HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$98+ 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Oregon to Chicago with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 November 20, 2024.

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 November 20, 2024.

This Kiwi.com deal was found by Cheapflights users on 11/19. 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 11/259:40 pmPDX - ORD
1 stop12h 12mMultiple Airlines
Thu 11/286:00 amORD - PDX
1 stop20h 29mMultiple Airlines
Deal found 11/19$210
This Mytrip deal was found by Cheapflights users on 11/19. 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 12/77:16 pmPDX - ORD
1 stop8h 14mSpirit Airlines
Tue 12/106:35 amORD - PDX
3 stops15h 53mSpirit Airlines
Deal found 11/19$211
This Gotogate deal was found by Cheapflights users on 11/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/47:35 amPDX - MDW
1 stop14h 38mFrontier
Thu 12/1212:43 pmMDW - PDX
1 stop23h 04mFrontier
Deal found 11/20$213
This FlightHub deal was found by Cheapflights users on 11/19. 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.
Wed 12/1812:45 pmPDX - ORD
1 stop28h 49mFrontier
Thu 1/28:34 pmORD - PDX
1 stop23h 45mFrontier
Deal found 11/19$216
This Delta deal was found by Cheapflights users on 11/19. 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.
Tue 12/102:07 pmPDX - ORD
1 stop7h 52mDelta
Tue 12/176:45 pmORD - PDX
1 stop7h 43mDelta
Deal found 11/19$242
This Mytrip deal was found by Cheapflights users on 11/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/911:57 amBOI - ORD
3 stops35h 37mSpirit Airlines
Thu 12/129:53 pmORD - BOI
1 stop14h 05mSpirit Airlines
Deal found 11/18$245
This Delta deal was found by Cheapflights users on 11/20. 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.
Fri 12/611:10 amBOI - ORD
1 stop5h 52mDelta
Tue 12/177:10 pmORD - BOI
1 stop6h 33mDelta
Deal found 11/20$248
This United Airlines deal was found by Cheapflights users on 11/20. 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.
Fri 12/1311:59 pmPDX - ORD
Nonstop3h 49mUnited Airlines
Tue 12/1712:45 pmORD - PDX
1 stop7h 19mUnited Airlines
Deal found 11/20$252
This United Airlines deal was found by Cheapflights users on 11/19. 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.
Tue 12/315:20 pmBOI - ORD
1 stop5h 31mUnited Airlines
Tue 1/712:45 pmORD - BOI
1 stop6h 17mUnited Airlines
Deal found 11/19$268
This Delta deal was found by Cheapflights users on 11/19. 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.
Fri 12/131:13 pmMFR - ORD
1 stop6h 50mDelta
Mon 12/166:05 amORD - MFR
1 stop7h 14mDelta
Deal found 11/19$290
This Alaska Airlines deal was found by Cheapflights users on 11/19. 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 12/101:51 pmPDX - ORD
1 stop7h 56mAlaska Airlines
Fri 12/131:58 pmORD - PDX
Nonstop4h 31mAlaska Airlines
Deal found 11/19$291
This Delta deal was found by Cheapflights users on 11/19. 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.
Sat 12/1411:13 pmPDX - MDW
1 stop7h 45mDelta
Wed 12/189:38 amMDW - PDX
1 stop12h 52mDelta
Deal found 11/19$300

