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$122+ 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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
Aug 31 — Sep 71
Mon 8/31
Mon 9/7
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 August 1, 2026.

This Frontier deal was found by Cheapflights users on 7/28. 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.
Thu 8/2012:24 pm
BOI
-
ORD
1 stop24h 12m
Frontier
Wed 8/262:41 pm
ORD
-
BOI
1 stop21h 48m
Frontier
Deal found 7/28$253
This CheapOair deal was found by Cheapflights users on 7/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/142:50 pm
BOI
-
ORD
1 stop13h 48m
Frontier
Wed 9/161:21 pm
ORD
-
BOI
1 stop25h 34m
Frontier
Deal found 7/29$259
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/93:52 pm
BOI
-
ORD
1 stop12h 50m
Frontier
Mon 10/126:50 am
ORD
-
BOI
1 stop9h 07m
Frontier
Deal found 7/30$267
This Frontier deal was found by Cheapflights users on 7/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/163:52 pm
BOI
-
ORD
1 stop12h 50m
Frontier
Sun 11/17:00 am
ORD
-
BOI
1 stop8h 57m
Frontier
Deal found 7/27$269
This CheapOair deal was found by Cheapflights users on 7/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:50 pm
BOI
-
ORD
1 stop13h 48m
Frontier
Sun 9/138:55 pm
ORD
-
BOI
1 stop18h 00m
Frontier
Deal found 7/27$274
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
Mon 9/282:50 pm
BOI
-
ORD
1 stop13h 48m
Frontier
Wed 9/306:30 am
ORD
-
BOI
2 stops32h 25m
Frontier
Deal found 7/28$289
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/132:50 pm
BOI
-
ORD
1 stop13h 48m
Frontier
Wed 9/161:21 pm
ORD
-
BOI
1 stop25h 34m
Frontier
Deal found 7/29$290
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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.
Sat 9/54:20 pm
BOI
-
ORD
1 stop6h 39m
Alaska Airlines
Wed 9/96:00 am
ORD
-
BOI
1 stop7h 35m
Alaska Airlines
Deal found 7/28$293
This Expedia deal was found by Cheapflights users on 7/29. 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.
Fri 10/237:20 am
BOI
-
ORD
1 stop10h 33m
Multiple Airlines
Mon 10/266:50 am
ORD
-
BOI
1 stop9h 07m
Multiple Airlines
Deal found 7/29$302
This CheapOair deal was found by Cheapflights users on 7/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/111:24 pm
BOI
-
ORD
1 stop6h 28m
Frontier
Sat 8/159:57 pm
ORD
-
BOI
1 stop15h 32m
Frontier
Deal found 7/27$304
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/212:50 pm
BOI
-
ORD
1 stop13h 48m
Frontier
Thu 9/248:55 pm
ORD
-
BOI
1 stop18h 00m
Frontier
Deal found 7/29$306
This Frontier deal was found by Cheapflights users on 7/28. 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.
Thu 10/159:34 pm
PDX
-
ORD
1 stop12h 23m
Frontier
Mon 10/1911:06 am
ORD
-
PDX
1 stop7h 29m
Frontier
Deal found 7/28$320

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 August 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$253
(Frontier)

One-way from

$122
(Frontier)

Popular in

November

Cheapest in

January

Average price

$373

Good round-trip deal

$355 or less

Good one-way deal

$211 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. 7% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 August 1, 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

