Can I fly direct from Chicago to Portland?

Yes, direct flights are available from Chicago to Portland. Historically, approximately 61.8% of flights on this route have been direct. For journeys that include stopovers, travelers typically experience 2 stopovers before reaching their destination.

How many hours is the flight from Chicago to Portland?

A direct flight from Chicago to Portland typically takes about 4 hours and 26 minutes. This corresponds to a median flight time of 266 minutes. For flights with one stop, the median duration increases to approximately 8 hours and 35 minutes, or 515 minutes.

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

Based on historical trends, deals for flights from Chicago to Portland are considered frequent. This indicates that price fluctuations occur regularly, making it beneficial to monitor prices. Setting a price alert could help travelers secure a more favorable fare for their journey.

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 1 day ago

461 airlines compared

80%+ AI score for best value

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 Chicago to Portland

Explore current cheapest deals departing from Chicago to Portland

2026-10-20 – 2026-10-27
CHI - Portland
65% AI deal score
$244
$249
Round trip
2026-10-20 – 2026-11-10
CHI - Portland
48% AI deal score
$206
$249
Round trip
2026-10-13 – 2026-11-10
CHI - Portland
48% AI deal score
$206
$249
Round trip
2026-10-27 – 2026-11-10
CHI - Portland
48% AI deal score
$217
$249
Round trip
2026-10-13 – 2026-10-27
CHI - Portland
49% AI deal score
$216
$249
Round trip
2026-10-20 – 2026-11-03
CHI - Portland
49% AI deal score
$216
$249
Round trip
2026-10-13 – 2026-11-03
CHI - Portland
48% AI deal score
$206
$249
Round trip
2026-10-27 – 2026-11-03
CHI - Portland
65% AI deal score
$244
$249
Round trip
2026-10-13 – 2026-10-20
CHI - Portland
65% AI deal score
$244
$249
Round trip
2026-10-28 – 2026-10-31
CHI - Portland
67% AI deal score
$189
$250
Round trip

Chicago to Portland: Overview

Insights for flights from Chicago to Portland

For cheap flights from Chicago to Portland, fares typically range from $303–$412, with a median of $315. Right now, current fares are near the typical level for this route. Approximately 7% of recent fares from Chicago to Portland were classified as a good price, indicating that finding deals is possible.

When considering the cheapest time to fly from Chicago to Portland, April stands out with a median fare of $251. Following closely, May also offers competitive prices, with a median of $261. Another favorable month for lower fares is November, where the median price is around $279. These months present the best opportunities for more budget-friendly travel.

A typical journey from Chicago to Portland takes about 4h 26m, including connections. This is a medium-haul route, covering a distance of 2792 kilometers. While a meaningful share of itineraries are non-stop, the rest connect once, with the median connecting itinerary taking 10h 32m. This indicates that while direct flights from Chicago to Portland are available, many travelers will experience a longer journey with layovers.

On this route, 61.8% of recent fares were for non-stop flights, meaning a meaningful share are non-stop, the rest connect once. For itineraries that do include connections, the typical number of stopovers is 2. New deals for this route appear almost daily, offering frequent opportunities to find suitable flights.

How much is a round trip from Chicago to Portland

Regular price: $180 - $330

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

The regular price range for flights from Chicago to Portland is between $180 and $330. The current lowest deal is $267 with American Airlines for travel from Nov 21-Nov 24.

now $267

Low $180

High $330

The cheapest time to fly from Chicago to Portland

The cheapest month to fly from Chicago to Portland is November, with a median price of $258. The most expensive month to fly is October, with a median price of $415. Prices are generally lower from January to December.

November

Cheapest

Flights from $258

October

Most Expensive

Flights from $415

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, Sep 15

⌛ Last-Minute

ORD - Portland

Chicago (ORD) - Portland (PDX)

Alaska Airlines, Inc.

