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Flights from Chicago to Portland

What to know about flights from Chicago to Portland?

The distance between Chicago and Portland is approximately 1,425.81 km. It takes around 2 hours 32 minutes on average to fly from Chicago to Portland. Based on Trip.com's data, travel demand peaks in January.

Cheapest one-way
$113
American Airlines American Airlines CHI-PWM 2h 44m · Nonstop Sat, Oct 17
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Cheapest round-trip
$298
American Airlines American Airlines CHI-PWM 2h 44m · Nonstop Sun, Oct 25 - Thu, Oct 29
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Recommended airlines
American Airlines American Airlines Cheapest · From $113 United Airlines United Airlines Most booked
When to travel
September
Cheapest
January
Peak season for travel
Route details
1,425.81 km
Flight distance
2h 32m
Average flight time

Explore the cheapest one-way and round-trip flights from Chicago to Portland over the next 90 days, with one-way fares from $113 and round-trip from $298. Based on Trip.com's latest 7-day flight data.

      • Cheapest nonstop
        ORD 7:59 PM
        2h 44m
        Nonstop
        PWM 11:43 PM
        Chicago - Portland | Sun, Oct 25 | American Airlines
        PWM 7:00 AM
        3h 4m
        Nonstop
        ORD 9:04 AM
        Portland - Chicago | Thu, Oct 29 | American Airlines
        $298 $512
        42% off
        42% off
        $512 $298
      • ORD 7:59 PM
        2h 44m
        Nonstop
        PWM 11:43 PM
        Chicago - Portland | Tue, Oct 13 | American Airlines
        PWM 11:27 AM
        5h 42m
        1 stop
        ORD 4:09 PM
        Portland - Chicago | Sat, Oct 17 | American Airlines
        $308 $512
        40% off
        40% off
        $512 $308
      • MDW 11:33 AM
        8h 27m
        1 stop
        PWM 9:00 PM
        Chicago - Portland | Tue, Oct 13 | Delta Air Lines
        PWM 4:15 PM
        6h 28m
        1 stop
        ORD 9:43 PM
        Portland - Chicago | Sat, Oct 17 | Delta Air Lines
        $312 $512
        39% off
        39% off
        $512 $312
      • MDW 9:29 AM
        5h 33m
        1 stop
        PWM 4:02 PM
        Chicago - Portland | Sun, Oct 25 | Delta Air Lines
        PWM 6:01 AM
        6h 53m
        1 stop
        MDW 11:54 AM
        Portland - Chicago | Thu, Oct 29 | Delta Air Lines
        $312
        39% off
        $512 $312
      • ORD 6:59 AM
        2h 41m
        Nonstop
        PWM 10:40 AM
        Chicago - Portland | Sun, Oct 11 | United Airlines
        PWM 6:00 AM
        7h 16m
        1 stop
        ORD 12:16 PM
        Portland - Chicago | Fri, Oct 16 | Delta Air Lines
        $317
        38% off
        $512 $317
      • ORD 6:10 PM
        2h 36m
        Nonstop
        PWM 9:46 PM
        Chicago - Portland | Sun, Oct 25 | United Airlines
        PWM 6:01 AM
        6h 53m
        1 stop
        MDW 11:54 AM
        Portland - Chicago | Thu, Oct 29 | Delta Air Lines
        $345
        33% off
        $512 $345
      • ORD 6:10 PM
        2h 36m
        Nonstop
        PWM 9:46 PM
        Chicago - Portland | Tue, Oct 13 | United Airlines
        PWM 6:04 AM
        7h 42m
        1 stop
        ORD 12:46 PM
        Portland - Chicago | Tue, Oct 20 | Delta Air Lines
        $347
        32% off
        $512 $347
      • ORD 8:29 AM
        2h 27m
        Nonstop
        PWM 11:56 AM
        Chicago - Portland | Sun, Nov 22 | American Airlines
        PWM 6:00 AM
        6h 5m
        1 stop
        ORD 11:05 AM
        Portland - Chicago | Thu, Nov 26 | American Airlines
        $348
        32% off
        $512 $348
      • ORD 8:00 PM
        2h 40m
        Nonstop
        PWM 11:40 PM
        Chicago - Portland | Mon, Oct 12 | American Airlines
        PWM 6:00 AM
        7h 52m
        1 stop
        ORD 12:52 PM
        Portland - Chicago | Fri, Oct 16 | American Airlines
        $370
        28% off
        $512 $370
      • ORD 6:10 PM
        2h 36m
        Nonstop
        PWM 9:46 PM
        Chicago - Portland | Mon, Oct 12 | United Airlines
        PWM 4:47 PM
        4h 43m
        1 stop
        ORD 8:30 PM
        Portland - Chicago | Sat, Oct 17 | Delta Air Lines
        $384
        25% off
        $512 $384
      • CHI 1:00 PM
        17h 25m
        1 stop
        PWM 2:00 PM
        Chicago - Portland | Sat, Oct 10 | Normal Airline
        PWM 3:00 PM
        6h
        Nonstop
        CHI 4:00 PM
        Portland - Chicago | Mon, Oct 12 | Normal Airline
        Find more flights
        Find more flights
      • Cheapest nonstop
        ORD 7:59 PM
        2h 44m
        Nonstop
        PWM 11:43 PM
        Chicago - Portland | Sat, Oct 17 | American Airlines
        $113 $279
        59% off
        59% off
        $279 $113
      • ORD 8:00 AM
        2h 28m
        Nonstop
        PWM 11:28 AM
        Chicago - Portland | Fri, Nov 6 | American Airlines
        $209 $279
        25% off
        25% off
        $279 $209
      • ORD 8:30 AM
        2h 28m
        Nonstop
        PWM 11:58 AM
        Chicago - Portland | Sat, Nov 7 | American Airlines
        $209 $279
        25% off
        25% off
        $279 $209
      • ORD 6:06 PM
        4h 53m
        1 stop
        PWM 11:59 PM
        Chicago - Portland | Sat, Oct 17 | United Airlines
        $155
        44% off
        $279 $155
      • RFD 7:56 PM
        20h 55m
        1 stop
        PWM 5:51 PM
        Chicago - Portland | Mon, Nov 2 | Allegiant Air
        $186
        33% off
        $279 $186
      • MDW 9:29 AM
        5h 33m
        1 stop
        PWM 4:02 PM
        Chicago - Portland | Fri, Nov 6 | Delta Air Lines
        $187
        33% off
        $279 $187
      • MDW 6:04 AM
        5h 58m
        1 stop
        PWM 1:02 PM
        Chicago - Portland | Sat, Nov 7 | Delta Air Lines
        $187
        33% off
        $279 $187
      • RFD 9:28 AM
        22h 40m
        1 stop
        PWM 9:08 AM
        Chicago - Portland | Mon, Nov 16 | Allegiant Air
        $187
        33% off
        $279 $187
      • MDW 6:04 AM
        5h 59m
        1 stop
        PWM 1:03 PM
        Chicago - Portland | Tue, Nov 10 | Delta Air Lines
        $187
        33% off
        $279 $187
      • ORD 6:00 PM
        5h 10m
        1 stop
        PWM 12:10 AM
        Chicago - Portland | Sat, Oct 17 | Delta Air Lines
        $189
        32% off
        $279 $189
      • CHI 1:00 PM
        17h 25m
        1 stop
        PWM 2:00 PM
        Chicago - Portland | Sat, Oct 10 | Normal Airline
        Find more flights
        Find more flights

