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$94+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
ene. 22 — ene. 291
mié. 1/22
mié. 1/29
1 adult, Economy
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Cheap flight deals from Oregon to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Oregon (USOR) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated enero 17, 2025.

Round-trip from

$227
(American Airlines)

One-way from

$97
(Priceline)
From Oregon to Chicago (CHI)
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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 enero 17, 2025.

This Alaska Airlines deal was found by Cheapflights users on 1/16. 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.
sáb. 9/1311:00 pmPDX - ORD
Nonstop4h 04mAlaska Airlines
mié. 9/177:00 amORD - PDX
Nonstop4h 34mAlaska Airlines
Deal found 1/16$227
This FlightHub deal was found by Cheapflights users on 1/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 1/3112:03 pmPDX - ORD
1 stop10h 29mMultiple Airlines
lun. 2/310:47 pmORD - PDX
1 stop19h 48mMultiple Airlines
Deal found 1/15$228
This Booking.com deal was found by Cheapflights users on 1/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 1/2612:03 pmPDX - ORD
1 stop24h 08mFrontier
jue. 1/306:36 pmORD - PDX
1 stop17h 09mFrontier
Deal found 1/16$230
This Booking.com deal was found by Cheapflights users on 1/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 1/2612:03 pmPDX - MDW
1 stop10h 14mFrontier
dom. 2/27:15 amMDW - PDX
1 stop29h 46mFrontier
Deal found 1/15$230
This Mytrip deal was found by Cheapflights users on 1/15. 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.
lun. 1/275:30 pmPDX - ORD
2 stops25h 30mSpirit Airlines
jue. 1/3010:47 pmORD - PDX
1 stop12h 34mSpirit Airlines
Deal found 1/15$231
This Kissandfly.com deal was found by Cheapflights users on 1/15. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/62:40 pmPDX - MDW
2 stops19h 04mMultiple Airlines
mié. 2/127:05 amMDW - PDX
2 stops19h 51mMultiple Airlines
Deal found 1/15$235
This Southwest deal was found by Cheapflights users on 1/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/208:00 amPDX - MDW
Nonstop3h 55mSouthwest
mar. 2/258:30 amMDW - PDX
Nonstop4h 25mSouthwest
Deal found 1/14$238
This United Airlines deal was found by Cheapflights users on 1/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/127:00 amPDX - ORD
Nonstop4h 01mUnited Airlines
mar. 2/184:15 pmORD - PDX
Nonstop4h 33mUnited Airlines
Deal found 1/16$239
This Delta deal was found by Cheapflights users on 1/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/1011:20 amPDX - ORD
1 stop7h 14mDelta
sáb. 9/201:55 pmORD - PDX
1 stop6h 13mDelta
Deal found 1/16$247
This Delta deal was found by Cheapflights users on 1/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 2/105:30 amBOI - MDW
1 stop6h 12mDelta
mié. 2/126:59 pmMDW - BOI
1 stop5h 59mDelta
Deal found 1/15$249
This Delta deal was found by Cheapflights users on 1/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 2/102:55 pmBOI - ORD
1 stop8h 16mDelta
jue. 2/136:15 amORD - BOI
1 stop8h 50mDelta
Deal found 1/16$249
This Delta deal was found by Cheapflights users on 1/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 2/2412:59 amPDX - MDW
1 stop6h 36mDelta
vie. 2/281:26 pmMDW - PDX
1 stop6h 06mDelta
Deal found 1/16$258

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 enero 17, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PortlandChicago

PDX - ORD

PDXORD

Portland

mié. 4/23

11:55 pm-6:00 am

Nonstop4h 05m

Chicago O'Hare Intl

mar. 4/29

10:05 am-12:32 pm

Nonstop4h 27m

$227

PortlandChicago

PDX - ORD

PDXORD

Portland

vie. 1/31

12:03 pm-12:32 am

1 stop10h 29m

Chicago O'Hare Intl

lun. 2/3

10:47 pm-4:35 pm

1 stop19h 48m

$228

PortlandChicago

PDX - ORD

PDXORD

Portland

dom. 1/26

12:03 pm-2:11 pm

1 stop24h 08m

Chicago O'Hare Intl

jue. 1/30

6:36 pm-9:45 am

1 stop17h 09m

$230

PortlandChicago

PDX - MDW

PDXMDW

Portland

dom. 1/26

12:03 pm-12:17 am

1 stop10h 14m

Chicago Midway

dom. 2/2

7:15 am-11:01 am

1 stop29h 46m

$230

PortlandChicago

PDX - ORD

PDXORD

Portland

lun. 1/27

5:30 pm-9:00 pm

2 stops25h 30m

Chicago O'Hare Intl

jue. 1/30

10:47 pm-9:21 am

1 stop12h 34m

$231

PortlandChicago

PDX - ORD

PDXORD

Portland

sáb. 2/8

6:05 am-2:03 pm

1 stop5h 58m

Chicago O'Hare Intl

sáb. 2/15

4:05 pm-6:44 pm

Nonstop4h 39m

$232

PortlandChicago

PDX - MDW

PDXMDW

Portland

jue. 2/6

2:40 pm-11:44 am

2 stops19h 04m

Chicago Midway

mié. 2/12

7:05 am-12:56 am

2 stops19h 51m

$235

PortlandChicago

PDX - MDW

PDXMDW

Portland

jue. 2/20

8:00 am-1:55 pm

Nonstop3h 55m

Chicago Midway

mar. 2/25

8:30 am-10:55 am

Nonstop4h 25m

$238

PortlandChicago

PDX - ORD

PDXORD

Portland

mié. 2/12

7:00 am-1:01 pm

Nonstop4h 01m

Chicago O'Hare Intl

mar. 2/18

4:15 pm-6:48 pm

Nonstop4h 33m

$239

PortlandChicago

PDX - ORD

PDXORD

Portland

sáb. 2/8

5:15 am-1:30 pm

1 stop6h 15m

Chicago O'Hare Intl

mié. 2/19

2:10 pm-8:50 pm

1 stop8h 40m

$247

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

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 $320). 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 enero 17, 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 enero 17, 2025.

The most flights from USOR to CHI are scheduled on a Thursday (16 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (7 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 enero 17, 2025.
Read reviews from past customers who have flown Spirit Airlines, Alaska Airlines and Southwest 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
4,659 reviews

Entertainment

7.7

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,681 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,511 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,964 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
801 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $97. Frontier flights start at $110 while deals on Alaska 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 (95%), SWISS (95%) and Lufthansa (93%).

  • What are the cheapest flights from Oregon to Chicago?

    Looking for the cheapest flight from Oregon to Chicago? While on average our users pay $1,179, our data indicates the cheapest price to be $128. The most popular route (Portland - Chicago O'Hare Intl), is priced around $142.

  • 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 $320). 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.
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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 enero 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$82Average$135FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$237FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$179Average$482FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$188Average$422FlexibilityNo cancel feeOn-time71%
DeltaCheapest$207Average$396FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$218Average$532FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$233Average$506FlexibilityNo cancel feeOn-time63%
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