Can I fly direct from Chicago to Portland?

Yes, direct flights from Chicago to Portland are frequently available. Historically, approximately 61.8% of flights on this route have been direct. For journeys that include stopovers, travelers typically experience 2 stops. This indicates a strong presence of non-stop options for this route across the trailing 90 days.

How many hours is the flight from Chicago to Portland?

The typical direct flight from Chicago to Portland has a duration of 4 hours and 26 minutes. For flights with one stop, the median travel time is significantly longer, averaging 8 hours and 35 minutes. The distance covered on this route is approximately 2792 kilometers. Travelers should account for these differences when planning their journey.

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

Historically, deals for flights from Chicago to Portland are frequent. This route consistently shows opportunities for savings across the trailing 30 days. Setting a price alert can be beneficial for travelers seeking to secure a good fare. Given the frequent availability of deals, alerts can help identify optimal booking times.

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 2 days ago

405 airlines compared

80%+ AI score for best value

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

Today’s best flight deals from Chicago to Portland

Explore current cheapest deals departing from Chicago to Portland

2026-10-08 – 2026-10-13
CHI - Portland
67% AI deal score
$257
$247
Round trip
2026-09-01 – 2026-09-08
CHI - Portland
69% AI deal score
$284
$248
Round trip
2026-10-01 – 2026-10-05
CHI - Portland
67% AI deal score
$259
$248
Round trip
2026-09-05 – 2026-09-12
CHI - Portland
69% AI deal score
$284
$249
Round trip
2026-09-23 – 2026-09-26
CHI - Portland
70% AI deal score
$303
$249
Round trip
2026-09-05 – 2026-09-08
CHI - Portland
70% AI deal score
$300
$249
Round trip
2026-10-13 – 2026-10-17
CHI - Portland
67% AI deal score
$259
$250
Round trip
2026-10-20 – 2026-11-16
CHI - Portland
48% AI deal score
$220
$251
Round trip
2026-09-01 – 2026-09-07
CHI - Portland
69% AI deal score
$284
$254
Round trip
2026-09-02 – 2026-09-10
CHI - Portland
67% AI deal score
$272
$254
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, fares are near the typical level for this route. About 7% of recent fares from Chicago to Portland were classified as a good price, indicating that competitive deals can be found.

When is the cheapest time to fly from Chicago to Portland? The most affordable months to fly are typically April, with a median fare of $251, followed by May at $261, and November at $279. Planning your trip during these months could lead to more significant savings.

A typical journey from Chicago to Portland takes about 4h 26m, including connections. While a meaningful share of itineraries are non-stop, the rest connect at least once. For connecting flights, the typical number of connections is 2, which extends the overall travel time.

This route covers a distance of 2792 kilometers, classifying it as a medium-haul flight. This means you can expect a journey that is longer than a short domestic hop but generally shorter than an international long-haul trip.

How much is a round trip from Chicago to Portland

Regular price: $211 - $307

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

The regular price range for flights from Chicago to Portland is typically between $211 and $307. The current lowest deal is $247 with Frontier Airlines for travel from Oct 8-Oct 13.

now $247

Low $211

High $307

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 this route 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

Mon, Jul 27

⌛ Last-Minute

ORD - Portland

Chicago (ORD) - Portland (PDX)

Frontier Airlines

$481

$382

One-way

Mon, Jul 27

⌛ Last-Minute

ORD - Portland

Chicago (ORD) - Portland (PDX)

Frontier Airlines

$473

$382

One-way

Tue, Jul 28

⌛ Last-Minute

ORD - Portland

Chicago (ORD) - Portland (PDX)

Frontier Airlines

$471

$330

One-way

Sat, Aug 1

⌛ Last-Minute

ORD - Portland

Chicago (ORD) - Portland (PDX)

Alaska Airlines, Inc.

$391

$359

One-way

Sat, Aug 1

⌛ Last-Minute

ORD - Portland

Chicago (ORD) - Portland (PDX)

Alaska Airlines, Inc.

$472

$415

One-way

Mon, Aug 3

⌛ Last-Minute

RFD - Portland

Chicago (RFD) - Portland (PDX)

Allegiant Air

$455

$389

One-way

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

4 nights

Aug 13 - Aug 17

$608 → $339

44%

3 nights

Jul 28 - Jul 31

$471 → $330

30%

1 night

Aug 26 - Aug 27

$431 → $305

29%

2 nights

Aug 20 - Aug 22

$431 → $305

29%

Popular Airports to fly from Chicago to Portland

Chicago - Portland route insights

💸 Price insights

Recent fares are near the typical level

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

📅 Best time to fly

Fly in November for the best prices

Historically, November is the cheapest month to fly, with a median price of $258.

⏱️ Flight duration

Direct flights take 4h 26m

The median flight time for direct routes is 4h 26m, while connecting flights average 10h 32m.

✈️ Airlines & availability

Direct flights are available

61.8% of recent flights from Chicago to Portland are direct, with Alaska Airlines, Inc. offering deals.

🏆 Airline highlight

Alaska Airlines, Inc. offers direct flights

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

🎯 Booking tip

Deals are frequent on this route

Deals on flights from Chicago to Portland are frequent, appearing often over 30 days.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport offers flights to Portland, providing a convenient departure option from Chicago.

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

💸 Flights from ~$193

Chicago Midway International (MDW)

Chicago Midway International Airport is an option for flights to Portland from the Chicago area.

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

💸 Flights from ~$226

Chicago Rockford International (RFD)

Chicago Rockford International Airport provides an alternative departure point for flights to Portland.

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

💸 Flights from ~$299

Portland main airports to arrive at

Portland International (PDX)

Cheapest

Portland International Airport is a convenient arrival choice for travelers heading to Portland.

📍 ~10 km from Portland (reachable by car)

💸 Flights from ~$194

Airports nearby Portland used as alternative

Seattle–Tacoma International (SEA)

Cheapest

Seattle–Tacoma International offers significantly more flight options than Portland, often with competitive international pricing.

📍 ~220 km from Portland (reachable by car or rail).

💸 Flights from ~$162

Business & First Class Flight Deals to Portland

73% AI deal score

$950

$887

Save $63

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 7-13 days out typically sees an average price of $307, while waiting until 0-6 days before departure can result in an average price of $377. For the trailing 90 days, prices generally increase significantly for bookings made 60+ days out, averaging $649.

Based on data from the trailing 90 days, a good price for a flight from Chicago to Portland is considered to be $303 or less. The median price for this route historically stands at $315. Prices can go up to $412 or more for the higher end of fares. Travelers should aim for prices at or below the $303 threshold to secure a favorable deal.

Historically, the cheapest months to fly from Chicago to Portland are April, with a median price of $251, and May, with a median price of $261. November also offers competitive prices, with a median of $279. Across the trailing quarter, the annual median price for this route is $315. Travelers looking for lower fares should consider these months.

Related routes

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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: $211 - $307

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

The regular price range for flights from Chicago to Portland is typically between $211 and $307. The current lowest deal is $247 with Frontier Airlines for travel from Oct 8-Oct 13.

now $247

Low $211

High $307

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