Are direct flights from Portland to Chicago always the best option?

Direct flights offer convenience by reducing travel time and avoiding layovers, which can be appealing. However, connecting flights are often more affordable than direct routes. Travelers should weigh the cost savings against the added travel time and potential for delays.

Can flexible travel dates help on Portland to Chicago flights?

Yes, being flexible with your travel dates can significantly impact the price of your flight. Flying on weekdays, during off-peak seasons, or avoiding major holidays often results in lower fares. Even shifting your travel by a day or two can sometimes yield better deals.

What extra costs should I check before booking Portland to Chicago flights?

Before booking, always check for potential extra costs such as baggage fees, seat selection charges, and in-flight services. Some airlines may also charge for printing boarding passes at the airport. Factor these into your total travel budget to avoid surprises.

Flights From Portland

To Chicago

Portland to Chicago Flights — [2026]

Browse current best options from Portland. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Portland

RatePunk searches hundreds of travel sites at once for deals on flights to Chicago

Prices updated today

485 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Nov 2, 2026.)

Today’s best flight deals from Portland to Chicago

Explore current cheapest deals departing from Portland to Chicago

2027-01-21 – 2027-02-03
PDX - Chicago
66% AI deal score
$236
$241
Round trip
2027-01-24 – 2027-02-03
PDX - Chicago
66% AI deal score
$241
$245
Round trip
2027-01-21 – 2027-01-27
PDX - Chicago
67% AI deal score
$256
$250
Round trip
2027-01-24 – 2027-01-27
PDX - Chicago
68% AI deal score
$264
$254
Round trip
2027-01-07 – 2027-02-03
PDX - Chicago
66% AI deal score
$225
$255
Round trip
2027-01-26 – 2027-02-03
PDX - Chicago
50% AI deal score
$199
$261
Round trip
2027-01-12 – 2027-02-03
PDX - Chicago
49% AI deal score
$176
$261
Round trip
2027-01-07 – 2027-01-27
PDX - Chicago
66% AI deal score
$226
$264
Round trip
2027-01-21 – 2027-02-16
PDX - Chicago
50% AI deal score
$227
$270
Round trip
2027-01-21 – 2027-02-09
PDX - Chicago
50% AI deal score
$228
$270
Round trip

Portland to Chicago: Overview

Insights for flights from Portland to Chicago

Flights from Portland to Chicago cover a distance of 2,811 kilometers, placing this route in the medium-haul category. This means you can expect a journey that balances significant distance with reasonable travel times. New deals show up several times a week, so keeping an eye on price fluctuations can be beneficial for finding cheap flights from Portland to Chicago.

Fares for this route typically range from $424–$951, with a median price of $630. Right now, current fares are above the typical level, indicating that prices are higher than the historical median for this route. Only 1% of recent fares were classified as a good price, suggesting that finding a low fare may require some flexibility or advance planning.

When is the cheapest time to fly from Portland to Chicago? The data indicates that the most affordable months to travel are December, with a median fare of $345, followed by February at $352, and April at $389. Planning your trip during these months could result in significant savings compared to other times of the year.

For flights from Portland to Chicago, most itineraries connect at least once, with only 12.7% of recent fares being non-stop. When connections are involved, the typical number of stopovers is 2. This means you should generally expect a journey with at least one layover.

How long is the flight from Portland to Chicago? A typical journey, including connections, takes approximately 9h 50m. For the limited number of direct flights from Portland to Chicago, the non-stop flight time is around 4h 6m. Given that most itineraries involve connections, the overall travel time tends to be considerably longer than the direct flight duration.

How much is a round trip from Portland to Chicago

Regular price: $215 - $328

Prices for flights from Portland to Chicago are currently within the regular range.

The regular price range for flights from Portland to Chicago is typically between $215 and $328. The current lowest deal is $227 with Frontier Airlines for travel from Dec 3-Dec 6.

now $227

Low $215

High $328

The cheapest time to fly from Portland to Chicago

The cheapest month to fly from Portland to Chicago is January, with a median price of $245. The most expensive month is July, with a median price of $689. Prices are generally lower from January to December.

January

Cheapest

Flights from $245

July

Most Expensive

Flights from $689

Jan

Feb

Apr

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Portland to Chicago

United Airlines

Last-minute flights going from Portland to Chicago

Tue, Oct 27

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

Frontier Airlines

$458

$452

One-way

Fri, Oct 30

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

Frontier Airlines

$446

$455

One-way

Tue, Nov 10

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

Frontier Airlines

$324

$309

One-way

Thu, Nov 19

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

Frontier Airlines

$307

$296

One-way

Fri, Nov 20

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

Frontier Airlines

$306

$285

One-way

Sat, Nov 21

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

Frontier Airlines

$306

$266

One-way

Biggest price drops on these dates for flights from Portland to Chicago

6 nights

Nov 17 - Nov 23

$289 → $249

14%

2 nights

Nov 21 - Nov 23

$306 → $266

13%

3 nights

Dec 3 - Dec 6

$266 → $227

15%

3 nights

Nov 20 - Nov 23

$307 → $285

Popular Airports to fly from Portland to Chicago

Portland - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares from Portland to Chicago are above the typical level, with a median price of $630.

