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$54+ 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
nov. 9 — nov. 161
1 adult
sáb. 11/9
sáb. 11/16
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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 noviembre 4, 2024.

This FareScan deal was found by Cheapflights users on 11/4. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/82:52 pmPDX - ORD
1 stop12h 38mSpirit Airlines
mié. 12/119:10 pmORD - PDX
1 stop28h 38mSpirit Airlines
Deal found 11/4$197
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
vie. 11/157:33 pmPDX - ORD
1 stop7h 12mMultiple Airlines
dom. 11/179:27 pmORD - PDX
1 stop12h 40mMultiple Airlines
Deal found 11/3$203
This KAYAK deal was found by Cheapflights users on 11/3. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/612:03 pmPDX - ORD
1 stop10h 32mFrontier
mié. 12/186:00 amORD - PDX
1 stop11h 44mFrontier
Deal found 11/3$204
This Frontier deal was found by Cheapflights users on 11/3. 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.
jue. 11/1410:56 amPDX - MDW
1 stop12h 02mFrontier
dom. 11/1710:59 pmMDW - PDX
1 stop11h 58mFrontier
Deal found 11/3$208
This Alaska Airlines deal was found by Cheapflights users on 11/3. 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. 12/77:00 amPDX - ORD
Nonstop4h 02mAlaska Airlines
mié. 12/111:58 pmORD - PDX
Nonstop4h 31mAlaska Airlines
Deal found 11/3$217
This Mytrip deal was found by Cheapflights users on 11/4. 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.
mar. 11/1911:51 amBOI - ORD
1 stop15h 54mSpirit Airlines
jue. 11/211:09 pmORD - BOI
2 stops22h 47mSpirit Airlines
Deal found 11/4$229
This Delta deal was found by Cheapflights users on 11/3. 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. 12/43:34 pmPDX - ORD
1 stop6h 24mDelta
mar. 12/106:45 pmORD - PDX
1 stop7h 43mDelta
Deal found 11/3$236
This Sun Country Air deal was found by Cheapflights users on 11/2. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/126:37 pmPDX - ORD
1 stop14h 18mSun Country Air
lun. 12/1611:33 amORD - PDX
1 stop7h 31mSun Country Air
Deal found 11/2$265
This Delta deal was found by Cheapflights users on 11/4. 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.
mar. 11/195:35 amBOI - ORD
1 stop6h 45mDelta
mié. 11/207:00 pmORD - BOI
1 stop6h 33mDelta
Deal found 11/4$268
This Delta deal was found by Cheapflights users on 11/3. 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.
sáb. 11/165:35 amBOI - MDW
2 stops11h 57mDelta
lun. 11/189:30 amMDW - BOI
1 stop5h 55mDelta
Deal found 11/3$273
This Alaska Airlines deal was found by Cheapflights users on 11/3. 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. 12/75:00 amEUG - ORD
1 stop16h 47mAlaska Airlines
mar. 12/107:00 amORD - EUG
1 stop15h 54mAlaska Airlines
Deal found 11/3$274
This Delta deal was found by Cheapflights users on 11/3. 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.
mar. 12/35:25 pmEUG - ORD
1 stop17h 55mDelta
mié. 12/116:05 amORD - EUG
1 stop6h 42mDelta
Deal found 11/3$275

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 2,455,398 searches. Data last updated noviembre 4, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

mar. 12/3

11:51 am-4:35 am

1 stop15h 44m

$92

PortlandChicago

PDX - MDW

PDXMDW

Portland

jue. 11/14

6:46 pm-6:16 pm

1 stop21h 30m

$93

PortlandChicago

PDX - ORD

PDXORD

Portland

mié. 1/22

7:00 am-1:07 pm

Nonstop4h 07m

$109

PortlandChicago

PDX - MDW

PDXMDW

Portland

mié. 1/8

9:00 am-2:55 pm

Nonstop3h 55m

$109

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

mié. 4/30

5:40 am-1:05 pm

1 stop6h 25m

$114

PortlandChicago

PDX - ORD

PDXORD

Portland

sáb. 12/28

11:55 pm-5:56 am

Nonstop4h 01m

$114

PortlandChicago

PDX - ORD

PDXORD

Portland

jue. 1/2

5:57 pm-10:57 am

1 stop15h 00m

$130

PortlandChicago

PDX - ORD

PDXORD

Portland

lun. 12/30

12:59 am-10:35 am

1 stop7h 36m

$178

PortlandChicago

PDX - ORD

PDXORD

Portland

sáb. 11/9

11:21 am-8:32 am

1 stop19h 11m

$94

PortlandChicago

PDX - ORD

PDXORD

Portland

vie. 11/22

9:40 pm-11:52 am

1 stop12h 12m

$98

Flights are sorted by cheapest first

Deals found on 11/3

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, 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 noviembre 4, 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 noviembre 4, 2024.

