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Cheap flights from Portland to Chicago (PWM - CHI)

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The best prices from Portland to Chicago are usually found in August or July, booked 60 days in advance, depart on a Saturday or Thursday and return on a Tuesday

How to find the cheapest flight from
Portland (PWM) to Chicago (CHI)

PWM - CHI
Price
$191 - $409
CHI
Temperature
33.8 - 84.2 °F
CHI
Rainfall
0.7 - 4.3 inches

Popular in

April

High demand for flights, 12% potential price rise

Cheapest in

August

Best time to find cheap flights, 47% potential price drop

Round-trip from

$191

From Portland to Chicago

One-way from

$92

One-way flight from Portland to Chicago

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Portland to Chicago?

Sunday flights are found to be more expensive to fly from Portland to Chicago. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago.

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

April is one of the best times of the year to fly to Chicago from Portland. Prices for April average $135 per person but you can even find prices for as low as $33. The most expensive prices can be found in the month of December. Opting for a April flight can save you 49% on your journey compared to booking in April

When is the cheapest time to fly from Portland to Chicago (PWM - CHI)?

It’s typically best to fly out from Portland to Chicago in the evening. Doing so could potentially save you 25% on the flight price compared to flying in the morning, which is usually more expensive.

Cheap flights from Portland to Chicago in January, February 2021

24 Feb - 3 Mar
$142pp
PWM
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
PWM
Portland
24 Feb - 3 Mar
$149pp
PWM
Portland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PWM
Portland
24 Feb - 3 Mar
$151pp
PWM
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
PWM
Portland

Portland to Chicago 2021 flight deals

24 Feb - 3 Mar
$142pp
PWM
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
PWM
Portland
24 Feb - 3 Mar
$149pp
PWM
Portland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PWM
Portland
24 Feb - 3 Mar
$151pp
PWM
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
PWM
Portland

Non-stop flights to Chicago from Portland

1 Apr - 6 Apr
$219pp
PWM
Portland
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
PWM
Portland
14 Mar - 17 Mar
$239pp
PWM
Portland
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
PWM
Portland
9 Apr - 11 Apr
$259pp
PWM
Portland
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
PWM
Portland

Last minute flights from Portland to Chicago

3 Feb - 7 Feb
$336pp
PWM
Portland
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
PWM
Portland
3 Feb - 7 Feb
$339pp
PWM
Portland
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
PWM
Portland
3 Feb - 7 Feb
$343pp
PWM
Portland
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
PWM
Portland

One-way flights to Chicago from Portland

8:41 am - 5:55 pm
Frontier
1 Stop
10h 14m
PWM - ORD
Frontier
$92
Kiwi.com
2:00 am - 7:45 am
American Airlines
1 Stop
6h 45m
PWM - ORD
American Airlines
12:50 am - 9:21 am
Delta
2 Stops
9h 31m
PWM - ORD
Delta
$143
Delta

Related info for your journey

Flight FAQs

From Portland to Chicago

Are flight prices decreasing from Portland 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 Portland 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 Portland to Chicago to control the spread of COVID-19?

New policies can now be found on Delta to help keep travelers safe while flying. New policies for travelers booking flights from Portland to Chicago include masks being provided and required on board, daily cleaning and sanitization, use of HEPA filters, pre-flight testing for antibodies and symptoms, and socially distanced seating (for a limited time). Keep in mind that policies will vary by airline.

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

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

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

Yes, there are multiple flights from Portland to Chicago for under $200. The cheapest flight booked recently is on Multiple Airlines for just $142, but on average you can expect to pay $197.

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

Cheapflights has at least 8 direct flights from Portland to Chicago under $300. A good price for a nonstop flight from Portland to Chicago is less than $316.

Are there last-minute flights available from Portland to Chicago for under $400?

There are currently 7+ open flights from Portland to Chicago within the next 7 days for less than $400.

What days are nonstop flights available from Portland to Chicago?

Nonstop flights can be found on the following days: Tuesday.

Is Portland weather warmer or cooler than Chicago?

Temperatures around the 84 °F's can be experienced in July. The weather in Chicago is hotter than in Portland. Plan for potential changes in flight availability as peak weather approaches in this location.

How long is the flight from Portland to Chicago?

A quick flight from Portland to Chicago can take about 2h 52m. American Airlines provides one of the quickest options available for as low as $266. This flight may include one or multiple stops.

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

Cheapflights users have booked flights from Portland to Chicago round-trip from $149. Other airlines that can offer you cheap pricing are Delta, from $233, and American Airlines, from $234. Frontier is 58% cheaper than the average price of flights available within the next 90 days to this destination.

What are the cheapest airlines to fly from Portland 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 $50. American Airlines flights start at $117 while deals on Delta start at $123 one-way.

Destination information for Chicago

Flight duration
2h 45m
Average temperature for January in Chicago
33.8 °F
Avg rainfall for January in Chicago
0.7 ″

Airports servicing Portland

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 3 airlines flying from Portland to Chicago

Airline Cheapest Average Flexibility On-time COVID-19 safety
American Airlines
$144 $348 No cancel fee 71%
Delta
$105 $351 No cancel fee N/A
United Airlines
$199 $405 No cancel fee 69%
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