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$96+ 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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
May 30 — Jun 61
Sat 5/30
Sat 6/6
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 April 30, 2026.

This Trip.com deal was found by Cheapflights users on 4/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/245:31 pm
PDX
-
ORD
1 stop11h 03m
Frontier
Sat 5/308:46 pm
ORD
-
PDX
1 stop17h 04m
Frontier
Deal found 4/25$280
This Trip.com deal was found by Cheapflights users on 4/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/247:00 am
PDX
-
ORD
Nonstop4h 22m
Multiple Airlines
Sat 5/308:46 pm
ORD
-
PDX
1 stop17h 04m
Multiple Airlines
Deal found 4/25$281
This Super.com deal was found by Cheapflights users on 4/25. 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.
Tue 5/265:46 pm
PDX
-
ORD
1 stop24h 46m
Frontier
Sat 5/308:46 pm
ORD
-
PDX
1 stop17h 04m
Frontier
Deal found 4/25$282
This Expedia deal was found by Cheapflights users on 4/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1010:59 pm
PDX
-
ORD
Nonstop4h 01m
Multiple Airlines
Mon 6/157:20 am
ORD
-
PDX
1 stop12h 04m
Multiple Airlines
Deal found 4/29$288
This Expedia deal was found by Cheapflights users on 4/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:31 pm
PDX
-
ORD
1 stop11h 03m
Multiple Airlines
Tue 6/167:59 pm
ORD
-
PDX
1 stop15h 30m
Multiple Airlines
Deal found 4/26$289
This Frontier deal was found by Cheapflights users on 4/28. 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.
Sun 5/315:31 pm
PDX
-
ORD
1 stop11h 03m
Frontier
Fri 6/197:12 am
ORD
-
PDX
1 stop12h 12m
Frontier
Deal found 4/28$290
This Booking.com deal was found by Cheapflights users on 4/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:31 pm
PDX
-
ORD
1 stop11h 03m
Frontier
Wed 6/39:37 pm
ORD
-
PDX
1 stop21h 09m
Frontier
Deal found 4/27$291
This Super.com deal was found by Cheapflights users on 4/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/175:31 pm
PDX
-
ORD
1 stop11h 08m
Frontier
Wed 5/208:56 pm
ORD
-
PDX
1 stop16h 54m
Frontier
Deal found 4/28$292
This Expedia deal was found by Cheapflights users on 4/25. 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.
Mon 5/185:31 pm
PDX
-
ORD
1 stop11h 08m
Multiple Airlines
Wed 5/272:18 pm
ORD
-
PDX
Nonstop4h 32m
Multiple Airlines
Deal found 4/25$293
This Expedia deal was found by Cheapflights users on 4/25. 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.
Mon 7/2010:59 pm
PDX
-
ORD
Nonstop4h 01m
Multiple Airlines
Mon 7/277:15 am
ORD
-
PDX
1 stop12h 49m
Multiple Airlines
Deal found 4/25$294
This Southwest deal was found by Cheapflights users on 4/27. 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.
Sun 5/2411:55 pm
PDX
-
MDW
Nonstop3h 55m
Southwest
Sat 5/306:05 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Deal found 4/27$305
This Southwest deal was found by Cheapflights users on 4/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:10 am
PDX
-
MDW
Nonstop3h 55m
Southwest
Wed 6/35:35 pm
MDW
-
PDX
1 stop7h 25m
Southwest
Deal found 4/29$315

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 April 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$280
(Trip.com)

One-way from

$96
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$379

Good round-trip deal

$371 or less

Good one-way deal

$143 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 ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 30, 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

Sat 6/6

2:12 pm-8:26 pm

Nonstop4h 14m

Chicago O'Hare Intl

Sat 6/13

7:56 pm-10:31 pm

Nonstop4h 35m

$305

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 6/9

9:20 pm-8:40 am

1 stop9h 20m

Chicago Midway

Tue 6/16

5:35 pm-7:55 pm

Nonstop4h 20m

$315

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 5/28

10:40 pm-4:45 am

Nonstop4h 05m

Chicago O'Hare Intl

Wed 6/3

5:00 am-9:47 am

1 stop6h 47m

$315

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 7/30

10:59 pm-5:00 am

Nonstop4h 01m

Chicago O'Hare Intl

Wed 8/5

7:20 am-9:45 am

Nonstop4h 25m

$316
Quickest round-trip

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 10/8

10:59 pm-4:51 am

Nonstop3h 52m

Chicago O'Hare Intl

Tue 10/13

7:10 am-9:30 am

Nonstop4h 20m

$316

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 6/30

11:40 pm-5:45 am

Nonstop4h 05m

Chicago O'Hare Intl

Sun 7/5

7:00 am-9:34 am

Nonstop4h 34m

$316

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 7/21

11:30 pm-5:20 am

Nonstop3h 50m

Chicago Midway

Thu 7/30

5:00 am-9:55 am

1 stop6h 55m

$322

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 5/26

5:30 am-1:45 pm

1 stop6h 15m

Chicago O'Hare Intl

Tue 6/2

7:12 am-11:37 am

1 stop6h 25m

$325

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 5/27

9:44 am-7:03 pm

1 stop7h 19m

Chicago O'Hare Intl

Mon 6/15

7:20 am-9:45 am

Nonstop4h 25m

$326

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 9/30

3:36 pm-12:58 am

1 stop7h 22m

Chicago O'Hare Intl

Sun 10/4

7:10 am-9:30 am

Nonstop4h 20m

$326

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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

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

To ensure you get the cheapest price possible for a flight from Oregon to Chicago, you should look to book at least 42 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, November is the cheapest month in which you can book a flight from Oregon to Chicago (average of $103). Flying from Oregon to Chicago in July is currently the most expensive (average of $690). 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 April 30, 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 April 25, 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 afternoons 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 April 30, 2026.

The most flights from USOR to CHI are scheduled on a Wednesday (26 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (7 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 01m. 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. Delta flights start at $75 while deals on Spirit Airlines start at $79 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 Brussels Airlines (87%), Lufthansa (85%) and United 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 $846, our data indicates the cheapest price to be $154. The most popular route (Portland - Chicago O'Hare Intl), is priced around $270.

  • 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, November is the cheapest month in which you can book a flight from Oregon to Chicago (average of $103). Flying from Oregon to Chicago in July is currently the most expensive (average of $690). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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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Miami to O'Hare Intl flights
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Newark to St. Louis flights
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Denver to Midway flights
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LaGuardia to St. Louis 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 April 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$93Average$184FlexibilityNo cancel feeOn-time65%
FrontierCheapest$96Average$238FlexibilityNo cancel feeOn-time62%
DeltaCheapest$99Average$349FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$113Average$313FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$170Average$315FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$179Average$387FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$204Average$403FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$207Average$388FlexibilityNo cancel feeOn-time75%

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