miami to O'Hare Intl flights
Reagan-National to Midway flights
Nashville to O'Hare Intl 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 March 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$93Average$184FlexibilityNo cancel feeOn-time65%
FrontierCheapest$96Average$238FlexibilityNo cancel feeOn-time62%
DeltaCheapest$99Average$352FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$125Average$317FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$176Average$311FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$179Average$411FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$201Average$405FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$209Average$395FlexibilityNo cancel feeOn-time75%

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