📅 Best time to fly

Fly in December for the best prices

Historically, December offers the lowest median price at $345, followed by February at $352.

⏱️ Flight duration

Direct flights take 4h 6m

The median flight duration for a direct flight is 4h 6m, while connecting flights average 9h 50m.

✈️ Airlines & availability

Connecting flights are dominant

Only 12.7% of recent flights are direct, with connecting flights typically having 2 stopovers.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines is one of the carriers providing direct flights on the Portland to Chicago route.

🎯 Booking tip

Deals appear regularly

Deals for flights from Portland to Chicago appear regularly, typically within a 30-day window.

Portland main airports to depart from

Portland International (PDX)

Cheapest

Portland International is a convenient option for flights from Portland to Chicago.

📍 ~10 km from city center (reachable by car or train)

💸 Flights from ~$265

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O Hare International Airport is a good option for flights from Portland to Chicago.

📍 ~25 km from Chicago city center (reachable by car)

💸 Flights from ~$196

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and is easily accessible from Chicago.

📍 ~135 km from Chicago (reachable by car or train)

💸 Flights from ~$311

Business & First Class Flight Deals to Chicago

Discover luxury on the budget with premium cabin class on flights from Portland to Chicago.

Elite

Best Elite deals to Chicago

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From PDX

Elite

Mar 06

Chicago, United States

91% AI deal score

$2,146

$974

Save $1,172

Alaska Airlines, Inc.

Business Class

From PDX

Elite

Dec 16

Chicago, United States

90% AI deal score

$1,756

$900

Save $856

Alaska Airlines, Inc.

Business Class

From PDX

Elite

Dec 24

Chicago, United States

90% AI deal score

$1,825

$917

Save $908

Alaska Airlines, Inc.

Business Class

From PDX

Elite

Dec 24

Chicago, United States

90% AI deal score

$1,773

$917

Save $856

Alaska Airlines, Inc.

Business Class

From PDX

Elite

Dec 13

Chicago, United States

90% AI deal score

$1,756

$920

Save $836

Alaska Airlines, Inc.

Business Class

From PDX

Elite

Dec 16

Chicago, United States

90% AI deal score

$1,828

$920

Save $908

Alaska Airlines, Inc.

Business Class

From PDX

Elite

Dec 07

Chicago, United States

90% AI deal score

$1,760

$929

Save $831

Alaska Airlines, Inc.

Business Class

From PDX

Elite

Dec 07

Chicago, United States

90% AI deal score

$1,847

$929

Save $918

Alaska Airlines, Inc.

Business Class

From PDX

Elite

Dec 10

Chicago, United States

90% AI deal score

$1,829

$929

Save $900

Alaska Airlines, Inc.

Business Class

From PDX

Elite

Dec 13

Chicago, United States

90% AI deal score

$1,821

$940

Save $881

Alaska Airlines, Inc.

Business Class

From PDX

Elite

Dec 10

Chicago, United States

90% AI deal score

$1,832

$952

Save $880

Alaska Airlines, Inc.

Business Class

From PDX

Elite

Dec 16

Chicago, United States

90% AI deal score

$2,004

$981

Save $1,023

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Chicago

To find more affordable flights, consider being flexible with your travel dates and times. Comparing prices across different airlines and booking sites can often reveal better deals. Setting up price alerts may also notify you of fare drops.

Booking flights in advance, typically several weeks or months before your desired departure, may often result in lower prices. However, prices can fluctuate, so monitoring fares over time can be beneficial. Last-minute deals are less common but can sometimes appear.

Yes, comparing nearby airports at both your origin and destination can sometimes lead to more economical flight options. While it may require additional travel time to and from these airports, the potential savings on airfare can be significant. Always factor in the total cost and convenience.

Related routes

More routes from Portland

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Flights to Chicago from other cities

Flights from Louisville to Chicago Flights from Philadelphia to Chicago Flights from Phoenix to Chicago Flights from Pittsburgh to Chicago Flights from Prague to Chicago Flights from Raleigh to Chicago Flights from Reno to Chicago Flights from Reykjavik to Chicago Flights from Sacramento to Chicago Flights from San Antonio to Chicago Flights from San Diego to Chicago Flights from Seattle to Chicago

Portland to Chicago: Overview

Insights for flights from Portland to Chicago

How much is a round trip from Portland to Chicago

Regular price: $215 - $328

Prices for flights from Portland to Chicago are currently within the regular range.