$544

$459

One-way

Wed, Sep 16

⌛ Last-Minute

ORD - Portland

Chicago (ORD) - Portland (PDX)

Frontier Airlines

$486

$400

One-way

Wed, Sep 16

⌛ Last-Minute

ORD - Portland

Chicago (ORD) - Portland (PDX)

Frontier Airlines

$544

$429

One-way

Thu, Sep 17

⌛ Last-Minute

ORD - Portland

Chicago (ORD) - Portland (PDX)

Frontier Airlines

$536

$383

One-way

Thu, Sep 17

⌛ Last-Minute

ORD - Portland

Chicago (ORD) - Portland (PDX)

Frontier Airlines

$431

$388

One-way

Thu, Sep 17

⌛ Last-Minute

ORD - Portland

Chicago (ORD) - Portland (PDX)

Frontier Airlines

$528

$390

One-way

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

2 nights

Sep 17 - Sep 19

$536 → $385

28%

2 nights

Sep 18 - Sep 20

$536 → $393

27%

3 nights

Sep 17 - Sep 20

$528 → $392

26%

4 nights

Sep 17 - Sep 21

$525 → $392

25%

Popular Airports to fly from Chicago to Portland

Chicago - Portland route insights

💸 Price insights

Recent fares are near the typical level

Recent fares for Chicago to Portland are near the typical level of $315.

📅 Best time to fly

Fly in April for the best prices

Historically, April, May, and November offer the lowest median prices, starting at $251.

⏱️ Flight duration

Direct flights average 4h 26m

Direct flights to Portland typically take 4h 26m, while connecting flights average 10h 32m.

✈️ Airlines & availability

61.8% of recent flights are direct

Historically, 61.8% of flights on this route are direct, with frequent deals available.

🏆 Airline highlight

Alaska Airlines offers direct flights

Alaska Airlines, Inc. is one airline that has offered direct flights on this route.

🎯 Booking tip

Good prices are available 7% of the time

Historically, good prices for this route are available 7% of the time.

Chicago main airports to depart from

Chicago Midway International (MDW)

Cheapest

Chicago Midway International offers a convenient departure point for flights from Chicago to Portland.

📍 ~14 km from Chicago city center (reachable by car or train).

💸 Flights from ~$277

Chicago Rockford International (RFD)

Chicago Rockford International is an alternative departure airport for your trip from Chicago to Portland.

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

💸 Flights from ~$277

O Hare International (ORD)

O Hare International is a major airport for flights from Chicago to Portland.

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

💸 Flights from ~$277

Portland main airports to arrive at

Portland International (PDX)

Cheapest

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

📍 ~10 km from Portland (reachable by car)

💸 Flights from ~$277

Airports nearby Portland used as alternative

Seattle–Tacoma International (SEA)

Cheapest

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

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

💸 Flights from ~$193

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 MDW

Elite

Oct 09

Portland, United States

90% AI deal score

$2,766

$1,512

Save $1,254

Porter Airlines, +1

Business Class

From MDW

Elite

Oct 05

Portland, United States

90% AI deal score

$2,853

$1,553

Save $1,300

Porter Airlines, +1

Business Class

From MDW

Elite

Oct 02

Portland, United States

89% AI deal score

$2,746

$1,558

Save $1,188

Porter Airlines, +1

Business Class

From MDW

Elite

Oct 09

Portland, United States

87% AI deal score

$2,704

$1,696

Save $1,008

Porter Airlines, +1

Business Class

From MDW

Elite

Oct 09

Portland, United States

87% AI deal score

$2,730

$1,711

Save $1,019

Porter Airlines, +1

Business Class

From MDW

Elite

Oct 05

Portland, United States

87% AI deal score

$2,763

$1,738

Save $1,025

Porter Airlines, +1

Business Class

From MDW

Elite

Oct 02

Portland, United States

87% AI deal score

$2,729

$1,742

Save $987

Porter Airlines, +1

Business Class

From MDW

Elite

Oct 10

Portland, United States

86% AI deal score

$2,756

$1,746

Save $1,010

Porter Airlines, +1

Business Class

From MDW

Elite

Oct 05

Portland, United States

86% AI deal score

$2,763

$1,753

Save $1,010

Porter Airlines, +1

Business Class

From MDW

Elite

Oct 02

Portland, United States

86% AI deal score

$2,671

$1,757

Save $914

Porter Airlines, +1

Business Class

From MDW

Elite

Oct 02

Portland, United States

86% AI deal score

$2,672

$1,801

Save $871

Porter Airlines, +1

Business Class

From MDW

Elite

Oct 05

Portland, United States

85% AI deal score

$2,702

$1,796

Save $906

Porter Airlines, +1

Business Class

Frequently Asked Questions About Flights to Portland

Historically, the lowest prices for flights from Chicago to Portland are found when booking 14-27 days in advance. During this period, the average price is around $266. Booking within 0-6 days of departure typically sees prices rise to an average of $377. For those booking 60+ days out, the average price can be significantly higher, at $649.

