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Cheap flights from Oregon (OR) to Chicago (CHI)

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How to find the cheapest flight from
Oregon to Chicago (CHI)

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

Travelers have found it’s best to book a flight 20 days in advance to save up to 10% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 20 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Oregon to Chicago 1-2 weeks in advance for as low as $137, or $157 for flights within the next 24 hours.

What is the cheapest month to fly from Oregon to Chicago?

April can be a great time to fly to Chicago from Oregon with a flight ticket averaging about $135. Cheapflights users have found deals in the month of April for as cheap as $33. The most expensive prices can be found in the month of December.

Cheap flights from Oregon to Chicago in January, February 2021

The best prices found for Oregon to CHI flights for January, February
18 Feb - 22 Feb
$93pp
PDX
Portland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland
1 Feb - 6 Feb
$112pp
PDX
Portland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland
22 Feb - 1 Mar
$114pp
PDX
Portland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland

Oregon to Chicago 2021 flight deals

Cheap flights to Chicago from Oregon found for this year
18 Feb - 22 Feb
$93pp
PDX
Portland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland
1 Feb - 6 Feb
$112pp
PDX
Portland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland
22 Feb - 1 Mar
$114pp
PDX
Portland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland

Non-stop flights to Chicago from Oregon

Save time with Oregon to Chicago direct flight deals
12 May - 18 May
$197pp
PDX
Portland
Alaska Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
Non-Stop
PDX
Portland
12 May - 17 May
$217pp
PDX
Portland
Alaska Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
Non-Stop
PDX
Portland
18 Feb - 22 Feb
$237pp
PDX
Portland
Alaska Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
Non-Stop
PDX
Portland

Last minute flights from Oregon to Chicago

Late deals on round-trip flights to Chicago from Oregon, departing today and this week
1 Feb - 6 Feb
$112pp
PDX
Portland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland
1 Feb - 6 Feb
$140pp
PDX
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
PDX
Portland
4 Feb - 7 Feb
$154pp
PDX
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
   
2 STOPS
PDX
Portland

One-way flights to Chicago from Oregon

The cheapest one-way flights from Oregon to Chicago
4:59 am - 1:00 am
Frontier
2 Stops
42h 01m
PDX - ORD
Frontier
$76
Kiwi.com
4:47 am - 3:27 pm
Multiple Airlines
1 Stop
8h 40m
MFR - ORD
Multiple Airlines
$91
Kiwi.com
1:46 pm - 7:55 am
Spirit Airlines
1 Stop
16h 09m
PDX - ORD
Spirit Airlines
$95
Gotogate

Related info for your journey

Useful info, stats and facts about Oregon to Chicago flights.

Flight FAQs

From Oregon to Chicago

Are flight prices decreasing from Oregon to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Oregon and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

What safety measures are being taken by airlines flying from Oregon to Chicago to control the spread of COVID-19?

New policies can now be found on Alaska Airlines and Delta to help keep travelers safe while flying. Some of the new policies that have been implemented to accommodate travelers flying from Oregon to Chicago are improved sanitation, HEPA filters, mask requirements, social distance seating (for a limited time), and pre-flight testing for antibodies and symptoms. Policies will vary by airline.

Which airlines flying from Oregon to Chicago have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Oregon to Chicago that may be offering flexible cancellation policies are United Airlines, Alaska Airlines, and American Airlines. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

Can I find flights from Oregon to Chicago for under $100 on Cheapflights?

Yes, there are multiple flights from Oregon to Chicago for under $100. The cheapest flight booked recently is on Frontier for just $93, but on average you can expect to pay $129.

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

Cheapflights has at least 20 direct flights from Oregon to Chicago under $200. A good price for a nonstop flight from Oregon to Chicago is less than $347.

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 are available for this route on the following days: Monday.

What are the most popular airlines that fly from Oregon to Chicago?

When booking a flight from Oregon to Chicago, you may want to consider flying on Major Airline, American Airlines or Alaska Airlines as they are the most popular for this route.

What are the most popular routes from Oregon to Chicago?

While some choose either Portland - Chicago Midway or Eugene - Chicago O'Hare Intl, Portland - Chicago O'Hare Intl is the most popular route from Oregon to Chicago.

What are the cheapest Flights from Oregon to Chicago?

On average you can expect to pay $634 for a flight from Oregon to Chicago. The cheapest flight overall is $129 while the most popular route, (Portland - Chicago O'Hare Intl) is currently priced at $116.

What are the most reliable airlines from Oregon to Chicago?

No one likes to see their flight delayed. When booking a flight from Oregon to Chicago consider choosing Malaysia Airlines (100%), Gulf Air (100%) or British Airways (100%) as they are the most reliable in getting you off to your destination on time.

How long is the flight from Oregon to Chicago?

Departing from Oregon to Chicago will take you 3h 35m. This flight may include one or multiple stops.

What is the cheapest airline to fly from Oregon to Chicago round-trip?

Cheapflights users have booked flights from Oregon to Chicago round-trip from $93.

What are the cheapest airlines to fly from Oregon to Chicago one-way?

One-way options have recently been found by users for as low as $44 on Frontier. Another option is Spirit Airlines, who have fights from $65.

Destination information for Chicago

Things to know before you go. Useful info for your trip from Oregon to Chicago
Average temperature for January in Chicago
33.8 °F
Avg rainfall for January in Chicago
0.7 ″

Airports servicing

Klamath Falls (LMT)
Medford (MFR)
North Bend (OTH)
Pendleton (PDT)
Portland (PDX)

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 8 airlines flying from Oregon to Chicago

The chart below displays the airlines Cheapflights users traveling from Oregon to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.

Airline Cheapest Average Flexibility On-time COVID-19 safety
Frontier
$106 $233 No cancel fee 62%
Spirit Airlines
$116 $254 No cancel fee 65%
Sun Country Air
$141 $272 No cancel fee 83%
Alaska Airlines
$129 $321 No cancel fee 75%
American Airlines
$140 $354 No cancel fee 71%
United Airlines
$140 $421 No cancel fee 69%
Delta
$131 $444 No cancel fee N/A
Southwest
$374 $506 No cancel fee 63%
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