What percentage of Portland to Chicago flights are direct?

In the trailing 90 days, approximately 34.2% of flights from Portland to Chicago have been direct. For journeys that include connecting flights, travelers typically experience a median of 2 stopovers. This indicates that a significant portion of routes involve at least one stop.

Are there frequently good prices on flights from Portland to Chicago?

Historically, good prices on flights from Portland to Chicago are considered frequent. This assessment is based on pricing trends observed over a 30-day period. Travelers can often find favorable deals for this route, indicating consistent opportunities for cost-effective travel.

Flights From Portland

To Chicago

Cheap Flights from Portland to Chicago

Q: How long is the flight from Portland to Chicago?

A direct flight from Portland to Chicago typically has a median duration of 4 hours and 10 minutes. For flights with one stop, the median travel time increases to approximately 7 hours and 45 minutes. The distance covered on this route is about 2811 kilometers, contributing to the flight duration.

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Prices updated 1 day ago

461 airlines compared

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Fares are subject to change and may not be available for all dates. (Data last updated Sep 14, 2026.)

Today’s best flight deals from Portland to Chicago

Explore current cheapest deals departing from Portland to Chicago

2026-11-10 – 2026-11-16
PDX - Chicago
72% AI deal score
$290
$225
Round trip
2026-10-20 – 2026-10-27
PDX - Chicago
66% AI deal score
$243
$244
Round trip
2026-10-20 – 2026-11-03
PDX - Chicago
49% AI deal score
$215
$244
Round trip
2026-10-20 – 2026-11-10
PDX - Chicago
49% AI deal score
$206
$244
Round trip
2026-10-20 – 2026-10-21
PDX - Chicago
68% AI deal score
$188
$250
Round trip
2026-10-27 – 2026-11-03
PDX - Chicago
65% AI deal score
$242
$250
Round trip
2026-11-03 – 2026-11-10
PDX - Chicago
69% AI deal score
$289
$250
Round trip
2026-10-27 – 2026-11-10
PDX - Chicago
49% AI deal score
$215
$250
Round trip
2026-10-13 – 2026-10-20
PDX - Chicago
65% AI deal score
$244
$251
Round trip
2026-10-13 – 2026-10-27
PDX - Chicago
49% AI deal score
$215
$251
Round trip

Portland to Chicago: Overview

Insights for flights from Portland to Chicago

Flights from Portland to Chicago cover a distance of 2811 kilometers, classifying this as a medium-haul route. This means you can expect a journey that balances travel time with the opportunity to find competitive fares. New deals appear almost daily for this route, offering frequent opportunities to find cheap flights from Portland to Chicago.

Right now, fares for flights from Portland to Chicago typically range from $305 to $630, with a median price of $397. Current fares are significantly below the typical level, with 1% of recent fares classified as a good price. This indicates a favorable time to consider booking your trip.

When is the cheapest time to fly from Portland to Chicago? The data shows that January is typically the most affordable month, with a median fare of $161. Following closely are February, with a median of $179, and April, with a median of $251. Planning your travel during these months could result in substantial savings.

Most itineraries for this route connect at least once, with only 34.2% of recent fares being direct flights from Portland to Chicago. For connecting itineraries, the typical number of stopovers is 2. This means that while direct options exist, you will likely encounter flights with one or more stops.

How long is the flight from Portland to Chicago? A typical journey, including connections, takes approximately 8 hours and 57 minutes. This duration accounts for the fact that most itineraries involve at least one stopover, making it important to factor in the total travel time when planning your trip.

How much is a round trip from Portland to Chicago

Regular price: $230 - $319

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

The regular price range for flights from Portland to Chicago is $230 to $319. The current lowest deal is $225 with Frontier Airlines, for travel from Nov 10-Nov 16.

now $225

Low $230

High $319

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 $161. The most expensive month is March, with a median price of $442. Prices are generally lower from January to November.

January

Cheapest

Flights from $161

March

Most Expensive

Flights from $442

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Portland to Chicago

Alaska Airlines, Inc.

