Cheap flights from Portland (PDX) to Chicago (CHI) from $42

This is the cheapest one-way flight price, found on 10/1. Prices may vary by date and flight preferences.
PDX — CHI
Oct 8 — Oct 151

The best prices from Portland to Chicago are usually found in January or February, booked 60 days in advance, depart on a Saturday or Tuesday and return on a Sunday

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 2023: compare Portland to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.

Popular in

July

Cheapest in

January

Round-trip from

$207

One-way from

$76
High demand for flights, 31% potential price rise
Best time to find cheap flights, 32% potential price drop
From Portland to Chicago (CHI)
One-way flight from Portland to Chicago (CHI)

PDX - CHI

Price

$207 - $364

CHI

Temperature

23 - 73.4 °F

CHI

Rainfall

1.7 - 4.9 inches

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 30%.

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

Travelers have found it’s best to book a flight 61 days in advance to save up to 42% 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 61 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 $554, or $711 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 July. For low rates, January can be a great choice for travel to Chicago. Flights to Chicago from Portland in January are about $455 on average during January, but can be found for as low as $199.

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 40% on your trip compared to booking a flight in the morning.

Cheap Spirit Airlines flights from Portland to Chicago

Peruse some of the lowest-priced Spirit Airlines flights we've found from Portland to Chicago. Come back soon if you're not finding the exact deal you're looking for.
  • 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 35% cheaper than other airlines traveling the same route. Flights from Spirit Airlines typically cost $357.80 RT. The cheapest Spirit Airlines flight found for this route was $159. 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 14% more popular than any other airline flying that same route.

Cheap Alaska Airlines flights from Portland to Chicago

Have a look at some of the cheapest available Alaska Airlines flights departing from Portland and landing in Chicago. Make sure to examine the flight information before completing your reservation.
  • Alaska Airlines is one of the most popular airlines used for those traveling from Portland to Chicago. Flights on this route from Alaska Airlines typically cost $441.55 RT, a price that is 36% cheaper than the average Portland to Chicago flight. The cheapest flight found was $189 RT. 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, Alaska Airlines flights are 6% more popular than any other airline flying that same route.

Cheap Portland to Chicago flights in October & November 2023

The best prices found for PDX to CHI flights for October, November
These are some of the best deals we've found on flights to Chicago in 2023 at this time. Check back soon for alternative fares.

Portland to Chicago 2023 flight deals

Cheap flights to Chicago from Portland found for this year
These are some of the best deals we've found on flights to Chicago in 2023 at this time. Check back soon for alternative fares.

Non-stop flights to Chicago from Portland

Save time with Portland to Chicago direct flight deals
Consider booking one of these non-stop flights heading from Portland to Chicago. Search for alternative flights from Portland to Chicago by utilizing the search form above.

Portland to Chicago flights leaving soon

Late deals on return flights to Chicago from Portland, departing today and this week
Have a look at some of the last-minute flights available departing from Portland to Chicago. Users should be sure to double check the price, date, and time of their last-minute flight.

One-way flights to Chicago from Portland

The cheapest one-way flights from Portland to Chicago
Take a look at some of the best available options we've come across on one-way flights from Portland to Chicago. For those needing a return trip from Portland, there is a search form available above.

Find flights from Portland to Chicago within your budget

Use the slider to find flights from Portland to Chicago that fit your budget.

Fly from

Any airport

Fly to

Any airport

Budget

$88 - $238

Route

Depart

Return

Price

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Tue 11/14

1 stop15h 43m

Chicago Midway

Wed 11/29

1 stop17h 45m

PortlandChicago O'Hare Intl

PDX - ORD

PDXORD

Portland

Tue 10/24

1 stop10h 53m

Chicago O'Hare Intl

Tue 10/31

1 stop8h 51m

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Fri 11/3

1 stop15h 35m

Chicago Midway

Sat 11/11

1 stop21h 04m

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Tue 10/31

1 stop12h 19m

Chicago Midway

Tue 11/7

2 stops19h 56m

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Tue 11/14

1 stop15h 43m

Chicago Midway

Tue 11/28

2 stops17h 05m

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Tue 10/31

1 stop12h 19m

Chicago Midway

Mon 11/6

1 stop24h 39m

PortlandChicago O'Hare Intl

PDX - ORD

PDXORD

Portland

Tue 11/28

1 stop11h 45m

Chicago O'Hare Intl

Wed 11/29

1 stop8h 45m

PortlandChicago O'Hare Intl

PDX - ORD

PDXORD

Portland

Tue 10/24

Nonstop4h 00m

Chicago O'Hare Intl

Wed 11/1

Nonstop4h 34m

PortlandChicago O'Hare Intl

PDX - ORD

PDXORD

Portland

Wed 10/25

Nonstop3h 53m

Chicago O'Hare Intl

Tue 10/31

Nonstop4h 42m

Flights are sorted by cheapest first

Deals found on 10/2

Reviews of airlines servicing Chicago

See what other customers who have flown with Spirit Airlines, Alaska Airlines and Delta from Portland to Chicago have to say. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.1
Very good
1,394 reviews

Food

7.2

Boarding

8.3

Entertainment

7.2

Overall

8.1

Comfort

8.0

Crew

8.6

Reviews

1 / 10

I appreciated that we departed & arrived on time. I was very cold on the plane, despite wearing 2 jackets, & will bring a blanket next time. I appreciated the hot tea & cookie I was served. I also appreciated that our luggage was not lost or damaged.

