Cheap flights from Portland to Chicago (PWM - 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 August or July, booked 60 days in advance, depart on a Saturday or Thursday and return on a Wednesday

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

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

$163

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 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 52% on the flight price compared to flying in the morning, which is usually more expensive.

Cheap flights from Portland to Chicago in May, June 2021

The best prices found for PWM to CHI flights for May, June
26 May - 28 May
$209pp
PWM
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
PWM
Portland
19 May - 23 May
$222pp
PWM
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PWM
Portland
20 May - 23 May
$223pp
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

Cheap flights to Chicago from Portland found for this year
26 May - 28 May
$209pp
PWM
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
PWM
Portland
28 Oct - 1 Nov
$219pp
PWM
Portland
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
PWM
Portland
19 May - 23 May
$222pp
PWM
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PWM
Portland

Non-stop flights to Chicago from Portland

Save time with Portland to Chicago direct flight deals
28 Oct - 1 Nov
$219pp
PWM
Portland
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
PWM
Portland
24 Jun - 28 Jun
$231pp
PWM
Portland
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
PWM
Portland
15 Oct - 20 Oct
$239pp
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

Late deals on round-trip flights to Chicago from Portland, departing today and this week
26 May - 28 May
$209pp
PWM
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
PWM
Portland
26 May - 28 May
$238pp
PWM
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
PWM
Portland
22 May - 23 May
$247pp
PWM
Portland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PWM
Portland

One-way flights to Chicago from Portland

The cheapest one-way flights from Portland to Chicago
1:32 pm - 12:27 pm
Frontier
1 Stop
23h 55m
PWM - ORD
Frontier
$163
Kiwi.com
8:20 am - 12:04 pm
American Airlines
1 Stop
4h 44m
PWM - ORD
American Airlines
2:24 pm - 8:04 am
United Airlines
2 Stops
18h 40m
PWM - ORD
United Airlines
$169
United

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.

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.

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 (PWM) is just 2.9 mi from the center of the city. Portland is the only Portland airport and it handles 6 outbound flights to Chicago per day. 5 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 Multiple Airlines for just $209, but on average you can expect to pay $239.

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 $308.

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?

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

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 40m. United Airlines provides one of the quickest options available for as low as $259. 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 $219. Other airlines that can offer you cheap pricing are American Airlines, from $228, and Delta, from $237. United Airlines is 38% 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 $90. United Airlines flights start at $119 while deals on American Airlines start at $137 one-way.

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Portland to Chicago.
Flight duration
2h 38m
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 3 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
American Airlines
$144 $348 No cancel fee 71%
Delta
$105 $351 No cancel fee N/A
United Airlines
$199 $405 No cancel fee 69%

Hourly flight availability from Portland to Chicago

See what time of day planes typically take off from Portland towards Chicago.
Afternoon Noon to 6 PM 53% of PWM to CHI departures
Early morning Midnight to 6 AM 47% of PWM to CHI departures
Morning 6 AM to noon 0% of PWM to CHI departures
Evening 6 PM to midnight 0% of PWM 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
7 daily flights
Monday
7 daily flights
Tuesday
6 daily flights
Wednesday
5 daily flights
Thursday
7 daily flights
Friday
7 daily flights
Saturday
5 daily flights
Home North America USA Illinois Chicago Cheap flights from Portland to Chicago