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 12/7

7:16 pm-5:30 am

1 stop8h 14m

Chicago O'Hare Intl

Tue 12/10

6:35 am-8:28 pm

3 stops15h 53m

$211

PortlandChicago

PDX - MDW

PDXMDW

Portland

Mon 2/10

12:03 pm-12:17 am

1 stop10h 14m

Chicago Midway

Sun 3/2

8:44 pm-8:40 am

1 stop13h 56m

$212

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 1/13

7:00 am-1:07 pm

Nonstop4h 07m

Chicago O'Hare Intl

Thu 1/16

10:47 pm-9:21 am

1 stop12h 34m

$213

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 12/18

12:45 pm-7:34 pm

1 stop28h 49m

Chicago O'Hare Intl

Thu 1/2

8:34 pm-6:19 pm

1 stop23h 45m

$216

PortlandChicago

PDX - ORD

PDXORD

Portland

Sun 2/9

7:00 am-1:07 pm

Nonstop4h 07m

Chicago O'Hare Intl

Tue 3/4

4:05 pm-6:44 pm

Nonstop4h 39m

$217

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 12/10

2:07 pm-11:59 pm

1 stop7h 52m

Chicago O'Hare Intl

Tue 12/17

6:45 pm-12:28 am

1 stop7h 43m

$242

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Mon 12/9

11:57 am-12:34 am

3 stops35h 37m

Chicago O'Hare Intl

Thu 12/12

9:53 pm-10:58 am

1 stop14h 05m

$245

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Fri 12/6

11:10 am-6:02 pm

1 stop5h 52m

Chicago O'Hare Intl

Tue 12/17

7:10 pm-12:43 am

1 stop6h 33m

$248

EugeneChicago

EUG - ORD

EUGORD

Eugene

Sun 1/5

6:59 pm-11:59 pm

1 stop27h 00m

Chicago O'Hare Intl

Sat 1/11

6:55 pm-9:08 pm

1 stop28h 13m

$263

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Tue 12/31

5:20 pm-11:51 pm

1 stop5h 31m

Chicago O'Hare Intl

Mon 1/6

4:00 pm-9:33 pm

1 stop6h 33m

$268

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 60 results
1
2
3
...
6

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, September is the cheapest month in which you can book a flight from Oregon to Chicago (average of $232). Flying from Oregon to Chicago in June is currently the most expensive (average of $308). 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 November 20, 2024.

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 November 20, 2024.

The most flights from USOR to CHI are scheduled on a Monday (19 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (6 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 November 20, 2024.
Read reviews from past customers who have flown Spirit Airlines, United Airlines and Alaska Airlines 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
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,461 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,171 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Allegiant Air
7.4
Good
850 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 Frontier, which is currently one of the cheapest options available, starting at $98. United Airlines flights start at $99 while deals on Southwest start at $99 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 Iberia (96%), Lufthansa (93%) and Hawaiian 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 $899, our data indicates the cheapest price to be $133. 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, September is the cheapest month in which you can book a flight from Oregon to Chicago (average of $232). Flying from Oregon to Chicago in June is currently the most expensive (average of $308). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Oregon to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Boston to O'Hare Intl flights
Newark to O'Hare Intl flights
Seattle to O'Hare Intl flights
Newark to Midway flights
Orlando to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Atlanta to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Denver to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Reagan-National to O'Hare Intl flights
Atlanta to Midway flights
Hobby to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Miami to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
LaGuardia to Midway flights
Los Angeles to Midway flights
Santa Ana to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Hobby to Midway flights
Baltimore to Midway flights
Burbank to O'Hare Intl flights
Ontario to O'Hare Intl flights
San Diego to O'Hare Intl flights
Tampa to O'Hare Intl flights
Minneapolis to Midway flights
Seattle to Midway flights
Dulles Intl to Midway flights
Orlando to Midway flights
Portland to O'Hare Intl flights
San Francisco to Midway flights
Austin to O'Hare Intl flights
Philadelphia to Midway flights
Miami to Midway flights
Newark to St. Louis flights
Love Field to O'Hare Intl flights
Denver to Midway flights
Nashville to O'Hare Intl flights
LaGuardia to St. Louis 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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$82Average$135FlexibilityNo cancel feeOn-time65%
FrontierCheapest$114Average$236FlexibilityNo cancel feeOn-time62%
DeltaCheapest$158Average$396FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$178Average$480FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$188Average$429FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$219Average$521FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$233Average$446FlexibilityNo cancel feeOn-time63%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines