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

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

All the information you need to plan the best CHI to PDX flight in 2021: compare Chicago to Oregon flight prices with the expected peak season, weather and rainfall in Oregon.
How far in advance should I book a flight from Chicago to Oregon?

To save on the cost of your flight from Chicago to Oregon, book at least 17 days before your planned departure. Booking around this time can save you about 17% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $104 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $129.

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

The best pricing can be found in the month of April. Prices to Oregon from Chicago average $112. You can even find prices in April for less than $112, as users have found deals to Oregon from as low as $41. The month of December appears to be one of the more expensive times to travel to Oregon from Chicago. Flying in the targeted month can save you up to 39%.

Cheap flights from Chicago to Oregon in May, June 2021

The best prices found for CHI to Oregon flights for May, June
10 May - 17 May
$139pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland
PDX
Portland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
19 May - 21 May
$150pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland
PDX
Portland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
18 May - 22 May
$151pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
PDX
Portland
PDX
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Chicago to Oregon 2021 flight deals

Cheap flights to Oregon from Chicago found for this year
10 May - 17 May
$139pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland
PDX
Portland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
19 May - 21 May
$150pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland
PDX
Portland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
18 May - 22 May
$151pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
PDX
Portland
PDX
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Non-stop flights to Oregon from Chicago

Save time with Chicago to Oregon direct flight deals
5 Jun - 9 Jun
$197pp
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
PDX
Portland
PDX
Portland
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
5 Jun - 7 Jun
$217pp
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
PDX
Portland
PDX
Portland
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
15 Jun - 19 Jun
$235pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
PDX
Portland
PDX
Portland
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Oregon

Late deals on round-trip flights to Oregon from Chicago, departing today and this week
10 May - 17 May
$139pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland
PDX
Portland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
10 May - 17 May
$180pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
PDX
Portland
PDX
Portland
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
11 May - 14 May
$190pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
PDX
Portland
PDX
Portland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl

One-way flights to Oregon from Chicago

The cheapest one-way flights from Chicago to Oregon
3:55 pm - 6:16 pm
Alaska Airlines
Nonstop
4h 21m
ORD - PDX
Alaska Airlines
4:30 am - 10:27 am
Frontier
1 Stop
7h 57m
ORD - PDX
Frontier
$122
Kiwi.com
2:30 am - 7:06 am
Spirit Airlines
2 Stops
30h 36m
ORD - PDX
Spirit Airlines
$124
Gotogate

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Chicago</span> to <span class="emphasized">Oregon</span> flights.

Flight FAQs

From Chicago to Oregon

Are flight prices decreasing from Chicago to Oregon 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 Chicago and Oregon 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 Chicago to Oregon 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 Chicago to Oregon 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 Chicago to Oregon have flexible cancellations due to COVID-19?

Some of our airline partners flying from Chicago to Oregon have new flexible policies in place due to COVID-19. United Airlines, Alaska Airlines, and American Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like United Airlines with this kind of flexibility.

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

Yes, there are multiple flights from Chicago to Oregon for under $200. The cheapest flight booked recently is on Frontier for just $139, but on average you can expect to pay $184.

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

Cheapflights has at least 20 direct flights from Chicago to Oregon under $200. A good price for a nonstop flight from Chicago to Oregon is less than $254.

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

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

What days are nonstop flights available from Chicago to Oregon?

You can find nonstop flights on the following days: Sunday, Monday, Friday, Saturday.

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

Major Airline, American Airlines and Alaska Airlines are the most popular airlines when flying from Chicago to Oregon.

What are the most popular routes from Chicago to Oregon?

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

What are the cheapest Flights from Chicago to Oregon?

On average you can expect to pay $533 for a flight from Chicago to Oregon. The cheapest flight overall is $121 while the most popular route, (Chicago O'Hare Intl - Portland) is currently priced at $190.

What are the most reliable airlines from Chicago to Oregon?

Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Oregon on time: Qatar Airways(100%), Air Canada(95%), United Airlines(95%.)

How long is the flight from Chicago to Oregon?

There are many flights that can get you from Chicago to Oregon in 4h 19m. Fly via United Airlines, Alaska Airlines, or Delta to get the fastest option. This flight may include one or multiple stops.

What are the cheapest airlines flying from Chicago to Oregon round-trip?

Cheapflights users have booked flights from Chicago to Oregon round-trip from $139. Other airlines that can offer you cheap pricing are United Airlines, from $197, and Spirit Airlines, from $205.

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

For one-way options, check prices for Frontier. According to our data, you can fly for as low as $68. Users have also found prices from $106 and $108 on Frontier and Spirit Airlines, respectively.

Destination points for flights from Chicago to Oregon

Select to see more specific information for flights from Chicago to all places in Oregon.

Destination information for Oregon

Things to know before you go - useful duration and weather info for your trip from Chicago to Oregon.
Flight duration
4h 06m

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Airports servicing

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

Top 7 airlines flying from Chicago to Oregon

The chart below displays the airlines Cheapflights users traveling from Chicago to Oregon 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
$96 $206 No cancel fee 62%
Sun Country Air
$131 $239 No cancel fee 83%
Spirit Airlines
$116 $244 No cancel fee 65%
American Airlines
$140 $312 No cancel fee 71%
Alaska Airlines
$140 $330 No cancel fee 75%
Delta
$134 $385 No cancel fee N/A
United Airlines
$140 $426 No cancel fee 69%
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