Flight.News
Flights from Chicago to Portland operate an average of 13 times per day over the past 7 days, with a 19.8% on-time departure rate and a 79.0% on-time arrival rate.

Which airlines are the most popular for Chicago to Portland flights?

Direct flights available! Find 1 airlines fly direct from Chicago to Portland, including United Airlines, American Airlines offers the cheapest non stop flights.
United Airlines logo United Airlines
Airlines are determined based on actual purchased flight tickets from Chicago to Portland according to previous 12 months data from Trip.com.

Frequently Asked Questions

  • What are the cheapest flights from Chicago to Portland (CHI-PWM)?

    Based on Trip.com data, American Airlines offers one-way fares as low as $113 on Cheapest nonstop routes (e.g. ORD to PWM on Sat, Oct 17), while American Airlines offers Cheapest nonstop round-trips from $298 departing on Sun, Oct 25 and returning on Thu, Oct 29.
  • At the moment, you can catch a nonstop flight from Chicago to Portland with the following airlines, including: United Airlines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.
  • It takes around 2 hours 32 minutes to fly from Chicago (CHI) to Portland (PWM).
  • By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Chicago to Portland is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.
  • Based on Trip.com data in the past 4 weeks, there is 19 flight per week flying from Chicago to Portland. You can check the weekly schedule for popular airlines on this route below: United Airlines: S/M/T/W/T/F/S -- UA2804 (11:24)
  • To find best deals on flights from Chicago to Portland, you can use various tools on Trip.com:
    · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Sat, Oct 17, with one-way flights priced at just $113.
    · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is American Airlines.
    · Set up price alerts to easily monitor ticket prices without having to check every day.
    · Check Trip.com flight deals and promo codes frequently.
    · Avoid peak season unless you book very early. It seems the peak season for Portland travel is around January.
    · Get exclusive promo codes for Trip.com app users.
  • The cheapest months to fly from Chicago to Portland is September, when demand for travel is lower.
  • After crunching the numbers on our October flight calendar, it's currently cheapest to fly from Chicago to Portland on October 27, 2026 with American Airlines, with prices starting at $225.
  • You can arrive at any of the following airports in Portland: Portland International Jetport (PWM). Flights from O'Hare International Airport to Portland International Jetport (ORD-PWM) are by far the most popular option for this route.
  • The time difference between Portland and Chicago is 1h.
  • Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.
  • Based on Trip.com data for flights departing in the next 30 days, the average one-way fare from Chicago to Portland is $253. Fares vary by travel date, airline and availability.
  • Based on Trip.com data for travel in the next 30 days, the average round-trip fare from Chicago to Portland is $494. The final price depends on the outbound and return dates, airline and fare conditions.
  • Enter Chicago and Portland, choose your travel dates and passengers, then compare flights by price, duration and baggage. Select a fare, review the change and cancellation rules, enter traveler details and complete payment to receive your confirmation.

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Note: Prices shown on this page are estimated lowest price and include all taxes and fees found in the last 24 hours.

Book with no extra fees

Prices displayed in this page are all-inclusive prices (incl. taxes, fuel surcharge, civil aviation development fund, etc) with all fees confirmed before payment. Fees for luggage, meals, WLAN, or other additional services are also included as shown in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page were updated within last 24 hours—even in real-time. The more popular the route, the more precise the data.

Change & Cancellation Policy

Trip.com displays flight cancellation and change policies for each flight ticket during the booking process, including fees and applicable conditions. Please check the following scenarios:
Voluntary cancellation/change:
To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy.
Cancellation/change due to a flight schedule change:
If the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.