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

Home North America USA Illinois Chicago Cheap flights from Portland to Chicago

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
23 - 73.4 °F
CHI
Precipitation
1.7 - 4.9 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 (CHI)

One-way from

$84

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

Thursday is generally a great day to depart. Flying on this day could help you save up to 18%.

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

Travelers have found it’s best to book a flight 17 days in advance to save up to 13% 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 17 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 $275, or $324 for flights within the next 24 hours.

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, August can be a great choice for travel to Chicago. Flights to Chicago from Portland in August are about $274 on average during August, but can be found for as low as $118.

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 18% on your trip compared to booking a flight at noon.

Cheap flights from Portland to Chicago in October, November 2021

The best prices found for PDX to CHI flights for October, November
3 Nov - 6 Nov
$117pp
PDX
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland
2 Nov - 3 Nov
$119pp
PDX
Portland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
PDX
Portland
2 Nov - 6 Nov
$121pp
PDX
Portland
Multiple Airlines
 
1 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
8 Dec - 11 Dec
$116pp
PDX
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland
3 Nov - 6 Nov
$117pp
PDX
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland
2 Nov - 3 Nov
$119pp
PDX
Portland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
PDX
Portland

Non-stop flights to Chicago from Portland

Save time with Portland to Chicago direct flight deals
9 Feb - 15 Feb
$176pp
PDX
Portland
Major Airline
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Major Airline
Non-Stop
PDX
Portland
20 Nov - 4 Dec
$177pp
PDX
Portland
Alaska Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
Non-Stop
PDX
Portland
20 Jan - 22 Jan
$183pp
PDX
Portland
Major Airline
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Major Airline
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
3 Nov - 6 Nov
$117pp
PDX
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland
2 Nov - 3 Nov
$119pp
PDX
Portland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
PDX
Portland
2 Nov - 6 Nov
$121pp
PDX
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland

One-way flights to Chicago from Portland

The cheapest one-way flights from Portland to Chicago
7:59 pm - 5:13 am
Frontier
1 Stop
7h 14m
PDX - ORD
Frontier
$84
Travelocity
2:10 pm - 4:13 pm
Multiple Airlines
1 Stop
24h 03m
PDX - RFD
Multiple Airlines
$88
FareScan
9:24 am - 8:03 pm
Spirit Airlines
3 Stops
32h 39m
PDX - ORD
Spirit Airlines
$97
FareScan

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 24 outbound flights to Chicago per day. 9 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 Multiple Airlines for just $116, but on average you can expect to pay $138.

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 $217.

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.

What days are nonstop flights available from Portland to Chicago?

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

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

Travelers can expect 38 flights from Portland to Chicago on average per day.
Early Morning (Midnight to 6am) - 16% of flight departures
Morning (6am - Noon) - 82% of flight departures
Evening (6pm - Midnight) - 3% of flight departures

How long is the flight from Portland to Chicago?

For as low as $119, Spirit Airlines can have you in Chicago from Portland in 8h 35m. 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?

Spirit Airlines, at $119, was found to be the cheapest airline from Portland to Chicago. An alternate airline flying to your destination would be Frontier. 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?

$54 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and Alaska Airlines, with prices starting from $65 and $89, respectively.

What are the most reliable airlines from Portland to Chicago?

Consider Aer Lingus (95%), LOT (90%) or Iberia (89%) when booking your flight. These represent the most reliable 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.

What are the cheapest flights from Portland to Chicago?

While on average a flight from Portland to Chicago is generally $628, our data shows the cheapest flight currently is $122. When looking at the most popular route, (Portland - Chicago O'Hare Intl), you can expect to pay $116 for that flight.

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

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

Related searches

Flights to Chicago from Portland (PDX)
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Other flights from Portland

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Other flights to Chicago

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Rent a Car

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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 must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to 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 must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to 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.
Portland to Bloomington Bloomington-Normal from $453 pp
Medford to Bloomington Bloomington-Normal from $718 pp

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Portland to Chicago.
Average temperature for October in Chicago
64.4 °F
Avg rainfall for October in Chicago
2.6 ″

Airports servicing Portland

Portland (PDX)

Airports servicing Chicago

O'Hare Intl (ORD)
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%
Delta 		$139 $401 No cancel fee N/A
American Airlines 		$140 $331 No cancel fee 71%
Alaska Airlines 		$140 $318 No cancel fee 75%
United Airlines 		$140 $386 No cancel fee 69%
Sun Country Air 		$141 $272 No cancel fee 83%
Southwest 		$374 $506 No cancel fee 63%

Popular flight searches

Check out other popular destinations found by fellow travelers in 2021.

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 75% of PDX to CHI departures
Early morning Midnight to 6 AM 15% of PDX to CHI departures
Evening 6 PM to midnight 10% of PDX to CHI departures
Afternoon Noon to 6 PM 0% 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
11 daily flights
Monday
31 daily flights
Tuesday
29 daily flights
Wednesday
33 daily flights
Thursday
26 daily flights
Friday
28 daily flights
Saturday
14 daily flights
Home North America USA Illinois Chicago Cheap flights from Portland to Chicago