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Wed 9/9

4:20 pm-11:59 pm

1 stop6h 39m

Chicago O'Hare Intl

Sat 9/19

6:00 am-12:35 pm

1 stop7h 35m

$293
Quickest round-trip

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Wed 10/28

12:37 pm-5:10 pm

Nonstop3h 33m

Chicago O'Hare Intl

Sat 10/31

7:45 pm-10:51 pm

Nonstop4h 06m

$313

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Sat 9/19

4:20 pm-11:59 pm

1 stop6h 39m

Chicago O'Hare Intl

Wed 9/23

6:00 am-12:35 pm

1 stop7h 35m

$313

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 9/9

10:45 pm-12:20 pm

2 stops11h 35m

Chicago Midway

Tue 9/15

3:50 pm-10:15 pm

1 stop8h 25m

$322

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Fri 10/16

6:04 pm-5:40 am

1 stop10h 36m

Chicago O'Hare Intl

Mon 10/19

6:00 am-12:35 pm

1 stop7h 35m

$322

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Mon 9/14

5:40 pm-11:59 pm

1 stop5h 19m

Chicago O'Hare Intl

Wed 9/16

8:40 am-11:26 am

Nonstop3h 46m

$323

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 9/1

9:45 am-6:19 pm

1 stop6h 34m

Chicago O'Hare Intl

Fri 9/4

1:50 pm-9:44 pm

1 stop9h 54m

$327

PortlandChicago

PDX - MDW

PDXMDW

Portland

Mon 9/28

12:25 am-8:48 am

1 stop6h 23m

Chicago Midway

Thu 10/15

5:31 pm-11:44 pm

1 stop8h 13m

$327

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Wed 10/28

12:55 pm-9:00 pm

1 stop7h 05m

Chicago Midway

Thu 10/29

5:40 am-11:20 am

1 stop6h 40m

$328

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Mon 9/14

2:55 pm-11:50 pm

1 stop7h 55m

Chicago Midway

Wed 9/16

3:50 pm-11:15 pm

1 stop8h 25m

$333

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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, January is the cheapest month in which you can book a flight from Oregon to Chicago (average of $290). Flying from Oregon to Chicago in June is currently the most expensive (average of $409). 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 August 1, 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 33% versus a flight at noon.

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 August 1, 2026.

The most flights from USOR to CHI are scheduled on a Friday (34 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (12 on average).

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

Airfare is typical for this route at the moment.
Oregon to Chicago flights typically cost between $291 and $488 in October.
The cheapest round-trip price found within the last 5 days was $320 on Frontier (Oct 15-Oct 19).

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 29 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 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 August 1, 2026.

Travelers seeking maximum savings on their Oregon to Chicago flight should consider departing on Saturday at noon 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.

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 33m. Airlines will cover a distance of 1432 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. Alaska Airlines flights start at $108 while deals on American Airlines start at $108 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 Qatar Airways (88%), Alaska Airlines (88%) and SWISS (85%).

  • What are the cheapest flights from Oregon to Chicago?

    Looking for the cheapest flight from Oregon to Chicago? While on average our users pay $1,220, our data indicates the cheapest price to be $158. The most popular route (Portland - Chicago O'Hare Intl), is priced around $278.

  • 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, January is the cheapest month in which you can book a flight from Oregon to Chicago (average of $290). Flying from Oregon to Chicago in June is currently the most expensive (average of $409). 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
Valparaiso
Hammond
Saint Joseph
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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Dallas/Fort Worth to Midway flights
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Atlanta to Midway flights
Dulles Intl to O'Hare Intl flights
Tampa to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Miami to O'Hare Intl flights
Philadelphia to Midway flights
Dulles Intl to Midway flights
Minneapolis to O'Hare Intl flights
LaGuardia to Midway flights
Baltimore to Midway flights
Los Angeles to Midway flights
Raleigh to O'Hare Intl flights
Austin to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Minneapolis to Midway flights
Charlotte to O'Hare Intl flights
San Diego to O'Hare Intl flights
Portland to O'Hare Intl flights
Denver to Midway flights
Salt Lake City to O'Hare Intl flights
New Orleans to O'Hare Intl flights
San Francisco to Midway flights
Hobby to Midway flights
LaGuardia to St. Louis flights
Seattle to Midway flights
Newark to St. Louis flights
Detroit to O'Hare Intl flights
Las Vegas to O'Hare Intl 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 August 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$86Average$238FlexibilityNo cancel feeOn-time62%
Hawaiian AirlinesCheapest$93Average$271FlexibilityNo cancel feeOn-time85%
DeltaCheapest$108Average$394FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$195Average$353FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$198Average$424FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$227Average$357FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$231Average$423FlexibilityNo cancel feeOn-time69%

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