Cheap flights from Portland (PDX) to Chicago (CHI) from $42

Friday is generally a great day to depart. Flying on this day could help you save up to 30%.

Travelers have found it’s best to book a flight 61 days in advance to save up to 42% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 61 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Portland to Chicago 1-2 weeks in advance for as low as $554, or $711 for flights within the next 24 hours.

Due to multiple factors, expect to potentially pay more when booking in July. For low rates, January can be a great choice for travel to Chicago. Flights to Chicago from Portland in January are about $455 on average during January, but can be found for as low as $199.

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 40% on your trip compared to booking a flight in the morning.

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 14 outbound flights to Chicago per day. 6 airlines have flights to Chicago from Portland on a regular basis.

Yes, there are multiple flights from Portland to Chicago for under $100. The cheapest flight booked recently is on Frontier for just $88, but on average you can expect to pay $112.

Cheapflights has at least 20 direct flights from Portland to Chicago under $200. A good price for a nonstop flight from Portland to Chicago is less than $243.

There are currently 20+ open flights from Portland to Chicago within the next 7 days for less than $200.

Days when nonstop flights are available for this flight are: Sunday, Tuesday, Wednesday, Thursday, Friday, Saturday.

Travelers can expect 14 flights from Portland to Chicago on average per day.
Morning (6am - Noon) - 50% of flight departures
Afternoon (Noon - 6pm) - 50% of flight departures

For as low as $88, Frontier can have you in Chicago from Portland in 11h 45m. Airlines will cover a distance of 1744 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

Frontier, at $88, was found to be the cheapest airline from Portland to Chicago. An alternate airline flying to your destination would be Spirit Airlines. You may be able to fly from Portland to Chicago for 80% less than the average price by searching for these airlines.

$42 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and Alaska Airlines, with prices starting from $63 and $79, respectively.

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.

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

Consider United Airlines (91%), Brussels Airlines (91%) or Aer Lingus (90%) when booking your flight. These represent the most reliable airlines when flying from Portland to Chicago.

While on average a flight from Portland to Chicago is generally $965, our data shows the cheapest flight currently is $98. When looking at the most popular route, (Portland - Chicago O'Hare Intl), you can expect to pay $116 for that flight.

Portland Airport is PDX and Chicago O'Hare Intl Airport is ORD. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.

Deals for Portland to Chicago flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Portland to Chicago for you. Better yet — we are completely free to use.

Yes! Cheapflights helps users easily find flights from Portland to Chicago with no change fees.

Of course! You can now track prices for flights from Portland to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and make a flight search when you’re ready to set up your price alert.