Trip.com
>
Cheap Flights
>
United States
>
Illinois
>
Chicago
>
Flights from Portland to Chicago

Airlines operating flights from Portland to Chicago

Choose from 1 airlines flying from Portland to Chicago, including United Airlines, and . United Airlines currently offers the cheapest ticket on this route.
United Airlines logo United Airlines

Find the cheapest direct flight options from Portland to Chicago over the next three months. Book one-way tickets from VND 3,974,104 and round-trip tickets from VND 6,981,735.

      • Cheapest nonstop
        PWM 16:10
        3h 8m
        Direct
        ORD 18:18
        Portland - Chicago | Wed, Jan 14 | United Airlines
        ORD 11:00
        2h 39m
        Direct
        PWM 14:39
        Chicago - Portland | Wed, Jan 21 | United Airlines
        VND 6,981,735 VND 8,041,705
        13% OFF
        13% OFF
        VND 8,041,705 VND 6,981,735
      • PWM 16:10
        3h 8m
        Direct
        ORD 18:18
        Portland - Chicago | Fri, Jan 23 | United Airlines
        ORD 11:00
        2h 39m
        Direct
        PWM 14:39
        Chicago - Portland | Sun, Jan 25 | United Airlines
        VND 7,157,117 VND 8,041,705
        11% OFF
        11% OFF
        VND 8,041,705 VND 7,157,117
      • PWM 05:30
        6h 30m
        1 stop
        ORD 11:00
        Portland - Chicago | Sun, Jan 11 | Delta Air Lines
        ORD 18:25
        4h 55m
        1 stop
        PWM 00:20
        Chicago - Portland | Sun, Jan 18 | Delta Air Lines
        VND 5,686,886 VND 8,041,705
        28% OFF
        28% OFF
        VND 8,041,705 VND 5,686,886
      • PWM 17:57
        5h 37m
        1 stop
        ORD 22:34
        Portland - Chicago | Mon, Jan 12 | Delta Air Lines
        ORD 18:25
        4h 55m
        1 stop
        PWM 00:20
        Chicago - Portland | Mon, Jan 19 | Delta Air Lines
        VND 5,686,886
        28% OFF
        VND 8,041,705 VND 5,686,886
      • PWM 05:30
        6h 29m
        1 stop
        ORD 10:59
        Portland - Chicago | Wed, Jan 14 | Delta Air Lines
        ORD 14:50
        6h 37m
        1 stop
        PWM 22:27
        Chicago - Portland | Wed, Jan 21 | Delta Air Lines
        VND 5,686,886
        28% OFF
        VND 8,041,705 VND 5,686,886
      • PWM 05:30
        7h 31m
        1 stop
        MDW 12:01
        Portland - Chicago | Wed, Jan 28 | Delta Air Lines
        ORD 14:49
        6h 40m
        1 stop
        PWM 22:29
        Chicago - Portland | Wed, Feb 4 | Delta Air Lines
        VND 5,709,275
        28% OFF
        VND 8,041,705 VND 5,709,275
      • PWM 06:00
        8h 26m
        1 stop
        ORD 13:26
        Portland - Chicago | Thu, Jan 29 | Delta Air Lines
        ORD 14:49
        6h 40m
        1 stop
        PWM 22:29
        Chicago - Portland | Wed, Feb 4 | Delta Air Lines
        VND 5,709,275
        28% OFF
        VND 8,041,705 VND 5,709,275
      • PWM 05:30
        9h 9m
        1 stop
        ORD 13:39
        Portland - Chicago | Fri, Jan 30 | Delta Air Lines
        ORD 14:49
        6h 40m
        1 stop
        PWM 22:29
        Chicago - Portland | Wed, Feb 4 | Delta Air Lines
        VND 5,709,275
        28% OFF
        VND 8,041,705 VND 5,709,275
      • PWM 14:35
        7h 18m
        1 stop
        ORD 20:53
        Portland - Chicago | Sat, Jan 17 | Delta Air Lines
        ORD 18:25
        4h 55m
        1 stop
        PWM 00:20
        Chicago - Portland | Mon, Jan 19 | Delta Air Lines
        VND 5,713,007
        28% OFF
        VND 8,041,705 VND 5,713,007
      • PWM 06:08
        6h 55m
        1 stop
        ORD 12:03
        Portland - Chicago | Wed, Dec 10 | Delta Air Lines
        ORD 06:45
        4h 28m
        1 stop
        PWM 12:13
        Chicago - Portland | Mon, Dec 15 | Delta Air Lines
        VND 5,720,470
        28% OFF
        VND 8,041,705 VND 5,720,470
      • PWM 05:30
        6h 29m
        1 stop
        ORD 10:59
        Portland - Chicago | Wed, Jan 7 | Delta Air Lines
        ORD 06:50
        4h 21m
        1 stop
        PWM 12:11
        Chicago - Portland | Sat, Jan 10 | Delta Air Lines
        VND 5,720,470
        28% OFF
        VND 8,041,705 VND 5,720,470
      • PWM 05:30
        9h 19m
        1 stop
        ORD 13:49
        Portland - Chicago | Sat, Jan 31 | Delta Air Lines
        ORD 14:49
