What percentage of Portland to Chicago flights are direct?

In the trailing 90 days, approximately 34.2% of flights from Portland to Chicago have historically been direct. For journeys that involve connecting flights, travelers typically experience a median of 2 stopovers. This indicates that while direct options are available, a significant portion of routes will include at least one stop. Travelers should consider this when planning their itinerary.

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

Historically, good prices on flights from Portland to Chicago are considered frequent. This suggests that travelers often have opportunities to find favorable deals for this route. While prices can fluctuate, the consistent availability of good prices indicates that with some flexibility, travelers are likely to secure a reasonable fare for their trip.

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 duration of 4 hours and 10 minutes, covering a distance of 2811 kilometers. Flights with one stop, however, historically take longer, with a median duration of 7 hours and 45 minutes. Travelers should account for these differences in flight time when choosing between direct and connecting options for their journey.

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Deals from

Portland

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Prices updated 2 days ago

405 airlines compared

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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 Portland to Chicago

Explore current cheapest deals departing from Portland to Chicago

2026-09-18 – 2026-09-23
PDX - Chicago
69% AI deal score
$242
$218
Round trip
2026-11-16 – 2026-11-18
PDX - Chicago
76% AI deal score
$286
$222
Round trip
2026-09-19 – 2026-09-22
PDX - Chicago
67% AI deal score
$181
$227
Round trip
2026-10-10 – 2026-10-15
PDX - Chicago
68% AI deal score
$201
$227
Round trip
2026-10-06 – 2026-10-13
PDX - Chicago
67% AI deal score
$250
$238
Round trip
2026-08-18 – 2026-08-26
PDX - Chicago
76% AI deal score
$299
$247
Round trip
2026-12-01 – 2026-12-08
PDX - Chicago
77% AI deal score
$308
$247
Round trip
2026-09-26 – 2026-09-28
PDX - Chicago
65% AI deal score
$244
$248
Round trip
2026-08-23 – 2026-08-24
PDX - Chicago
72% AI deal score
$329
$251
Round trip
2026-09-08 – 2026-09-11
PDX - Chicago
50% AI deal score
$243
$256
Round trip

Portland to Chicago: Overview

Insights for flights from Portland to Chicago

For cheap flights from Portland to Chicago, fares typically range from $305–$630, with a median of $397. Right now, current fares are below the typical level, and only 1% of recent fares were classified as a good price. New deals appear almost daily for this route, suggesting frequent opportunities to find better prices.

When is the cheapest time to fly from Portland to Chicago? The data indicates that January is 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 trip during these months could lead to significant savings.

Most itineraries for flights from Portland to Chicago connect at least once, with only 34.2% of recent fares being non-stop. For connecting itineraries, the typical number of connections is 2. This means you will likely have one or more stops on your journey.

How long is the flight from Portland to Chicago? A typical journey from Portland to Chicago takes 8h 57m, including connections. This duration accounts for the fact that most itineraries on this route involve at least one stopover.

The distance between Portland and Chicago is 2811 km, classifying this as a medium-haul route. This distance typically involves a flight duration that is neither very short nor extremely long, often requiring several hours in the air.

How much is a round trip from Portland to Chicago

Regular price: $199 - $339

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

Regular prices for flights from Portland to Chicago typically range from $199 to $339. The current lowest deal is $248 with Frontier Airlines, for travel from September 14 to September 19.

now $248

Low $199

High $339

The cheapest time to fly from Portland to Chicago

Flights from Portland to Chicago are generally lower priced from January to November. The cheapest month to fly is January, with a median price of $161. The most expensive month is March, with a median price of $442.

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

Sat, Jul 25

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

Alaska Airlines, Inc.

$402

$365

One-way

Wed, Jul 29

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (MDW)

$493

$437

One-way

Sat, Aug 1

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

Alaska Airlines, Inc.

$521

$411

One-way

Mon, Aug 3

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

Frontier Airlines

$441

$347

One-way

Thu, Aug 6

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

Frontier Airlines

$407

$383

One-way

Tue, Aug 11

⌛ Last-Minute

PDX - Chicago

Portland (PDX) - Chicago (ORD)

Frontier Airlines

$353

$264

One-way

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

3 nights

Aug 1 - Aug 4

$521 → $411

21%

3 nights

Aug 3 - Aug 6

$441 → $347

21%

1 night

Aug 11 - Aug 12

$353 → $264

25%

3 nights

Aug 14 - Aug 17

$342 → $262

23%

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, with a median of $397.

📅 Best time to fly

January is historically the cheapest month to fly

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

⏱️ Flight duration

The median flight time is 8h 57m

Flights from Portland to Chicago typically take 8 hours and 57 minutes, covering 2811 km.

✈️ Airlines & availability

Connecting flights are dominant on this route

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

🏆 Airline highlight

Frontier Airlines offers a deal for $248

Frontier Airlines has a recent deal from Portland to Chicago for $248.

🎯 Booking tip

Deals are frequent on this route

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

Portland main airports to depart from

Portland International (PDX)

Cheapest

Portland International Airport is a great option for flights from Portland to Chicago.

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

💸 Flights from ~$202

Chicago main airports to arrive at

Chicago Midway International (MDW)

Cheapest

Consider Chicago Midway International for flights to Chicago, offering a convenient arrival option.

📍 ~17 km from Chicago (reachable by car)

💸 Flights from ~$202

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and direct flight options for Chicago travelers.

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

💸 Flights from ~$254

Business & First Class Flight Deals to Chicago

88% AI deal score

$1,522

$856

Save $666

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 increase significantly outside this window, with tickets purchased 60+ days out averaging $698, and those bought 0-6 days before departure costing approximately $320. Planning your purchase within this sweet spot can lead to considerable savings.

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. Prices can vary, with 75% of tickets observed to be $630 or less. Aiming for a price at or below the $305 threshold typically indicates a favorable deal for your journey.

Historically, January and February are typically the cheapest months to fly from Portland to Chicago, with median prices of $161 and $179 respectively. April also offers competitive pricing, with a median of $251. These months generally present better value compared to the annual median price of $397 for this route. Travelers looking for more affordable options should consider these periods.

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: $199 - $339

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

Regular prices for flights from Portland to Chicago typically range from $199 to $339. The current lowest deal is $248 with Frontier Airlines, for travel from September 14 to September 19.

now $248

Low $199

High $339

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