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Flights Portland — Chicago

Portland
PDX
Chicago
CHI

Cheap flights Portland — Chicago

Below you can see the best deals on flights Portland — Chicago 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 466.

Top 10 cheap flights Portland — Chicago

Direct flights Portland — Chicago

Direct flight options for Portland — Chicago 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 American Airlines — travel time is 4 h 3 min.

Top 10 direct flights Portland — Chicago

About the Portland — Chicago flight

On this page, you can find and book flight tickets for the Portland — Chicago route. The distance between the cities is 2,831 km, and with a flight frequency of 46 flights per week, it is easy to find a convenient departure time.

Flights are operated by United Airlines, American Airlines, and Alaska Airlines. Ticket prices are dynamic, so we recommend using the low-price calendar. The site also provides information on how to get to Portland Airport and how to arrange a transfer once you arrive in Chicago.

Flight schedule Portland — Chicago

The table shows direct flights Portland → Chicago on the selected date. The flight takes approximately 3 h 59 min. Regular flights are operated by United Airlines, American Airlines and Alaska Airlines. Departures from Portland International Airport airports, arrivals at O'Hare International Airport, Chicago Midway International Airport and Midway 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: Portland — Chicago

Below is a calendar of the lowest flight ticket prices for Portland — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from AED 462 in F, and the most expensive are around AED 686 in u. 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

Portland → Chicago, average one-way price

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
JanAED 626lowMayAED 737highSepAED 700medium
FebAED 626lowJunAED 811highOctAED 700medium
MarAED 700mediumJulAED 848highNovAED 774high
AprAED 682mediumAugAED 811highDecAED 811high

Some values are estimated based on seasonality.

When to fly

The climate in Chicago is characterized by distinct seasonality. The warmest month is July, with an average high temperature of 26.5°C, while January is the coldest, with temperatures dropping to -5°C. Rainfall peaks in May, which brings about 126 mm of precipitation.

In terms of savings, the most budget-friendly time to fly is in September, when ticket prices start AED 462, or in August — AED 466. The highest flight prices are typically recorded in April, with the minimum fare starting AED 686.

September is considered the optimal time for a trip: you can enjoy comfortable weather (around 23.5°C) while keeping travel costs to a minimum. It is recommended to avoid planning your flight for May or October if you want to minimize the risk of rainy days.

Temperature · Chicago

Dry and wet days · Chicago

Wind speed and direction · Chicago

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

  • Book your tickets 4–6 weeks before departure to access a wider selection of fares from Alaska Airlines and American Airlines.
  • Check for departures on Tuesday or Wednesday: mid-week flights are often cheaper than those on Friday or Sunday.
  • Use the price trend chart on this page to compare costs for nearby dates and save AED 94 on a single ticket.
  • Carefully check the carry-on baggage rules of your chosen carrier, as "no-baggage" fares are the most common on this route.

Airlines

Major carriers such as United Airlines, American Airlines, and Alaska Airlines provide regular flight services between these cities. There are approximately 46 flights per week, including both direct routes and connecting options. You can find a detailed schedule, flight frequency, and aircraft types for each airline in the list below.

  • United Airlines
    United AirlinesUA
    23x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight PDX → ORD23x/week
      Duration
      4h 10m
      Days
      MTWTFSS
    51.1%Open →
  • American Airlines
    American AirlinesAA
    13x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight PDX → ORD13x/week
      Duration
      4h 16m
      Days
      MTWTFSS
    28.5%Open →
  • Alaska Airlines
    Alaska AirlinesAS
    9x/week
    WebsiteFleet: 31545M pax/year
    • Direct flight PDX → ORD9x/week
      Duration
      4h 7m
      Days
      MTWTFSS
    20.4%Open →

Cities and airports on the Portland — Chicago route

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

Departure

Portland

PDX
United States
About the cityHow to get thereWeatherAll about the country United States
Arrival

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

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Frequently asked questions about the Portland — Chicago flight

How long is the flight from Portland to Chicago?

The distance between the cities is 2,831 km. A direct flight takes an average of about 3 hours and 20 minutes, though the exact time depends on weather conditions and the specific flight.

Which airlines fly on this route?

The main carriers on the Portland — Chicago route are United Airlines, American Airlines, and Alaska Airlines.

Are there direct flights on this route?

Yes, there are approximately 46 flights per week on this route, many of which are direct.

How much is the cheapest ticket?

Flight prices change constantly based on the season and demand. You can always check the current minimum for specific dates in the low-price calendar on this page.

Which airport does the flight arrive at?

Flights from Portland typically arrive at O'Hare International Airport (ORD) or Midway International Airport (MDW), depending on the chosen airline.

Where else you can fly from Portland

SeattleLos AngelesSan FranciscoDenverSalt Lake CitySan JoseNew York CitySan DiegoPhoenixAnchorageLas VegasBoiseVancouverMinneapolisSanta AnaSpokaneSacramentoRedmondHonoluluSanta RosaMedfordAtlantaDallasFresnoOaklandEugeneBurbankBostonRenoHoustonPascoWashington, D.C.AustinPhiladelphiaBozemanCharlotteFairbanksMissoulaPalm SpringsIdaho Falls

Where else you can fly from Chicago

New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverNashvilleLondonIndianapolisSan DiegoMontrealMilwaukeeSt. LouisCharlottePhiladelphiaColumbusKansas CityMiamiPhoenixLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochester
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