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

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

All the information you need to plan the best null to CHI flight in 2021: compare Oregon to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
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 May, June 2021

The best prices found for Oregon to CHI flights for May, June
21 Jun - 25 Jun
$157pp
EUG
Eugene
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
EUG
Eugene
28 Jun - 3 Jul
$216pp
EUG
Eugene
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
EUG
Eugene
29 Jun - 4 Jul
$225pp
EUG
Eugene
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
EUG
Eugene

Oregon to Chicago 2021 flight deals

Cheap flights to Chicago from Oregon found for this year
5 Dec - 14 Dec
$157pp
EUG
Eugene
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
EUG
Eugene
5 Dec - 17 Dec
$186pp
EUG
Eugene
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
EUG
Eugene
28 Jun - 3 Jul
$216pp
EUG
Eugene
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
EUG
Eugene

Non-stop flights to Chicago from Oregon

Save time with Oregon to Chicago direct flight deals
14 Sep - 18 Sep
$237pp
PDX
Portland
Alaska Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
Non-Stop
PDX
Portland
16 Sep - 20 Sep
$250pp
PDX
Portland
Major Airline
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Major Airline
Non-Stop
PDX
Portland
17 Sep - 21 Sep
$251pp
PDX
Portland
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United 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
22 May - 25 May
$249pp
PDX
Portland
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland
22 May - 23 May
$251pp
PDX
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
Non-Stop
PDX
Portland
24 May - 26 May
$253pp
PDX
Portland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
PDX
Portland

One-way flights to Chicago from Oregon

The cheapest one-way flights from Oregon to Chicago
3:31 pm - 2:30 am
Spirit Airlines
1 Stop
8h 59m
PDX - ORD
Spirit Airlines
$122
JustFly
4:14 pm - 7:43 pm
Frontier
1 Stop
25h 29m
PDX - ORD
Frontier
$126
Kiwi.com
8:35 pm - 9:18 am
United Airlines
1 Stop
10h 43m
PDX - ORD
United Airlines
$128
United

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Oregon</span> to <span class="emphasized">Chicago</span> 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 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 $300 on Cheapflights?

Yes, there are multiple flights from Oregon to Chicago for under $300. The cheapest flight booked recently is on Alaska Airlines for just $237, but on average you can expect to pay $254.

Are there nonstop flights from Oregon to Chicago for under $300 on Cheapflights?

Cheapflights has at least 20 direct flights from Oregon to Chicago under $300. A good price for a nonstop flight from Oregon to Chicago is less than $270.

Are there last-minute flights available from Oregon to Chicago for under $300?

There are currently 20+ open flights from Oregon to Chicago within the next 7 days for less than $300.

What days are nonstop flights available from Oregon to Chicago?

Nonstop flights are available for this route on the following days: Wednesday, Friday, Saturday.

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 $628 for a flight from Oregon to Chicago. The cheapest flight overall is $123 while the most popular route, (Portland - Chicago O'Hare Intl) is currently priced at $249.

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 LOT (100%), SWISS (100%) or Lufthansa (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 45m. All flights are typically nonstop.

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

Cheapflights users have booked flights from Oregon to Chicago round-trip from $237. Other airlines that can offer you cheap pricing are American Airlines, from $246, and Major Airline, from $250.

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 $108 on Spirit Airlines. Other airlines that offer cheap prices include Alaska Airlines from $108 and Frontier from $126 one-way.

Departure points for flights from Oregon to Chicago

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

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Oregon to Chicago.
Flight duration
4h 08m
Average temperature for May in Chicago
71.6 °F
Avg rainfall for May in Chicago
4.3 ″

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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