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Flights from Portland to Chicago

Hi, I've summed up all the key info for Portland to Chicago flights

Cheapest one-way

$ 99
Frontier Airlines Thu, Sep 17

54% below next 30d avg. ($214)

Cheapest round-trip

$ 248
Delta Air Lines Tue, Oct 13

41% below next 30d avg. ($420)

Fastest flight

4h 14m28m faster than avg. (4h 42m)

Recommended airlines

When to travel

OctoberCheapest month
JulyPeak month

With a lowest one-way fare of $99 , travelers can expect an average price of $214 for upcoming trips, while round-trip tickets start at $248 . Flights typically take around 4h 42m , but the fastest nonstop option completes the journey in just 4h 14m minutes. There are 59 flights weekly on this route. You can arrive at any of the following airports in Chicago: O'Hare International Airport (ORD) , Chicago Midway International Airport (MDW) , and Chicago Rockford International Airport (RFD) . Flights from Portland International Airport to O'Hare International Airport (PDX-ORD) are by far the most popular option for this route. To secure the best rates, booking 40 days in advance is recommended, and the cheapest travel days are Tuesday, Wednesday, and Saturday .

Updated 22h ago · This content is an AI-powered summary based on Trip.com data. Prices and availability are subject to change. Please refer to actual prices, availability, and travel conditions.

Explore the cheapest one-way and round-trip flights from Portland to Chicago over the next 90 days, with one-way fares from $99 and round-trip from $248. Based on Trip.com's latest 7-day flight data.

      • Cheapest nonstop
        PDX 6:01 AM
        4h 15m
        Nonstop
        ORD 12:16 PM
        Portland - Chicago | Sat, Oct 10 | American Airlines
        ORD 9:45 AM
        4h 37m
        Nonstop
        PDX 12:22 PM
        Chicago - Portland | Tue, Oct 13 | American Airlines
        $252 $297
        15% off
        15% off
        $297 $252
      • PDX 6:01 AM
        4h 14m
        Nonstop
        ORD 12:15 PM
        Portland - Chicago | Wed, Sep 30 | American Airlines
        ORD 4:59 PM
        4h 42m
        Nonstop
        PDX 7:41 PM
        Chicago - Portland | Mon, Oct 5 | American Airlines
        $260 $297
        12% off
        12% off
        $297 $260
      • PDX 10:55 PM
        4h 12m
        Nonstop
        ORD 5:07 AM
        Portland - Chicago | Wed, Oct 28 | American Airlines
        ORD 9:45 AM
        4h 37m
        Nonstop
        PDX 12:22 PM
        Chicago - Portland | Fri, Oct 30 | American Airlines
        $270 $297
        9% off
        9% off
        $297 $270
      • PDX 1:05 PM
        8h 45m
        1 stop
        ORD 11:50 PM
        Portland - Chicago | Tue, Oct 13 | Delta Air Lines
        ORD 7:00 AM
        9h 51m
        1 stop
        PDX 2:51 PM
        Chicago - Portland | Wed, Oct 14 | Delta Air Lines
        $248
        16% off
        $297 $248
      • PDX 3:34 PM
        6h 20m
        1 stop
        ORD 11:54 PM
        Portland - Chicago | Sat, Oct 10 | Delta Air Lines
        ORD 7:00 AM
        7h 9m
        1 stop
        PDX 12:09 PM
        Chicago - Portland | Tue, Oct 13 | Delta Air Lines
        $250
        16% off
        $297 $250
      • PDX 1:49 PM
        7h 42m
        1 stop
        ORD 11:31 PM
        Portland - Chicago | Wed, Sep 30 | Delta Air Lines
        MDW 9:45 PM
        4h 25m
        Nonstop
        PDX 12:10 AM
        Chicago - Portland | Mon, Oct 5 |
        $253
        15% off
        $297 $253
      • PDX 12:38 PM
        9h 45m
        1 stop
        ORD 12:23 AM
        Portland - Chicago | Fri, Sep 25 | Frontier Airlines
        ORD 8:55 PM
        16h 41m
        1 stop
        PDX 11:36 AM
        Chicago - Portland | Fri, Oct 2 | Frontier Airlines
        $256
        14% off
        $297 $256
      • PDX 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        Portland - Chicago | Thu, Sep 17 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        PDX 4:00 PM
        Chicago - Portland | Sat, Sep 19 | Normal Airline
        Find more flights
        Find more flights
      • Cheapest nonstop
        PDX 6:01 AM
        4h 14m
        Nonstop
        ORD 12:15 PM
        Portland - Chicago | Sat, Sep 26 | American Airlines
        $249 $274
        9% off
        9% off
        $274 $249
      • PDX 12:38 PM
        9h 45m
        1 stop
        ORD 12:23 AM
        Portland - Chicago | Thu, Sep 17 | Frontier Airlines
        $99 $274
        64% off
        64% off
        $274 $99
      • PDX 11:10 PM
        9h 27m
        1 stop
        ORD 10:37 AM
        Portland - Chicago | Mon, Sep 28 | Delta Air Lines
        $125 $274
        54% off
        54% off
        $274 $125
      • PDX 1:00 PM
        8h 54m
        1 stop
        ORD 11:54 PM
        Portland - Chicago | Sat, Oct 10 | Delta Air Lines
        $125
        54% off
        $274 $125
      • PDX 12:24 PM
        15h 14m
        1 stop
        ORD 5:38 AM
        Portland - Chicago | Sat, Sep 26 | Frontier Airlines
        $182
        34% off
        $274 $182
      • PDX 12:39 PM
        14h 59m
        1 stop
        ORD 5:38 AM
        Portland - Chicago | Mon, Sep 28 | Frontier Airlines
        $200
        27% off
        $274 $200
      • PDX 12:38 PM
        9h 45m
        1 stop
        ORD 12:23 AM
        Portland - Chicago | Fri, Sep 25 | Frontier Airlines
        $203
        26% off
        $274 $203
      • PDX 10:47 AM
        8h 43m
        1 stop
        ORD 9:30 PM
        Portland - Chicago | Sat, Sep 26 | Delta Air Lines
        $249
        9% off
        $274 $249
      • PDX 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        Portland - Chicago | Thu, Sep 17 | Normal Airline
        Find more flights
        Find more flights

