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)

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

$128

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 18% on the cost of your flight, compared to a flight at noon.

Cheap flights from Portland to Chicago in May, June 2021

The best prices found for PDX to CHI flights for May, June
7 Jun - 8 Jun
$246pp
PDX
Portland
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
PDX
Portland
19 May - 25 May
$248pp
PDX
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland
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

Portland to Chicago 2021 flight deals

Cheap flights to Chicago from Portland found for this year
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
14 Sep - 18 Sep
$241pp
PDX
Portland
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
PDX
Portland
7 Jun - 8 Jun
$246pp
PDX
Portland
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
PDX
Portland

Non-stop flights to Chicago from Portland

Save time with Portland 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 Portland to Chicago

Late deals on round-trip flights to Chicago from Portland, 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 Portland

The cheapest one-way flights from Portland to Chicago
8:35 pm - 9:18 am
United Airlines
1 Stop
10h 43m
PDX - ORD
United Airlines
$128
United
4:14 pm - 1:09 pm
Frontier
2 Stops
42h 55m
PDX - ORD
Frontier
$130
Kiwi.com
7:50 pm - 1:45 am
Major Airline
Nonstop
3h 55m
PDX - ORD
Major Airline
$135
StudentUniverse

Related info for your journey

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

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 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.

What airport do you fly from for flights from Portland to Chicago?

For a flight from Portland to Chicago, you will be flying from Portland. Portland (PDX) is just 6.0 mi from the center of the city. Portland is the only Portland airport and it handles 12 outbound flights to Chicago per day. 9 airlines have flights to Chicago from Portland on a regular basis.

Can I find flights from Portland to Chicago for under $300 on Cheapflights?

Yes, there are multiple flights from Portland 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 Portland to Chicago for under $300 on Cheapflights?

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

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

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

What days are nonstop flights available from Portland to Chicago?

Days when nonstop flights are available for this flight are: Wednesday, Friday, Saturday.

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

Travelers can expect 2 flights from Portland to Chicago on average per day.
Morning (6am - Noon) - 100% of flight departures

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 $250, Major Airline can have you in Chicago from Portland in 3h 45m. The distance from Portland to Chicago is about 1744 mi. Generally, flights for this route are nonstop.

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

Alaska Airlines, at $237, was found to be the cheapest airline from Portland to Chicago.Alternate airlines to your destination round-trip include American Airlines and Major Airline. Users have found that Alaska Airlines is 13% 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 Spirit Airlines, which is currently one of the cheapest options available, starting at $108. Alaska Airlines flights start at $119 while deals on Frontier start at $126 one-way.

Alternative routes for Portland to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Portland 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 Portland

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 8 airlines flying from Portland to Chicago

The chart below displays the airlines Cheapflights users traveling from Portland 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
$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

See what time of day planes typically take off from Portland towards Chicago.
Morning 6 AM to noon 80% of PDX to CHI departures
Evening 6 PM to midnight 9% of PDX to CHI departures
Early morning Midnight to 6 AM 6% of PDX to CHI departures
Afternoon Noon to 6 PM 5% of PDX to CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Portland to Chicago
See how many times per day planes take to the skies headed from Portland to Chicago.
Sunday
16 daily flights
Monday
17 daily flights
Tuesday
4 daily flights
Wednesday
5 daily flights
Thursday
11 daily flights
Friday
20 daily flights
Saturday
15 daily flights
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