Based on historical data across the trailing quarter, a good price for a flight from Chicago to Portland is considered to be $303 or less. The median price for this route has been $315. Prices tend to increase beyond this point, with 75% of prices observed at $412 or higher.

Historically, the cheapest months to fly from Chicago to Portland include April, with a median price of $251, and May, with a median price of $261. November also offers competitive pricing, with a median of $279. The annual median price for this route is $315, indicating that these months offer significant savings compared to the yearly average.

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: $180 - $330

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

The regular price range for flights from Chicago to Portland is between $180 and $330. The current lowest deal is $267 with American Airlines for travel from Nov 21-Nov 24.

now $267

Low $180

High $330

The cheapest time to fly from Chicago to Portland

November

Cheapest

Flights from $258

October

Most Expensive

Flights from $415

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, Sep 15

⌛ Last-Minute

ORD - Portland

Chicago (ORD) - Portland (PDX)

Alaska Airlines, Inc.

$544

$459

One-way

Wed, Sep 16

⌛ Last-Minute

ORD - Portland

Chicago (ORD) - Portland (PDX)

Frontier Airlines

$486

$400

One-way

Wed, Sep 16

⌛ Last-Minute

ORD - Portland

Chicago (ORD) - Portland (PDX)

Frontier Airlines

$544

$429

One-way

Thu, Sep 17

⌛ Last-Minute

ORD - Portland

Chicago (ORD) - Portland (PDX)

Frontier Airlines

$536

$383

One-way

Thu, Sep 17

⌛ Last-Minute

ORD - Portland

Chicago (ORD) - Portland (PDX)

Frontier Airlines

$431

$388

One-way

Thu, Sep 17

⌛ Last-Minute

ORD - Portland

Chicago (ORD) - Portland (PDX)

Frontier Airlines

$528

$390

One-way

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

2 nights

Sep 17 - Sep 19

$536 → $385

28%

2 nights

Sep 18 - Sep 20

$536 → $393

27%

3 nights

Sep 17 - Sep 20

$528 → $392

26%

4 nights

Sep 17 - Sep 21

$525 → $392

25%

Popular Airports to fly from Chicago to Portland

Chicago - Portland route insights

💸 Price insights

Recent fares are near the typical level

Recent fares for Chicago to Portland are near the typical level of $315.

📅 Best time to fly

Fly in April for the best prices

Historically, April, May, and November offer the lowest median prices, starting at $251.

⏱️ Flight duration

Direct flights average 4h 26m

Direct flights to Portland typically take 4h 26m, while connecting flights average 10h 32m.

✈️ Airlines & availability

61.8% of recent flights are direct

Historically, 61.8% of flights on this route are direct, with frequent deals available.

🏆 Airline highlight

Alaska Airlines offers direct flights

Alaska Airlines, Inc. is one airline that has offered direct flights on this route.

🎯 Booking tip

Good prices are available 7% of the time

Historically, good prices for this route are available 7% of the time.

Chicago main airports to depart from

Chicago Midway International (MDW)

Cheapest

Chicago Midway International offers a convenient departure point for flights from Chicago to Portland.

📍 ~14 km from Chicago city center (reachable by car or train).

💸 Flights from ~$277

Chicago Rockford International (RFD)

Chicago Rockford International is an alternative departure airport for your trip from Chicago to Portland.

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

💸 Flights from ~$277

O Hare International (ORD)

O Hare International is a major airport for flights from Chicago to Portland.

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

💸 Flights from ~$277

Portland main airports to arrive at

Portland International (PDX)

Cheapest

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

📍 ~10 km from Portland (reachable by car)

💸 Flights from ~$277

Airports nearby Portland used as alternative

Seattle–Tacoma International (SEA)

Cheapest

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

Portland, United States

85% AI deal score

$2,702

$1,796

Save $906

Porter Airlines, +1

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 near the typical level

Fly in April for the best prices

Direct flights average 4h 26m

61.8% of recent flights are direct

Alaska Airlines offers direct flights

Good prices are available 7% of the time

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

Oct 09

Oct 05

Oct 02

Oct 09

Oct 09

Oct 05

Oct 02

Oct 10

Oct 05

Oct 02

Oct 02

Oct 05

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 near the typical level

Fly in April for the best prices

Direct flights average 4h 26m

61.8% of recent flights are direct

Alaska Airlines offers direct flights

Good prices are available 7% of the time

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

Oct 09

Oct 05

Oct 02

Oct 09

Oct 09

Oct 05

Oct 02

Oct 10

Oct 05

Oct 02

Oct 02

Oct 05

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?