Cheap flights from Portland to Chicago (PDX - CHI)

Know your dates, get live prices in seconds:

From
To
Depart
Return
Any month
Compare vs. Cheapflights |
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime

We work with more than 300 partners to bring you better travel deals

The best prices from Portland to Chicago are usually found in October or January, booked 60 days in advance, depart on a Saturday or Wednesday 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 2022: compare Portland to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
PDX - CHI
Price
$246 - $623
CHI
Temperature
23 - 73.4 °F
CHI
Rainfall
1.7 - 4.9 inches

Popular in

June

High demand for flights, 41% potential price rise

Cheapest in

October

Best time to find cheap flights, 33% potential price drop

Round-trip from

$246

From Portland to Chicago (CHI)

One-way from

$129

One-way flight from Portland to Chicago (CHI)

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
How far in advance should I book a flight from Portland 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 Portland 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 Portland to Chicago (PDX - CHI)?

A simple way to save on the total cost of your ticket is to fly from Portland to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 39% on your trip compared to booking a flight at noon.

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

Due to multiple factors, expect to potentially pay more when booking in June. For low rates, October can be a great choice for travel to Chicago. Flights to Chicago from Portland in October are about $368 on average during October, but can be found for as low as $158.

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

Friday is generally a great day to depart. Flying on this day could help you save up to 34%.

Cheap flights from Portland to Chicago in August, September 2022

The best prices found for PDX to CHI flights for August, September
23 Sep - 27 Sep
$161pp
PDX
Portland
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
PDX
Portland
29 Sep - 4 Oct
$162pp
PDX
Portland
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
PDX
Portland
9 Sep - 16 Sep
$164pp
PDX
Portland
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
PDX
Portland

Portland to Chicago 2022 flight deals

Cheap flights to Chicago from Portland found for this year
23 Sep - 27 Sep
$161pp
PDX
Portland
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
PDX
Portland
29 Sep - 4 Oct
$162pp
PDX
Portland
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
PDX
Portland
7 Oct - 12 Oct
$164pp
PDX
Portland
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
PDX
Portland

Cheap Spirit Airlines flights from Portland to Chicago

4 Nov - 7 Nov
$217pp
PDX
Portland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
PDX
Portland
3 Nov - 6 Nov
$231pp
PDX
Portland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
PDX
Portland
3 Nov - 6 Nov
$236pp
PDX
Portland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
PDX
Portland

If you’re traveling from Portland to Chicago, one of the more common airlines traveling that route is Spirit Airlines. Portland to Chicago flights are typically 56% cheaper than other airlines traveling the same route. Flights from Spirit Airlines typically cost $389.61 RT. The cheapest Spirit Airlines flight found for this route was $118. When traveling from Portland to Chicago on Spirit Airlines, the most popular airport to depart from is Portland Airport and the most popular airport to arrive at is Chicago O'Hare Intl Airport. When flying from Portland to Chicago, Spirit Airlines flights are 23% more popular than any other airline flying that same route.

Cheap United Airlines flights from Portland to Chicago

21 Aug - 2 Sep
$391pp
PDX
Portland
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
PDX
Portland

One of the most popular airlines traveling from Portland to Chicago is Frontier. Flights from Frontier traveling this route typically cost $536.20 RT. This price is typically 30% cheaper than other airlines that offer Portland to Chicago flights. When booking this route, the cheapest RT price found was $159. Portland Airport is the most common Portland airport to take off from when flying to Chicago. Chicago O'Hare Intl Airport is the most popular arrival airport in Chicago. When flying from Portland to Chicago, Frontier flights are 19% more popular than any other airline flying that same route.

Non-stop flights to Chicago from Portland

Save time with Portland to Chicago direct flight deals
9 Nov - 12 Nov
$258pp
PDX
Portland
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American 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 Portland to Chicago

Late deals on round-trip flights to Chicago from Portland, departing today and this week
19 Aug - 30 Aug
$253pp
PDX
Portland
Frontier
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
PDX
Portland
21 Aug - 31 Aug
$271pp
PDX
Portland
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
PDX
Portland
19 Aug - 30 Aug
$292pp
PDX
Portland
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
PDX
Portland

One-way flights to Chicago from Portland

The cheapest one-way flights from Portland to Chicago
6:59 pm - 12:55 am
American Airlines
Nonstop
3h 56m
PDX - ORD
American Airlines
5:57 pm - 1:25 am
Frontier
1 Stop
29h 28m
PDX - ORD
Frontier
$133
Kiwi.com
4:35 pm - 10:55 am
Multiple Airlines
3 Stops
40h 20m
PDX - MDW
Multiple Airlines
$134
Kiwi.com

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

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 26 outbound flights to Chicago per day. 10 airlines have flights to Chicago from Portland on a regular basis.

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 $200 on Cheapflights?

Yes, there are multiple flights from Portland to Chicago for under $200. The cheapest flight booked recently is on Frontier for just $161, but on average you can expect to pay $194.

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 $313.

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: Sunday, Tuesday, Thursday, Friday, Saturday.

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

Travelers can expect 10 flights from Portland to Chicago on average per day.
Morning (6am - Noon) - 40% of flight departures
Evening (6pm - Midnight) - 60% of flight departures

How long is the flight from Portland to Chicago?

For as low as $161, Frontier can have you in Chicago from Portland in 11h 32m. Airlines will cover a distance of 1744 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

Frontier, at $161, was found to be the cheapest airline from Portland to Chicago. An alternate airline flying to your destination would be Spirit Airlines. You may be able to fly from Portland to Chicago for 56% less than the average price by searching for these airlines.

What are the cheapest airlines to fly from Portland to Chicago one-way?

$86 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and American Airlines, with prices starting from $108 and $129, respectively.

What are the cheapest flights from Portland to Chicago?

While on average a flight from Portland to Chicago is generally $553, our data shows the cheapest flight currently is $173. When looking at the most popular route, (Portland - Chicago O'Hare Intl), you can expect to pay $237 for that flight.

What are the most reliable airlines from Portland to Chicago?

Consider Qatar Airways (96%), Aer Lingus (93%) or United Airlines (93%) when booking your flight. These represent the most reliable airlines when flying from Portland to Chicago.

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

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

What are the most popular routes from Portland to Chicago?

When deciding which route to take from Portland to Chicago consider Portland - Chicago O'Hare Intl, Portland - Chicago Midway or Portland - Chicago Greater Rockford as they are the most popular.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

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

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

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

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

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

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

Returning to Portland 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 Portland.

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

Hide COVID Travel Restrictions for Chicago, IL

Alternative routes for Portland to Chicago

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

Top 7 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
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 $390 No cancel fee 75%
Delta
$138 $437 No cancel fee N/A
American Airlines
$158 $403 No cancel fee 71%
United Airlines
$159 $536 No cancel fee 69%

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 46% of PDX to CHI departures
Early morning Midnight to 6 AM 36% of PDX to CHI departures
Afternoon Noon to 6 PM 15% of PDX to CHI departures
Evening 6 PM to midnight 3% 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
27 daily flights
Monday
28 daily flights
Tuesday
22 daily flights
Wednesday
28 daily flights
Thursday
25 daily flights
Friday
27 daily flights
Saturday
28 daily flights