Last-minute flights going from Portland to Chicago

Tue, Oct 6

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (MDW)

Southwest Airlines

$313

$292

One-way

Sat, Oct 10

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

American Airlines

$189

$269

One-way

Sat, Oct 10

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

American Airlines

$179

$269

One-way

Sat, Oct 10

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (MDW)

Southwest Airlines

$333

$322

One-way

Tue, Oct 13

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

Frontier Airlines

$244

$249

One-way

Tue, Oct 13

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

Frontier Airlines

$206

$249

One-way

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

6 nights

Nov 10 - Nov 16

$291 → $227

22%

3 nights

Sep 14 - Sep 17

$434 → $392

10%

6 nights

Nov 4 - Nov 10

$316 → $279

12%

2 nights

Sep 18 - Sep 20

$425 → $399

Popular Airports to fly from Portland to Chicago

Portland - Chicago route insights

💸 Price insights

Recent fares are below the typical level

Recent fares from Portland to Chicago are below the typical level at $225.

📅 Best time to fly

January offers the lowest median prices

Historically, January is the cheapest month to fly, with a median price of $161.

⏱️ Flight duration

Median flight time is 8h 57m

The median flight time from Portland to Chicago is 8 hours and 57 minutes.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights make up 65.8% of routes, with a median of 2 stopovers.

🏆 Airline highlight

Frontier Airlines offers a deal at $225

Frontier Airlines has a recent deal for $225 from Portland to Chicago.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Portland to Chicago appear frequently, typically every 30 days.

Portland main airports to depart from

Portland International (PDX)

Cheapest

Portland International Airport is a convenient departure point for flights from Portland to Chicago.

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

💸 Flights from ~$240

Chicago main airports to arrive at

Chicago Rockford International (RFD)

Cheapest

Consider Chicago Rockford International for potentially cheaper flights to Chicago from Portland.

📍 ~126 km from Chicago city center (reachable by car)

💸 Flights from ~$240

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 train or car)

💸 Flights from ~$314

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

Dec 14

Chicago, United States

90% AI deal score

$1,890

$950

Save $940

Alaska Airlines, Inc.

Business Class

From PDX

Elite

Jan 30

Chicago, United States

89% AI deal score

$1,680

$905

Save $775

Alaska Airlines, Inc.

Business Class

From PDX

Elite

Nov 16

Chicago, United States

89% AI deal score

$1,665

$914

Save $751

Alaska Airlines, Inc.

Business Class

From PDX

Elite

Dec 14

Chicago, United States

89% AI deal score

$1,935

$978

Save $957

Alaska Airlines, Inc.

Business Class

From PDX

Elite

Nov 09

Chicago, United States

89% AI deal score

$1,785

$988

Save $797

Alaska Airlines, Inc.

Business Class

From PDX

Elite

Nov 11

Chicago, United States

89% AI deal score

$1,882

$994

Save $888

Alaska Airlines, Inc.

Business Class

From PDX

Elite

Nov 10

Chicago, United States

89% AI deal score

$1,830

$994

Save $836

Alaska Airlines, Inc.

Business Class

From PDX

Elite

Dec 18

Chicago, United States

89% AI deal score

$1,910

$1,000

Save $910

Alaska Airlines, Inc.

Business Class

From PDX

Elite

Jan 05

Chicago, United States

88% AI deal score

$1,588

$909

Save $679

Alaska Airlines, Inc.

Business Class

From PDX

Elite

Nov 16

Chicago, United States

88% AI deal score

$1,659

$949

Save $710

Alaska Airlines, Inc.

Business Class

From PDX

Elite

Nov 09

Chicago, United States

88% AI deal score

$1,668

$972

Save $696

Alaska Airlines, Inc.

Business Class

From PDX

Elite

Nov 10

Chicago, United States

88% AI deal score

$1,663

$978

Save $685

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the optimal time to purchase tickets for flights from Portland to Chicago is typically 14-27 days before departure. During this period, the average price for a ticket is around $266. Prices tend to be higher when booking further out, with flights booked 60+ days in advance averaging $698. Conversely, waiting until 0-6 days before departure usually sees prices rise to an average of $320.

Across the trailing quarter, a good price for a flight from Portland to Chicago is considered to be $305 or less. The median price for this route historically stands at $397. Travelers can expect to pay around $630 for flights in the higher price range. These figures are based on pricing trends observed over a 90-day window.

