Can I fly direct from Chicago to Portland?

Yes, direct flights are available from Chicago to Portland. Historically, approximately 27.5% of flights on this route have been direct. For flights that include stopovers, the median number of stopovers is typically 2. Travelers have options for both direct and connecting services.

How many hours is the flight from Chicago to Portland?

The typical direct flight from Chicago to Portland takes approximately 4 hours and 34 minutes. This corresponds to a median duration of 274 minutes. For flights with one stop, the median duration is considerably longer, averaging around 10 hours and 15 minutes, or 615 minutes. The distance covered is 2792 kilometers.

Should I set a price alert for Chicago to Portland flights?

Historically, flights from Chicago to Portland are frequently discounted. This route is classified as one where deals appear often. Setting a price alert can be beneficial for travelers seeking to find lower fares.

Flights From Chicago

To Portland

Cheap Flights from Chicago to Portland

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

Deals from

Chicago

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

Prices updated 7 days ago

483 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Oct 26, 2026.)

Today’s best flight deals from Chicago to Portland

Explore current cheapest deals departing from Chicago to Portland

2027-01-12 – 2027-01-19
CHI - Portland
48% AI deal score
$203
$236
Round trip
2026-12-10 – 2027-01-07
CHI - Portland
70% AI deal score
$276
$237
Round trip
2027-01-12 – 2027-02-09
CHI - Portland
47% AI deal score
$177
$238
Round trip
2027-02-02 – 2027-02-09
CHI - Portland
67% AI deal score
$252
$240
Round trip
2027-02-02 – 2027-02-18
CHI - Portland
50% AI deal score
$229
$240
Round trip
2027-02-09 – 2027-02-18
CHI - Portland
66% AI deal score
$246
$241
Round trip
2027-02-02 – 2027-03-02
CHI - Portland
50% AI deal score
$226
$242
Round trip
2027-02-02 – 2027-02-23
CHI - Portland
50% AI deal score
$227
$242
Round trip
2026-12-08 – 2027-01-07
CHI - Portland
69% AI deal score
$276
$244
Round trip
2027-01-12 – 2027-01-24
CHI - Portland
48% AI deal score
$185
$245
Round trip

Chicago to Portland: Overview

Insights for flights from Chicago to Portland

For travelers looking for cheap flights from Chicago to Portland, fares typically range from $403–$911, with a median of $582. Right now, current fares are above the typical level. However, new deals appear almost daily, offering opportunities to find better prices.

When is the cheapest time to fly from Chicago to Portland? The data indicates that May is the most affordable month, with a median fare of $180. Following May, July offers a median fare of $343, and February presents a median of $351, making these months generally more budget-friendly for this route.

A typical journey from Chicago to Portland takes approximately 4h 34m, including connections. Most itineraries connect at least once, with the median number of stopovers for connecting flights being 2. Non-stop flights also have a median duration of 4h 34m, while connecting flights typically take around 12h 50m.

The route from Chicago to Portland covers a distance of 2792 kilometers. This classifies it as a medium-haul flight, meaning you can expect a journey that balances distance with travel time, often involving a single day of travel.

How much is a round trip from Chicago to Portland

Regular price: $257 - $393

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

The regular price range for flights from Chicago to Portland is typically between $257 and $393. Currently, the lowest deal found is $247 with Allegiant Air, for travel from February 3 to February 9.

now $247

Low $257

High $393

The cheapest time to fly from Chicago to Portland

The cheapest month to fly from Chicago to Portland is May, with a median price of $180. The most expensive month is March, with a median price of $853. Prices are generally lower from January to September.

May

Cheapest

Flights from $180

March

Most Expensive

Flights from $853

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to Portland

Alaska Airlines, Inc.

Last-minute flights going from Chicago to Portland

Tue, Oct 27

⌛ Last-Minute

MDW - Portland

Chicago (MDW) - Portland (PDX)

Southwest Airlines

$382

$515

One-way

Wed, Oct 28

⌛ Last-Minute

MDW - Portland

Chicago (MDW) - Portland (PDX)

Southwest Airlines

$382

$530

One-way

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

7 nights

Dec 3 - Dec 10

$335 → $248

26%

2 nights

Dec 4 - Dec 6

$357 → $294

18%

2 nights

Dec 11 - Dec 13

$357 → $294

18%

6 nights

Feb 3 - Feb 9

$305 → $247

19%

Popular Airports to fly from Chicago to Portland

Chicago - Portland route insights

💸 Price insights

Recent fares are below the typical level.

