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Cheap flights from Portland to Chicago (PDX - CHI)

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The best prices from Portland to Chicago are usually found in August or April, booked 19 days in advance, depart on a Friday or Tuesday and return on a Wednesday

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

PDX - CHI
Price
$236 - $349
CHI
Temperature
33.8 - 84.2 °F
CHI
Rainfall
0.7 - 4.3 inches

Popular in

December

High demand for flights, 21% potential price rise

Cheapest in

August

Best time to find cheap flights, 14% potential price drop

Round-trip from

$236

From Portland to Chicago

One-way from

$76

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?

Saturday flights are generally found to be more expensive for flights 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?

Find a great deal and save up to 10% by booking at least 20 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Portland to Chicago within the next two weeks, with the cheapest ticket starting at $137.

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

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, April can be a great choice for travel to Chicago. Flights to Chicago from Portland in April are about $135 on average during April, but can be found for as low as $33.

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

It’s optimal to fly from Portland to Chicago in the afternoon. By choosing this option you can save up to 15% on the cost of your flight, compared to a flight in the morning.

Cheap flights from Portland to Chicago in January, February 2021

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
4 Feb - 5 Mar
$110pp
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

Portland to Chicago 2021 flight deals

11 Mar - 31 Mar
$88pp
PDX
Portland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland
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
12 Mar - 15 Mar
$98pp
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 Portland

14 Apr - 5 May
$197pp
PDX
Portland
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
PDX
Portland
11 May - 23 May
$217pp
PDX
Portland
Alaska Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
Non-Stop
PDX
Portland
9 Feb - 16 Feb
$227pp
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 Portland to Chicago

4 Feb - 5 Mar
$110pp
PDX
Portland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland
5 Feb - 6 Mar
$116pp
PDX
Portland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland
5 Feb - 9 Feb
$124pp
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 Portland

4:59 am - 1:00 am
Frontier
2 Stops
42h 01m
PDX - ORD
Frontier
$76
Kiwi.com
1:12 pm - 9:51 am
Multiple Airlines
2 Stops
18h 39m
PDX - ORD
Multiple Airlines
$85
Kiwi.com
5:40 am - 3:51 am
Spirit Airlines
2 Stops
20h 11m
PDX - ORD
Spirit Airlines
$87
FlightHub

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 Alaska Airlines and 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, 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 Portland to Chicago for under $100 on Cheapflights?

Yes, there are multiple flights from Portland to Chicago for under $100. The cheapest flight booked recently is on Frontier for just $88, but on average you can expect to pay $119.

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

Cheapflights has at least 20 direct flights from Portland to Chicago under $200. A good price for a nonstop flight from Portland to Chicago is less than $304.

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

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

Is Portland weather warmer or cooler than Chicago?

You can imagine temperatures to be in the 84 °F range in July. The weather in Chicago is generally hotter than Portland's. As flight availability is subject to become more limited as peak season approaches it is ideal to book in a timely manner.

How long is the flight from Portland to Chicago?

For as low as $331, Delta can have you in Chicago from Portland in 5h 55m. Both multi-stop and nonstop flights can be found to your destination and back.

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

Frontier, at $88, was found to be the cheapest airline from Portland to Chicago.. Users have found that Frontier is 67% cheaper than the other options available 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 $41. Frontier is not the only option available. At the moment, Spirit Airlines is another option, for $54.

Alternative routes for Portland to Chicago

Destination information for Chicago

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 8 airlines flying from Portland to Chicago

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
$140 $318 No cancel fee 75%
American Airlines
$140 $331 No cancel fee 71%
United Airlines
$140 $386 No cancel fee 69%
Delta
$139 $401 No cancel fee N/A
Southwest
$374 $506 No cancel fee 63%

Hourly flight availability from Portland to Chicago

Morning 6 AM to noon 68% of PDX to CHI departures
Early morning Midnight to 6 AM 27% of PDX to CHI departures
Afternoon Noon to 6 PM 5% of PDX to CHI departures
Evening 6 PM to midnight 0% of PDX to CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Portland to Chicago
Sunday
8 daily flights
Monday
9 daily flights
Tuesday
5 daily flights
Wednesday
3 daily flights
Thursday
9 daily flights
Friday
8 daily flights
Saturday
5 daily flights
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