Flight.News
Flights from Portland to Chicago operate an average of 29 times per day over the past 7 days, with a 76.8% on-time departure rate and a 98.3% on-time arrival rate.

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

The most popular airlines flying from Portland to Chicago are American Airlines, United Airlines, and Alaska Airlines, among 3 carriers on this route. Frontier Airlines offers the lowest fares. Based on Trip.com's flight booking data from the previous 12 months.
American Airlines logo American Airlines
United Airlines logo United Airlines
Alaska Airlines logo Alaska Airlines
Airlines are determined based on actual purchased flight tickets from Portland to Chicago according to previous 12 months data from Trip.com.

Trip.com price insights on flights from Portland to Chicago

Which month has the cheapest one-way flights from Portland to Chicago?

The average price of one-way flights from Portland to Chicago purchased by Trip.com users by month over the past 12 months.

Based on Trip.com’s data, the cheapest month for flights from Portland to Chicago is January, with an average price of $129; while the month with the highest flight price is usually November, with an average price of up to $303.

$303
$216
$129
$42
    Cheapest
  • $131
    Sep
  • $261
    Oct
  • $303
    Nov
  • $169
    Dec
  • $129
    Jan
  • $237
    Feb
  • $201
    Mar
  • $250
    Apr
  • $263
    May
  • $235
    Jun
  • $212
    Jul
  • $265
    Aug

When is the cheapest day to fly from Portland to Chicago during Columbus Day?

Data is based on the lowest one-way price from Portland to Chicago during Columbus Day on Trip.com in the past 3 days.

Columbus Day is scheduled for Oct 12. The cheapest flights from Portland to Chicago are available on Oct 13, with fares starting at $171.

$200
$186
$171
$157
    Cheapest
  • $200
    9
    Oct
  • $195
    10
  • $181
    11
  • $175
    12
  • $171
    13
  • $177
    14

Frequently Asked Questions

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

    Based on Trip.com data, Frontier Airlines offers one-way fares as low as $99 on Cheapest nonstop routes (e.g. PDX to ORD on Thu, Sep 17), while Delta Air Lines offers Cheapest nonstop round-trips from $248 departing on Tue, Oct 13 and returning on Wed, Oct 14.
  • At the moment, you can catch a nonstop flight from Portland to Chicago with the following airlines, including: American Airlines United Airlines Alaska 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 4 hours 42 minutes to fly from Portland (PDX) to Chicago (CHI).
  • By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Portland to Chicago 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 59 flight per week flying from Portland to Chicago. You can check the weekly schedule for popular airlines on this route below: American Airlines: S/M/T/W/T/F/S -- AA3329 (06:07)
  • To find best deals on flights from Portland to Chicago, 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 Thu, Sep 17, with one-way flights priced at just $99.
    · 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 Chicago travel is around July.
    · Get exclusive promo codes for Trip.com app users.
  • The cheapest months to fly from Portland to Chicago is October, when demand for travel is lower.
  • You can arrive at any of the following airports in Chicago: O'Hare International Airport (ORD), Chicago Midway International Airport (MDW), and Chicago Rockford International Airport (RFD). Flights from Portland International Airport to O'Hare International Airport (PDX-ORD) are by far the most popular option for this route.
  • The time difference between Chicago and Portland is 2h.
  • 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 Portland to Chicago is $214. 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 Portland to Chicago is $420. The final price depends on the outbound and return dates, airline and fare conditions.
  • Enter Portland and Chicago, 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.

Explore More Popular Flights

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.