Cheap flights from Portland to Chicago (PWM - CHI)

Flight FAQs

From Portland to Chicago

Are flight prices decreasing from Portland to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Portland and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

Which airlines flying from Portland to Chicago have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Portland to Chicago that may be offering flexible cancellation policies are United Airlines, American Airlines, and Delta. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

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 (PWM) is just 2.9 mi from the center of the city. Portland is the only Portland airport and it handles 6 outbound flights to Chicago per day. 5 airlines have flights to Chicago from Portland on a regular basis.

Can I find flights from Portland to Chicago for under $300 on Cheapflights?

Yes, there are multiple flights from Portland to Chicago for under $300. The cheapest flight booked recently is on Multiple Airlines for just $209, but on average you can expect to pay $239.

Are there nonstop flights from Portland to Chicago for under $300 on Cheapflights?

Cheapflights has at least 20 direct flights from Portland to Chicago under $300. A good price for a nonstop flight from Portland to Chicago is less than $308.

Are there last-minute flights available from Portland to Chicago for under $300?

There are currently 20+ open flights from Portland to Chicago within the next 7 days for less than $300.

What days are nonstop flights available from Portland to Chicago?

Nonstop flights can be found on the following days: Monday, Tuesday, Friday.

Is Portland weather warmer or cooler than Chicago?

Temperatures around the 84 °F's can be experienced in July. The weather in Chicago is hotter than in Portland. Plan for potential changes in flight availability as peak weather approaches in this location.

How long is the flight from Portland to Chicago?

A quick flight from Portland to Chicago can take about 2h 40m. United Airlines provides one of the quickest options available for as low as $259. This flight may include one or multiple stops.

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

Cheapflights users have booked flights from Portland to Chicago round-trip from $219. Other airlines that can offer you cheap pricing are American Airlines, from $228, and Delta, from $237. United Airlines is 38% cheaper than the average price of flights available within the next 90 days to this destination.

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

To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $90. United Airlines flights start at $119 while deals on American Airlines start at $137 one-way.