Recent fares from Chicago to Portland are below the typical level, with a median price of $582.

📅 Best time to fly

May is historically the cheapest month to fly.

Historically, the cheapest month to fly from Chicago to Portland is May, with a median price of $180.

⏱️ Flight duration

Direct flights average 4h 34m.

The median flight duration for direct flights from Chicago to Portland is 4 hours 34 minutes.

✈️ Airlines & availability

Connecting flights are dominant on this route.

Connecting flights make up 72.5% of recent bookings, with a median of 2 stopovers.

🏆 Airline highlight

Alaska Airlines, Inc. offers direct flights.

Alaska Airlines, Inc. has offered direct flights from Chicago to Portland recently.

🎯 Booking tip

Deals are frequent for this route.

Deals for flights from Chicago to Portland are frequent, appearing every 30 days.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport offers the cheapest flights from Chicago to Portland.

📍 ~25 km from Chicago (reachable by car or train)

💸 Flights from ~$295

Portland main airports to arrive at

Portland International (PDX)

Cheapest

Portland International Airport is a convenient arrival choice for flights to Portland.

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

💸 Flights from ~$205

Airports nearby Portland used as alternative

Seattle–Tacoma International (SEA)

Cheapest

Seattle–Tacoma International offers significantly more flight options and often more competitive pricing than PDX.

📍 ~230 km from Portland (reachable by car or train)

💸 Flights from ~$289

Business & First Class Flight Deals to Portland

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

Elite

Best Elite deals to Portland

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

From ORD

Elite

Dec 05

Portland, United States

83% AI deal score

$1,063

$841

Save $222

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 05

Portland, United States

83% AI deal score

$1,071

$841

Save $230

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 12

Portland, United States

82% AI deal score

$1,070

$846

Save $224

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 10

Portland, United States

82% AI deal score

$1,025

$846

Save $179

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 12

Portland, United States

82% AI deal score

$1,062

$846

Save $216

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 10

Portland, United States

82% AI deal score

$1,054

$846

Save $208

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 12

Portland, United States

81% AI deal score

$1,047

$869

Save $178

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 09

Portland, United States

77% AI deal score

$1,021

$869

Save $152

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 15

Portland, United States

77% AI deal score

$1,077

$892

Save $185

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 05

Portland, United States

76% AI deal score

$949

$841

Save $108

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 05

Portland, United States

75% AI deal score

$941

$841

Save $100

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 10

Portland, United States

75% AI deal score

$955

$869

Save $86

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Portland

Historically, the best prices for flights from Chicago to Portland are found when booking 28-59 days in advance. During this period, the average price is around $273. Booking within 0-6 days of departure typically sees prices rise to about $789, while booking 7-13 days out can result in an average price of $1044. Even booking 60+ days out tends to be more expensive, with an average price of $840.

Across the trailing quarter, a good price for a flight from Chicago to Portland is considered to be $403 or less. The median price for this route has been $582. Prices can go up to $911 or more, representing the higher end of the price spectrum in the trailing 90 days.

Historically, May has been the cheapest month to fly from Chicago to Portland, with a median price of $180. July and February also show relatively lower median prices at $343 and $351, respectively. The annual median price for this route is $582, indicating that these months offer significant savings.

Related routes

More routes from Chicago

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Flights to Portland from other cities

Flights from Copenhagen to Portland Flights from Dallas to Portland Flights from Denver to Portland Flights from Edinburgh to Portland Flights from Frankfurt to Portland Flights from Fresno to Portland Flights from Houston to Portland Flights from Las Vegas to Portland Flights from Lisbon to Portland Flights from London to Portland Flights from Los Angeles to Portland Flights from Madrid to Portland

Chicago to Portland: Overview

Insights for flights from Chicago to Portland

How much is a round trip from Chicago to Portland

Regular price: $257 - $393

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

The regular price range for flights from Chicago to Portland is typically between $257 and $393. Currently, the lowest deal found is $247 with Allegiant Air, for travel from February 3 to February 9.

now $247

Low $257

High $393

The cheapest time to fly from Chicago to Portland

May

Cheapest

Flights from $180

March

Most Expensive

Flights from $853

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to Portland

Alaska Airlines, Inc.

