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Flights Chicago — Portland

Chicago
CHI
Portland
PDX

Cheap flights Chicago — Portland

Below you can see the best deals on flights Chicago — Portland for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 15 August, from AED 522.

Top 10 cheap flights Chicago — Portland

Direct flights Chicago — Portland

Direct flight options for Chicago — Portland with no stopovers on upcoming dates. A direct flight is faster and more convenient — especially when travelling with luggage or children.

The fastest direct flight is operated by Alaska Airlines — travel time is 4 h 25 min.

Top 10 direct flights Chicago — Portland

About the Chicago — Portland flight

On this page, you can find and book flights for the ChicagoPortland route. The distance between the cities is 2,831 km, and with up to 46 flights per week, it is easy to find a convenient departure option.

Flights are operated by UA, AA, and AS. Since airfares are dynamic, we recommend using the low-fare calendar and price trend chart to find the best deals for your desired dates.

Flight schedule Chicago — Portland

The table shows direct flights Chicago → Portland on the selected date. The flight takes approximately 4 h 25 min. Regular flights are operated by United Airlines, American Airlines and Alaska Airlines. Departures from O'Hare International Airport, Chicago Midway International Airport and Midway International Airport airports, arrivals at Portland International Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

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Flight ticket prices by day: Chicago — Portland

Below is a calendar of the lowest flight ticket prices for Chicago — Portland by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from AED 381 in F, and the most expensive are around AED 805 in r. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

Chicago → Portland, average one-way price

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
JanAED 717lowMayAED 736mediumSepAED 681low
FebAED 699lowJunAED 883highOctAED 699low
MarAED 754mediumJulAED 901highNovAED 828high
AprAED 754mediumAugAED 699lowDecAED 773medium

Some values are estimated based on seasonality.

When to fly

Weather conditions in Portland vary significantly: August is the warmest month with average temperatures reaching 29.4°C, while January is considered the coldest and rainiest. Precipitation peaks during the winter period, which is worth considering when planning your trip.

According to statistics, the most budget-friendly month to fly is September, when tickets start AED 381. The highest ticket prices from Chicago are observed in June, with costs starting AED 805.

The optimal time for booking is September, which offers a balance between comfortable temperatures and affordable fares. It is best to avoid the winter months due to frequent rain if your goal is outdoor activities.

Temperature · Portland

Dry and wet days · Portland

Wind speed and direction · Portland

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How to get the best deal on a Chicago — Portland ticket

  • Book in advance: For the Chicago — Portland route, the optimal booking window is 4 to 8 weeks before your planned departure.
  • Choose mid-week: Flights on Tuesday or Wednesday are often cheaper than those on Friday or Sunday.
  • Compare baggage policies: Alaska Airlines often offers competitive fares, but be sure to check the carry-on baggage rules.
  • Use the price trend chart: This tool on the page allows you to clearly see which days of the month offer the lowest flight costs.

Airlines

Three major carriers operate on the route from Chicago to Portland: United Airlines, American Airlines, and Alaska Airlines. There are approximately 46 flights per week, the majority of which are direct, non-stop flights. Detailed information on departure times and route options for specific dates can be found in the interactive schedule below.

  • United Airlines
    United AirlinesUA
    22x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight ORD → PDX22x/week
      Duration
      4h 38m
      Days
      MTWTFSS
  • American Airlines
    American AirlinesAA
    15x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight ORD → PDX15x/week
      Duration
      4h 28m
      Days
      MTWTFSS
  • Alaska Airlines
    Alaska AirlinesAS
    9x/week
    WebsiteFleet: 31545M pax/year
    • Direct flight ORD → PDX9x/week
      Duration
      4h 25m
      Days
      MTWTFSS

Cities and airports on the Chicago — Portland route

Flights Chicago — Portland depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport and arrive at Portland International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure airports
Arrival airports

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Frequently asked questions about the Chicago — Portland flight

How long is the flight from Chicago to Portland?

The average travel time for a direct flight over a distance of 2,831 km is approximately 3 hours and 20 minutes.

Which airlines fly this route?

Regular flight service between the cities is provided by United Airlines, American Airlines, and Alaska Airlines.

Are there direct flights?

Yes, there are several direct flights daily on this route, allowing you to reach your destination without any layovers.

How much is the cheapest ticket?

Airfares change constantly; you can check the current minimum rates for your dates in the low-price calendar above.

Which airport does the flight arrive at?

All flights on this route arrive at Portland International Airport (PDX).

When is the best time to buy a ticket?

The most favorable deals are usually available when purchasing 1.5–2 months before the trip, especially for mid-week flights.

Where else you can fly from Chicago

Where else you can fly from Portland

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