Historically, January is often the most affordable month to fly from Portland to Chicago, with a median price of $161. February also offers competitive prices, with a median of $179. While April shows a median of $251, it was also the most expensive month in the trailing 270 days. The annual median price for this route is $397.

Related routes

More routes from Portland

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Flights to Chicago from other cities

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Portland to Chicago: Overview

Insights for flights from Portland to Chicago

How much is a round trip from Portland to Chicago

Regular price: $230 - $319

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

The regular price range for flights from Portland to Chicago is $230 to $319. The current lowest deal is $225 with Frontier Airlines, for travel from Nov 10-Nov 16.

now $225

Low $230

High $319

The cheapest time to fly from Portland to Chicago

January

Cheapest

Flights from $161

March

Most Expensive

Flights from $442

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Portland to Chicago

Alaska Airlines, Inc.

Last-minute flights going from Portland to Chicago

Tue, Oct 6

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (MDW)

Southwest Airlines

$313

$292

One-way

Sat, Oct 10

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

American Airlines

$189

$269

One-way

Sat, Oct 10

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

American Airlines

$179

$269

One-way

Sat, Oct 10

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (MDW)

Southwest Airlines

$333

$322

One-way

Tue, Oct 13

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

Frontier Airlines

$244

$249

One-way

Tue, Oct 13

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

Frontier Airlines

$206

$249

One-way

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

6 nights

Nov 10 - Nov 16

$291 → $227

22%

3 nights

Sep 14 - Sep 17

$434 → $392

10%

6 nights

Nov 4 - Nov 10

$316 → $279

12%

2 nights

Sep 18 - Sep 20

$425 → $399

Popular Airports to fly from Portland to Chicago

Portland - Chicago route insights

💸 Price insights

Recent fares are below the typical level

Recent fares from Portland to Chicago are below the typical level at $225.

📅 Best time to fly

January offers the lowest median prices

Historically, January is the cheapest month to fly, with a median price of $161.

⏱️ Flight duration

Median flight time is 8h 57m

The median flight time from Portland to Chicago is 8 hours and 57 minutes.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights make up 65.8% of routes, with a median of 2 stopovers.

🏆 Airline highlight

Frontier Airlines offers a deal at $225

Frontier Airlines has a recent deal for $225 from Portland to Chicago.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Portland to Chicago appear frequently, typically every 30 days.

Portland main airports to depart from

Portland International (PDX)

Cheapest

Portland International Airport is a convenient departure point for flights from Portland to Chicago.

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

💸 Flights from ~$240

Chicago main airports to arrive at

Chicago Rockford International (RFD)

Cheapest

Consider Chicago Rockford International for potentially cheaper flights to Chicago from Portland.

📍 ~126 km from Chicago city center (reachable by car)

💸 Flights from ~$240

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

88% AI deal score

$1,663

$978

Save $685

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Chicago

Cheap Flights from Portland to Chicago

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 below the typical level

January offers the lowest median prices

Median flight time is 8h 57m

Connecting flights are dominant

Frontier Airlines offers a deal at $225

Deals are frequent on this route

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

Dec 14

Jan 30

Nov 16

Dec 14

Nov 09

Nov 11

Nov 10

Dec 18

Jan 05

Nov 16

Nov 09

Nov 10

Frequently Asked Questions About Flights to Chicago

When should I buy Portland to Chicago tickets?

How much should a flight from Portland to Chicago cost?

What's the best month to fly from Portland to Chicago?

What percentage of Portland to Chicago flights are direct?

How long is the flight from Portland to Chicago?

Are there frequently good prices on flights from Portland to Chicago?

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 below the typical level

January offers the lowest median prices

Median flight time is 8h 57m

Connecting flights are dominant

Frontier Airlines offers a deal at $225

Deals are frequent on this route

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

Dec 14

Jan 30

Nov 16

Dec 14

Nov 09

Nov 11

Nov 10

Dec 18

Jan 05

Nov 16

Nov 09

Nov 10

Frequently Asked Questions About Flights to Chicago

When should I buy Portland to Chicago tickets?

How much should a flight from Portland to Chicago cost?

What's the best month to fly from Portland to Chicago?