Last-minute flights going from Chicago to Portland

Tue, Oct 27

⌛ Last-Minute

MDW - Portland

Chicago (MDW) - Portland (PDX)

Southwest Airlines

$382

$515

One-way

Wed, Oct 28

⌛ Last-Minute

MDW - Portland

Chicago (MDW) - Portland (PDX)

Southwest Airlines

$382

$530

One-way

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

7 nights

Dec 3 - Dec 10

$335 → $248

26%

2 nights

Dec 4 - Dec 6

$357 → $294

18%

2 nights

Dec 11 - Dec 13

$357 → $294

18%

6 nights

Feb 3 - Feb 9

$305 → $247

19%

Popular Airports to fly from Chicago to Portland

Chicago - Portland route insights

💸 Price insights

Recent fares are below the typical level.

Recent fares from Chicago to Portland are below the typical level, with a median price of $582.

📅 Best time to fly

May is historically the cheapest month to fly.

Historically, the cheapest month to fly from Chicago to Portland is May, with a median price of $180.

⏱️ Flight duration

Direct flights average 4h 34m.

The median flight duration for direct flights from Chicago to Portland is 4 hours 34 minutes.

✈️ Airlines & availability

Connecting flights are dominant on this route.

Connecting flights make up 72.5% of recent bookings, with a median of 2 stopovers.

🏆 Airline highlight

Alaska Airlines, Inc. offers direct flights.

Alaska Airlines, Inc. has offered direct flights from Chicago to Portland recently.

🎯 Booking tip

Deals are frequent for this route.

Deals for flights from Chicago to Portland are frequent, appearing every 30 days.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport offers the cheapest flights from Chicago to Portland.

📍 ~25 km from Chicago (reachable by car or train)

💸 Flights from ~$295

Portland main airports to arrive at

Portland International (PDX)

Cheapest

Portland International Airport is a convenient arrival choice for flights to Portland.

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

💸 Flights from ~$205

Airports nearby Portland used as alternative

Seattle–Tacoma International (SEA)

Cheapest

Seattle–Tacoma International offers significantly more flight options and often more competitive pricing than PDX.

Portland, United States

75% AI deal score

$955

$869

Save $86

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Portland

Cheap Flights from Chicago to Portland

Today’s best flight deals from Chicago to Portland

Chicago to Portland: Overview

Insights for flights from Chicago to Portland

How much is a round trip from Chicago to Portland

The cheapest time to fly from Chicago to Portland

Direct flights from Chicago to Portland

Last-minute flights going from Chicago to Portland

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

Popular Airports to fly from Chicago to Portland

Chicago - Portland route insights

Recent fares are below the typical level.

May is historically the cheapest month to fly.

Direct flights average 4h 34m.

Connecting flights are dominant on this route.

Alaska Airlines, Inc. offers direct flights.

Deals are frequent for this route.

Chicago main airports to depart from

Portland main airports to arrive at

Airports nearby Portland used as alternative

Business & First Class Flight Deals to Portland

Best Elite deals to Portland

Dec 05

Dec 05

Dec 12

Dec 10

Dec 12

Dec 10

Dec 12

Dec 09

Dec 15

Dec 05

Dec 05

Dec 10

Frequently Asked Questions About Flights to Portland

How early should I book Chicago to Portland flights to get the cheapest price?

What is a good price for a flight from Chicago to Portland?

When is the cheapest time of year to fly from Chicago to Portland?

Can I fly direct from Chicago to Portland?

How many hours is the flight from Chicago to Portland?

Should I set a price alert for Chicago to Portland flights?

Related routes

More routes from Chicago

Flights to Portland from other cities

Chicago to Portland: Overview

Insights for flights from Chicago to Portland

How much is a round trip from Chicago to Portland

The cheapest time to fly from Chicago to Portland

Direct flights from Chicago to Portland

Last-minute flights going from Chicago to Portland

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

Popular Airports to fly from Chicago to Portland

Chicago - Portland route insights

Recent fares are below the typical level.

May is historically the cheapest month to fly.

Direct flights average 4h 34m.

Connecting flights are dominant on this route.

Alaska Airlines, Inc. offers direct flights.

Deals are frequent for this route.

Chicago main airports to depart from

Portland main airports to arrive at

Airports nearby Portland used as alternative

Business & First Class Flight Deals to Portland

Best Elite deals to Portland

Dec 05

Dec 05

Dec 12

Dec 10

Dec 12

Dec 10

Dec 12

Dec 09

Dec 15

Dec 05

Dec 05

Dec 10

Frequently Asked Questions About Flights to Portland

How early should I book Chicago to Portland flights to get the cheapest price?

What is a good price for a flight from Chicago to Portland?

When is the cheapest time of year to fly from Chicago to Portland?