Alaska Airlines
8.1
Very good
1,394 reviews
Alaska Airlines
8.1
Very good
1,394 reviews

Food

7.2

Boarding

8.3

Entertainment

7.2

Overall

8.1

Comfort

8.0

Crew

8.6

Reviews

1 / 10

I appreciated that we departed & arrived on time. I was very cold on the plane, despite wearing 2 jackets, & will bring a blanket next time. I appreciated the hot tea & cookie I was served. I also appreciated that our luggage was not lost or damaged.

Delta
7.9
Good
3,023 reviews
Alaska Airlines
8.1
Very good
1,394 reviews

Food

7.2

Boarding

8.3

Entertainment

7.2

Overall

8.1

Comfort

8.0

Crew

8.6

Reviews

1 / 10

I appreciated that we departed & arrived on time. I was very cold on the plane, despite wearing 2 jackets, & will bring a blanket next time. I appreciated the hot tea & cookie I was served. I also appreciated that our luggage was not lost or damaged.

Allegiant Air
7.5
Good
103 reviews
Alaska Airlines
8.1
Very good
1,394 reviews

Food

7.2

Boarding

8.3

Entertainment

7.2

Overall

8.1

Comfort

8.0

Crew

8.6

Reviews

1 / 10

I appreciated that we departed & arrived on time. I was very cold on the plane, despite wearing 2 jackets, & will bring a blanket next time. I appreciated the hot tea & cookie I was served. I also appreciated that our luggage was not lost or damaged.

Sun Country Air
7.4
Good
94 reviews
Alaska Airlines
8.1
Very good
1,394 reviews

Food

7.2

Boarding

8.3

Entertainment

7.2

Overall

8.1

Comfort

8.0

Crew

8.6

Reviews

1 / 10

I appreciated that we departed & arrived on time. I was very cold on the plane, despite wearing 2 jackets, & will bring a blanket next time. I appreciated the hot tea & cookie I was served. I also appreciated that our luggage was not lost or damaged.

United Airlines
7.4
Good
1,890 reviews
Alaska Airlines
8.1
Very good
1,394 reviews

Food

7.2

Boarding

8.3

Entertainment

7.2

Overall

8.1

Comfort

8.0

Crew

8.6

Reviews

1 / 10

I appreciated that we departed & arrived on time. I was very cold on the plane, despite wearing 2 jackets, & will bring a blanket next time. I appreciated the hot tea & cookie I was served. I also appreciated that our luggage was not lost or damaged.

Related info for your journey

Useful info, stats and facts about Portland to Chicago flights.

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 14 outbound flights to Chicago per day. 6 airlines have flights to Chicago from Portland on a regular basis.

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 $112.

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 $243.

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, Tuesday, Wednesday, Thursday, Friday, Saturday.

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

Travelers can expect 14 flights from Portland to Chicago on average per day.
Morning (6am - Noon) - 50% of flight departures
Afternoon (Noon - 6pm) - 50% of flight departures

How long is the flight from Portland to Chicago?

For as low as $88, Frontier can have you in Chicago from Portland in 11h 45m. 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 $88, 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 80% less than the average price by searching for these airlines.

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

$42 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 Alaska Airlines, with prices starting from $63 and $79, respectively.

What are the most popular routes from Portland to Chicago?

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

What are the most reliable airlines from Portland to Chicago?

Consider United Airlines (91%), Brussels Airlines (91%) or Aer Lingus (90%) when booking your flight. These represent the most reliable airlines when flying from Portland to Chicago.

What are the cheapest flights from Portland to Chicago?

While on average a flight from Portland to Chicago is generally $965, our data shows the cheapest flight currently is $98. When looking at the most popular route, (Portland - Chicago O'Hare Intl), you can expect to pay $116 for that flight.

What does PDX to ORD mean?

Portland Airport is PDX and Chicago O'Hare Intl Airport is ORD. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.

Top 6 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.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$120Average$241FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines flights
Alaska AirlinesCheapest$159Average$358FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights
FrontierCheapest$166Average$274FlexibilityNo cancel feeOn-time62%
Search Frontier flights
DeltaCheapest$178Average$496FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapest$189Average$442FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapest$199Average$397FlexibilityNo cancel feeOn-time71%
Search American Airlines flights

Hourly flight availability from Portland to Chicago

See what time of day planes typically take off from Portland to Chicago
3%of flight departuresEarly morningMidnight to 6 am
63%of flight departuresMorning6 am to noon
26%of flight departuresAfternoonNoon to 6 pm
8%of flight departuresEvening6 pm to midnight
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
Sunday14daily flights
Monday17daily flights
Tuesday16daily flights
Wednesday14daily flights
Thursday14daily flights
Friday15daily flights
Saturday12daily flights

Fly with Cheapflights

What makes Cheapflights the go-to destination for all your flight needs

How does Cheapflights help users find flights from Portland to Chicago?

Deals for Portland to Chicago flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Portland to Chicago?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Portland to Chicago for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Portland to Chicago with no change fees?

Yes! Cheapflights helps users easily find flights from Portland to Chicago with no change fees.

Can Cheapflights notify me if prices for flights from Portland to Chicago become cheaper?

Of course! You can now track prices for flights from Portland to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and make a flight search when you’re ready to set up your price alert.

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