What’s the fastest layover option from Portland to Chicago?

Flights via Denver (DEN) have the shortest average one-way travel time for 1-stop routes: 6h 32m.

What’s the top layover airport for flights from Portland to Chicago?

Las Vegas (LAS) – chosen by Cheapflights users on 55% of 1-stop itineraries from Portland to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Portland to Chicago?

Denver (DEN) is the most affordable 1-stop option, with an average round-trip price of $136.

Which airport typically offers the quickest layover for flights from Portland to Chicago?

Flights via Denver (DEN) offer the fastest connection on this route, with an average layover time of 1h 30m.

How long is the flight from Portland to Chicago?

For as low as $231, Delta can have you in Chicago from Portland in 4h 01m. Airlines will cover a distance of 1733 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

What are the cheapest airlines flying from Portland to Chicago round-trip?

Spirit Airlines, at $93, was found to be the cheapest airline from Portland to Chicago.Alternate airlines to your destination round-trip include Frontier and Delta. You may be able to fly from Portland to Chicago for 73% less than the average price by searching for these airlines.

What are the cheapest airlines to fly from Portland to Chicago one-way?

$116 is the cheapest one-way deal found within the past few days, from Alaska Airlines. You may also be able to find cheap deals on Hawaiian Airlines and United Airlines, with prices starting from $116 and $116, respectively.

How far ahead should I book a flight from Portland to Chicago?

Booking 77 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Portland to Chicago?

Currently, August is the cheapest month in which you can book a flight from Portland to Chicago (average of $245). Flying from Portland to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest day to fly from Portland to Chicago?

Travelers seeking maximum savings on their Portland to Chicago flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Portland to Chicago

The most flights from PDX to CHI are scheduled on a Monday (35 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (20 on average).

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What are the most popular routes from Portland to Chicago?

When deciding which route to take from Portland to Chicago consider Portland - Chicago O'Hare Intl, Portland - Chicago Midway or Portland - Chicago Greater Rockford as they are the most popular.

What are the cheapest flights from Portland to Chicago?

While on average a flight from Portland to Chicago is generally $814, our data shows the cheapest flight currently is $114. When looking at the most popular route, (Portland - Chicago O'Hare Intl), you can expect to pay $161 for that flight.

What are the most reliable airlines from Portland to Chicago?

Consider Brussels Airlines (89%), SWISS (83%) or Alaska Airlines (82%) when booking your flight. These represent the most reliable airlines when flying from Portland to Chicago.

What are the most popular airlines that fly from Portland to Chicago?

American Airlines, Alaska Airlines and Delta are the most popular airlines when flying from Portland to Chicago.

What is the cheapest time of day to fly from PDX to CHI?

A simple way to save on the total cost of your ticket is to fly from Portland to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 38% on your trip compared to booking a flight in the morning.

What airport do you fly from for flights from Portland to Chicago?

For a flight from Portland to Chicago, you will be flying from Portland. Portland (PDX) is just 6.0 mi from the center of the city. Portland is the only Portland airport and it handles 28 outbound flights to Chicago per day. 8 airlines have flights to Chicago from Portland on a regular basis.

Can I find deals for flights from Portland to Chicago that include hotel bookings?

Yes. In addition to deals on Portland to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Portland to Chicago?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Chicago.

Can I find deals for business class flights from Portland to Chicago?

Yes. Cheapflights offers flight deals from Portland to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$110+ Cheap Flights from Portland to Chicago

Round-trip from	$195 (Delta)
One-way from	$110 (Expedia)
Popular in	March
Cheapest in	January
Average price	$303
Good round-trip deal	$312 or less
Good one-way deal	$169 or less

Basic Economy allows a personal item only; no carry-on bags unless exceptions apply.

Economy Plus offers extra legroom and is free for MileagePlus Premier members.

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$93	Average$200	FlexibilityNo cancel fee	On-time65%
Frontier	Cheapest$108	Average$268	FlexibilityNo cancel fee	On-time62%
Delta	Cheapest$123	Average$333	FlexibilityNo cancel fee	On-timeN/A
Hawaiian Airlines	Cheapest$125	Average$286	FlexibilityNo cancel fee	On-time85%
American Airlines	Cheapest$195	Average$316	FlexibilityNo cancel fee	On-time71%
Alaska Airlines	Cheapest$200	Average$348	FlexibilityNo cancel fee	On-time75%
United Airlines	Cheapest$226	Average$393	FlexibilityNo cancel fee	On-time69%
Southwest	Cheapest$233	Average$413	FlexibilityNo cancel fee	On-time63%

$110+ Cheap flights from Portland (PDX) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/23. Fares are subject to change and may not be available on all flights or dates of travel.

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Cheapflights Tip: The best prices from Portland to Chicago are usually found in January or August, booked 77 days in advance, depart on a Friday or Thursday and return on a Wednesday

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Find flight deals from Portland to Chicago

Cheapest flights from Portland to ChicagoExplore the most affordable flight options available from Portland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 17, 2025.

Explore the most affordable flight options available from Portland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 17, 2025.

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Use the filters below to find and compare flights from Portland to Chicago that are best for you.

The best insider tips for Portland to Chicago flights

Cheapflights partnered with top experts to bring you the best recommendations for your Portland to Chicago trip

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Best time to book a flight from Portland to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Portland with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Portland to Chicago

How far ahead should I book a flight from Portland to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Portland to Chicago. Price data was last updated on September 12, 2025.

What is the cheapest month to book a flight from Portland to Chicago?

What is the cheapest time of day to fly from PDX to CHI?

Find hourly flight availability from Portland to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 17, 2025.

What is the cheapest day to fly from Portland to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Portland to Chicago. Price data was last updated on September 14, 2025.

Weekly flight availability from Portland to Chicago

What’s the top layover airport for flights from Portland to Chicago?

Share of 1-stop round-trip flights from Portland to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

What’s the cheapest layover airport for flights from Portland to Chicago?

Average round-trip fare for 1-stop flights from Portland to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

What’s the fastest layover option from Portland to Chicago?

Shortest average travel time for 1-stop one-way flights from Portland to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Which airport typically offers the quickest layover for flights from Portland to Chicago?

Average layover duration for 1-stop one-way flights from Portland to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Reviews of airlines servicing Chicago

Read reviews from past customers who have flown Alaska Airlines, Southwest, and United Airlines from Portland to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Portland to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What airport do you fly from for flights from Portland to Chicago?

How long is the flight from Portland to Chicago?

What are the cheapest airlines flying from Portland to Chicago round-trip?

What are the cheapest airlines to fly from Portland to Chicago one-way?

What are the most popular routes from Portland to Chicago?

What are the most reliable airlines from Portland to Chicago?

What are the cheapest flights from Portland to Chicago?

Can I find deals for flights from Portland to Chicago that include hotel bookings?

How can I find direct flights from Portland to Chicago?

Can I find deals for business class flights from Portland to Chicago?

What is the cheapest month to book a flight from Portland to Chicago?

Traveling to a place near Chicago?

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Alternative routes for Portland to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Cheapest flights from Portland to Chicago
Explore the most affordable flight options available from Portland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 17, 2025.