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 2022: 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 60 days in advance to save up to 58% 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 60 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 $446, or $593 for flights within the next 24 hours.

When is the cheapest time to fly from Oregon to Chicago (OR - CHI)?

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.

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

Our data shows that October tends to be the cheapest month to fly to Chicago from Oregon. Users have commonly found prices around $368 for the month, but tickets can be as low as $158. Due to multiple factors, prepare for potentially higher prices in June.

Cheap flights from Oregon to Chicago in August, September 2022

The best prices found for Oregon to CHI flights for August, September
23 Sep - 28 Sep
$161pp
PDX
Portland
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
PDX
Portland
10 Sep - 14 Sep
$162pp
PDX
Portland
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
PDX
Portland
9 Sep - 12 Sep
$164pp
PDX
Portland
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
PDX
Portland

Oregon to Chicago 2022 flight deals

Cheap flights to Chicago from Oregon found for this year
7 Oct - 18 Oct
$161pp
PDX
Portland
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
PDX
Portland
10 Sep - 14 Sep
$162pp
PDX
Portland
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
PDX
Portland
9 Sep - 12 Sep
$164pp
PDX
Portland
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
PDX
Portland

Cheap Delta flights from Oregon to Chicago

1 Oct - 5 Oct
$304pp
RDM
Bend/Redmond
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
RDM
Bend/Redmond
30 Sep - 4 Oct
$324pp
RDM
Bend/Redmond
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
RDM
Bend/Redmond
4 Oct - 8 Oct
$334pp
RDM
Bend/Redmond
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
RDM
Bend/Redmond

Cheap Alaska Airlines flights from Oregon to Chicago

5 Sep - 9 Sep
$398pp
RDM
Bend/Redmond
Alaska Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
   
2 STOPS
RDM
Bend/Redmond
12 Sep - 15 Sep
$424pp
RDM
Bend/Redmond
Alaska Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
 
1 STOP
RDM
Bend/Redmond
16 Aug - 28 Aug
$935pp
MFR
Medford
Alaska Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
   
2 STOPS
MFR
Medford

Non-stop flights to Chicago from Oregon

Save time with Oregon to Chicago direct flight deals
5 Nov - 12 Nov
$277pp
PDX
Portland
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
Non-Stop
PDX
Portland
5 Nov - 12 Nov
$278pp
PDX
Portland
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
PDX
Portland
3 Sep - 4 Oct
$284pp
PDX
Portland
United 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
15 Aug - 22 Oct
$264pp
PDX
Portland
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
PDX
Portland
15 Aug - 22 Oct
$269pp
PDX
Portland
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
   
2 STOPS
PDX
Portland
15 Aug - 29 Aug
$272pp
MFR
Medford
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
MFR
Medford

One-way flights to Chicago from Oregon

The cheapest one-way flights from Oregon to Chicago
7:59 pm - 1:55 am
American Airlines
Nonstop
3h 56m
PDX - ORD
American Airlines
5:17 pm - 1:56 pm
Frontier
2 Stops
18h 39m
PDX - MDW
Frontier
$135
CheapOair
5:50 pm - 8:18 am
Multiple Airlines
1 Stop
12h 28m
PDX - RFD
Multiple Airlines
$136
Kiwi.com

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

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 $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 $161, but on average you can expect to pay $190.

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 $320.

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 can be found on the following days: Sunday, Tuesday, Wednesday, Thursday, Friday, Saturday.

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

Per day, 13 flights depart from Oregon to Chicago on average.
Morning (6am - Noon) - 54% of flight departures
Evening (6pm - Midnight) - 46% of flight departures

How long is the flight from Oregon to Chicago?

Departing from Oregon to Chicago will take you 11h 17m. Airlines will cover a distance of 1744 mi.

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 $86. Spirit Airlines flights start at $114 while deals on American Airlines start at $129 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 Eugene - Chicago O'Hare Intl.

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

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

What are the most reliable airlines from Oregon to Chicago?

The top 3 most reliable airlines when flying from Oregon to Chicago are Qatar Airways (96%), Aer Lingus (93%) and United Airlines (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 $553, our data indicates the cheapest price to be $173. The most popular route (Portland - Chicago O'Hare Intl), is priced around $232.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

Do I need a COVID test to fly to Chicago from Oregon?

Information is based on travel restrictions for travel to Chicago within the United States

Most visitors from Oregon need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Oregon are not required to present a negative COVID-19 PCR test or antigen result upon entering Chicago.

Quarantine requirements
Visitors from Oregon are not required to quarantine after entering Chicago.

Do I need a test to fly back to Oregon from Chicago?

Returning to Oregon from Chicago

COVID-19 testing requirements
Visitors from Chicago are not required to present a negative COVID-19 PCR test or antigen result upon entering Oregon.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Oregon.

Hide COVID Travel Restrictions for Chicago, IL

Departure points for flights from Oregon to Chicago

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

Top 7 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
Juneyao Airlines
$16 $22 No cancel fee 66%

We couldn't confirm the COVID-19 safety measures taken by Juneyao Airlines. Please check directly on their website for additional information.

Frontier
$61 $227 No cancel fee 62%
Spirit Airlines
$99 $368 No cancel fee 65%
Alaska Airlines
$118 $381 No cancel fee 75%
Delta
$138 $434 No cancel fee N/A
American Airlines
$138 $428 No cancel fee 71%
United Airlines
$159 $549 No cancel fee 69%