The regular price range for flights from Portland to Chicago is typically between $215 and $328. The current lowest deal is $227 with Frontier Airlines for travel from Dec 3-Dec 6.

now $227

Low $215

High $328

The cheapest time to fly from Portland to Chicago

January

Cheapest

Flights from $245

July

Most Expensive

Flights from $689

Jan

Feb

Apr

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Portland to Chicago

United Airlines

Last-minute flights going from Portland to Chicago

Tue, Oct 27

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

Frontier Airlines

$458

$452

One-way

Fri, Oct 30

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

Frontier Airlines

$446

$455

One-way

Tue, Nov 10

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

Frontier Airlines

$324

$309

One-way

Thu, Nov 19

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

Frontier Airlines

$307

$296

One-way

Fri, Nov 20

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

Frontier Airlines

$306

$285

One-way

Sat, Nov 21

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

Frontier Airlines

$306

$266

One-way

Biggest price drops on these dates for flights from Portland to Chicago

6 nights

Nov 17 - Nov 23

$289 → $249

14%

2 nights

Nov 21 - Nov 23

$306 → $266

13%

3 nights

Dec 3 - Dec 6

$266 → $227

15%

3 nights

Nov 20 - Nov 23

$307 → $285

Popular Airports to fly from Portland to Chicago

Portland - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares from Portland to Chicago are above the typical level, with a median price of $630.

📅 Best time to fly

Fly in December for the best prices

Historically, December offers the lowest median price at $345, followed by February at $352.

⏱️ Flight duration

Direct flights take 4h 6m

The median flight duration for a direct flight is 4h 6m, while connecting flights average 9h 50m.

✈️ Airlines & availability

Connecting flights are dominant

Only 12.7% of recent flights are direct, with connecting flights typically having 2 stopovers.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines is one of the carriers providing direct flights on the Portland to Chicago route.

🎯 Booking tip

Deals appear regularly

Deals for flights from Portland to Chicago appear regularly, typically within a 30-day window.

Portland main airports to depart from

Portland International (PDX)

Cheapest

Portland International is a convenient option for flights from Portland to Chicago.

📍 ~10 km from city center (reachable by car or train)

💸 Flights from ~$265

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O Hare International Airport is a good option for flights from Portland to Chicago.

📍 ~25 km from Chicago city center (reachable by car)

💸 Flights from ~$196

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and is easily accessible from Chicago.

Chicago, United States

90% AI deal score

$2,004

$981

Save $1,023

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Chicago

Portland to Chicago Flights — [2026]

Today’s best flight deals from Portland to Chicago

Portland to Chicago: Overview

Insights for flights from Portland to Chicago

How much is a round trip from Portland to Chicago

The cheapest time to fly from Portland to Chicago

Direct flights from Portland to Chicago

Last-minute flights going from Portland to Chicago

Biggest price drops on these dates for flights from Portland to Chicago

Popular Airports to fly from Portland to Chicago

Portland - Chicago route insights

Recent fares are above the typical level

Fly in December for the best prices

Direct flights take 4h 6m

Connecting flights are dominant

United Airlines offers direct flights

Deals appear regularly

Portland main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Mar 06

Dec 16

Dec 24

Dec 24

Dec 13

Dec 16

Dec 07

Dec 07

Dec 10

Dec 13

Dec 10

Dec 16

Frequently Asked Questions About Flights to Chicago

How can I find cheap flights from Portland to Chicago?

When should I book flights from Portland to Chicago?

Should I compare nearby airports for flights from Portland to Chicago?

Are direct flights from Portland to Chicago always the best option?

Can flexible travel dates help on Portland to Chicago flights?

What extra costs should I check before booking Portland to Chicago flights?

Related routes

More routes from Portland

Flights to Chicago from other cities

Portland to Chicago: Overview

Insights for flights from Portland to Chicago

How much is a round trip from Portland to Chicago

The cheapest time to fly from Portland to Chicago

Direct flights from Portland to Chicago

Last-minute flights going from Portland to Chicago

Biggest price drops on these dates for flights from Portland to Chicago

Popular Airports to fly from Portland to Chicago

Portland - Chicago route insights

Recent fares are above the typical level

Fly in December for the best prices

Direct flights take 4h 6m

Connecting flights are dominant

United Airlines offers direct flights

Deals appear regularly

Portland main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Mar 06

Dec 16

Dec 24

Dec 24

Dec 13

Dec 16

Dec 07

Dec 07

Dec 10

Dec 13

Dec 10

Dec 16

Frequently Asked Questions About Flights to Chicago

How can I find cheap flights from Portland to Chicago?

When should I book flights from Portland to Chicago?

Should I compare nearby airports for flights from Portland to Chicago?