The most flights from USOR to CHI are scheduled on a Monday (19 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 noviembre 4, 2024.
Read reviews from past customers who have flown Alaska Airlines, Delta and American 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
5,089 reviews

Boarding

8.3

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

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

Southwest
8.1
Very good
5,089 reviews
Southwest
8.1
Very good
5,089 reviews

Boarding

8.3

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

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

Alaska Airlines
8.0
Very good
9,423 reviews
Southwest
8.1
Very good
5,089 reviews

Boarding

8.3

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

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

Delta
8.0
Very good
8,829 reviews
Southwest
8.1
Very good
5,089 reviews

Boarding

8.3

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

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

United Airlines
7.4
Good
9,226 reviews
Southwest
8.1
Very good
5,089 reviews

Boarding

8.3

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

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

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
5,089 reviews

Boarding

8.3

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

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.

  • Can I find flights from Oregon to Chicago for under $200 on Cheapflights?

    Yes, there are multiple flights from Oregon to Chicago for under $200. The cheapest flight booked recently is on Frontier for just $112, but on average you can expect to pay $231.

  • Are there nonstop flights from Oregon to Chicago for under $200 on Cheapflights?

    Cheapflights has at least 4 direct flights from Oregon to Chicago under $200. A good price for a nonstop flight from Oregon to Chicago is less than $249.

  • Are there last-minute flights available from Oregon to Chicago for under $200?

    There are currently 20+ open flights from Oregon to Chicago within the next 7 days for less than $200.

  • What days are nonstop flights available from Oregon to Chicago?

    Nonstop flights can be found on the following days: Monday, Tuesday, Wednesday, Friday, Saturday.

  • How many flights depart from Oregon to Chicago on average per day?

    Per day, 6 flights depart from Oregon to Chicago on average.
    Morning (6am - Noon) - 67% of flight departures
    Evening (6pm - Midnight) - 33% of flight departures

  • How long is the flight from Oregon to Chicago?

    Departing from Oregon to Chicago will take you 3h 59m. Airlines will cover a distance of 1744 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 $54. Spirit Airlines flights start at $60 while deals on Alaska Airlines start at $90 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 Spirit Airlines (100%), Iberia (99%) and Qatar Airways (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 $875, our data indicates the cheapest price to be $103. The most popular route (Portland - Chicago O'Hare Intl), is priced around $121.

  • What does PDX to ORD mean?

    These are just IATA (International Air Transport Association) codes. They are used in aviation to identify and differentiate airports. That’s why a Portland Airport to Chicago O'Hare Intl Airport flight would often be abbreviated as a PDX to ORD flight. This flight route has multiple associated airports, so we think it might be helpful to learn the name and codes of them as well. They are Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from Oregon to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Oregon to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Oregon to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Oregon to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Oregon to Chicago that allow pets onboard?

    Many airlines flying from Oregon to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Oregon to Chicago?

    Yes, you can often find last-minute deals on Oregon to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Oregon to Chicago flight deals updated?

    The Oregon to Chicago flight deals you see on this page were last updated on 11/4.

  • 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

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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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LaGuardia to O'Hare Intl flights
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Dallas/Fort Worth to O'Hare Intl flights
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Boston to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
John F Kennedy Intl to Midway flights
Newark to Midway flights
Atlanta to O'Hare Intl flights
Los Angeles to Midway flights
Reagan-National to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Denver to O'Hare Intl flights
Orlando to O'Hare Intl flights
Hobby to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Hobby to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Miami to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Burbank to O'Hare Intl flights
Atlanta to Midway flights
Ontario to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Minneapolis to Midway flights
Tampa to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Austin to O'Hare Intl flights
Baltimore to Midway flights
San Francisco to Midway flights
San Diego to O'Hare Intl flights
Portland to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
LaGuardia to Midway flights
Hartford to O'Hare Intl flights
Newark to St. Louis flights
Dulles Intl to Midway flights
San Jose to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Columbus to O'Hare Intl flights
Love Field to O'Hare Intl flights
George Bush Intcntl to Midway flights
LaGuardia to St. Louis flights
Kansas City 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 2,455,398 searches. Data last updated noviembre 4, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$82Average$136FlexibilityNo cancel feeOn-time65%
FrontierCheapest$114Average$228FlexibilityNo cancel feeOn-time62%
DeltaCheapest$158Average$402FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$178Average$490FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$188Average$421FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$219Average$519FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$233Average$404FlexibilityNo cancel feeOn-time63%
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