How long is the flight from Chicago to Portland?

Airlines like United Airlines, Alaska Airlines, and Southwest fly from Chicago to Portland in about 4h 42m. The time it takes to get you to your destination can typically vary by up to 4h 33m. Airlines will cover a distance of 1733 mi. This flight may include one or multiple stops.

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

Our cheapest airline available from Chicago to Portland is Spirit Airlines. Our recent data shows that you can find tickets from as low as $71 on this airline. Additional options worth looking into are Hawaiian Airlines and Frontier, starting at $128 and $138 round-trip. These flights start at 78% lower than the current average price 3 months from now.

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

For one-way options, check prices for Frontier. According to our data, you can fly for as low as $55. Users have also found prices from $88 and $90 on Spirit Airlines and Hawaiian Airlines, respectively.

In terms of precipitation, rainfall in Portland ranges from 0.7 - 5.6 inches per month. November is typically the wettest month, when rainfall can reach 5.6 in. July is typically the driest time to visit Portland when rainfall is around 0.7 in.

If weather is an important factor for your trip to Portland, 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 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 41.0 F).

What are the cheapest flights from Chicago to Portland?

Looking at all options, your cheapest flight can be booked for $118. While the most popular route (Chicago O'Hare Intl - Portland) can be booked for $217 on average, our data indicates $583 when flying from Chicago to Portland.

What are the most reliable airlines from Chicago to Portland?

The top 3 most reliable airlines when flying from Chicago to Portland are Air Canada (66%), United Airlines (65%) and Alaska Airlines (62%).

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

When booking a flight from Chicago to Portland, you may want to consider flying on United Airlines, American Airlines or Alaska Airlines as they are the most popular for this route.

Most accurate provider : When it comes to deals on Chicago-Portland flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Portland flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Portland flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Chicago-Portland flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Portland flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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

For a flight from Chicago to Portland, you will be flying into Portland. Portland (PDX) is just 6.0 mi from the center of the city. Portland is the only Portland airport and it handles 5 inbound flights from Chicago per day. 7 airlines have flights to Portland from Chicago on a regular basis.

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

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

How can I find direct flights from Chicago to Portland?

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

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

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

$119+ Flights from Chicago to Portland

Q: How much does it cost to fly round-trip from Chicago to Portland?

Airfare is below average for this route at the moment. Chicago to Portland flights typically cost between $328 and $573 in January. The cheapest round-trip price found within the last 3 days was $223 on United Airlines (Jan 6-Jan 7).

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Cheapflights Tip: The best prices from Chicago to Portland are usually found in January or September, booked 60 days in advance, depart on a Wednesday or Tuesday and return on a Friday

Cheap flight deals from Chicago to Portland

Cheapest flights from Chicago to Portland
Explore the most affordable flight options available from Chicago to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 16, 2025.

Thu 12/259:08 amORD - PDX

Nonstop4h 50mUnited Airlines

Wed 12/312:35 pmPDX - ORD

1 stop7h 39mUnited Airlines

Deal found 12/16

$307

Fri 12/267:44 pmORD - PDX