        6h 40m
        1 stop
        PWM 22:29
        Chicago - Portland | Tue, Feb 3 | Delta Air Lines
        VND 5,724,201
        28% OFF
        VND 8,041,705 VND 5,724,201
      • PWM 13:00
        17h 25m
        1 stop
        CHI Invalid Date
        Portland - Chicago | Fri, Dec 12 | Normal Airline
        CHI 15:00
        6h
        Direct
        PWM 16:00
        Chicago - Portland | Sun, Dec 14 | Normal Airline
        Find More Flights
        Find More Flights
      • Cheapest nonstop
        PWM 16:10
        3h 8m
        Direct
        ORD 18:18
        Portland - Chicago | Sat, Jan 31 | United Airlines
        VND 3,974,104 VND 4,473,670
        11% OFF
        11% OFF
        VND 4,473,670 VND 3,974,104
      • PWM 16:10
        3h 8m
        Direct
        ORD 18:18
        Portland - Chicago | Wed, Jan 14 | United Airlines
        VND 3,981,567 VND 4,473,670
        11% OFF
        11% OFF
        VND 4,473,670 VND 3,981,567
      • PWM 12:10
        6h 45m
        1 stop
        MDW 17:55
        Portland - Chicago | Tue, Feb 3 | Delta Air Lines
        VND 2,858,369 VND 4,473,670
        36% OFF
        36% OFF
        VND 4,473,670 VND 2,858,369
      • PWM 05:30
        9h 10m
        1 stop
        ORD 13:40
        Portland - Chicago | Sun, Jan 18 | Delta Air Lines
        VND 2,877,027
        36% OFF
        VND 4,473,670 VND 2,877,027
      • PWM 12:48
        4h 50m
        1 stop
        ORD 16:38
        Portland - Chicago | Sat, Jan 24 | Delta Air Lines
        VND 2,884,490
        36% OFF
        VND 4,473,670 VND 2,884,490
      • PWM 06:08
        7h 2m
        1 stop
        ORD 12:10
        Portland - Chicago | Tue, Dec 16 | Delta Air Lines
        VND 2,888,222
        35% OFF
        VND 4,473,670 VND 2,888,222
      • PWM 06:08
        6h 55m
        1 stop
        ORD 12:03
        Portland - Chicago | Wed, Dec 17 | Delta Air Lines
        VND 2,888,222
        35% OFF
        VND 4,473,670 VND 2,888,222
      • PWM 05:30
        6h 4m
        1 stop
        MDW 10:34
        Portland - Chicago | Sat, Jan 10 | Delta Air Lines
        VND 2,888,222
        35% OFF
        VND 4,473,670 VND 2,888,222
      • PWM 12:48
        4h 52m
        1 stop
        ORD 16:40
        Portland - Chicago | Sat, Jan 31 | Delta Air Lines
        VND 2,888,222
        35% OFF
        VND 4,473,670 VND 2,888,222
      • PWM 17:56
        5h 38m
        1 stop
        ORD 22:34
        Portland - Chicago | Mon, Jan 5 | Delta Air Lines
        VND 2,891,953
        35% OFF
        VND 4,473,670 VND 2,891,953
      • PWM 14:35
        7h 18m
        1 stop
        ORD 20:53
        Portland - Chicago | Sat, Jan 17 | Delta Air Lines
        VND 2,918,074
        35% OFF
        VND 4,473,670 VND 2,918,074
      • PWM 05:30
        6h 29m
        1 stop
        ORD 10:59
        Portland - Chicago | Wed, Jan 14 | Delta Air Lines
        VND 2,929,269
        35% OFF
        VND 4,473,670 VND 2,929,269
      • PWM 13:00
        17h 25m
        1 stop
        CHI Invalid Date
        Portland - Chicago | Fri, Dec 12 | Normal Airline
        Find More Flights
        Find More Flights

Displayed flight fares from Portland to Chicago are based on average prices across airlines for the next 3 months, according to the latest Trip.com database.

Flight details for Portland to Chicago

The distance between Portland and Chicago is 1,425.81 km. It takes around 3 hours 47 minutes on average to fly from Portland to Chicago. Based on Trip.com's data, travel demand peaks in July. The off-season for travel is September.

Cheapest one-way flight priceVND 2,858,369
Cheapest round-trip ticket priceVND 5,686,886
Off-season for travelSeptember
Peak season for travelJuly
Flight distance1,425.81 km
Average flight time3 hours 47 minutes
Popular airlineUnited Airlines

Find the best time to fly from Portland to Chicago

The cheapest time for Portland to Chicago flights: Feb 1 to Feb 8 — one way flight prices from VND 2,858,369.

Cheapest flights
From price
Search
  • 714
  • 1421
  • 2128

  • Jan

    284
  • 411
  • 1118
  • 1825

  • Feb

    251
  • 18
  • 815
  • 1522

  • Mar

    221
Displayed fare trends are based on Trip.com's aggregated average of the lowest flight prices from Portland to Chicago, calculated over the upcoming 10 weeks.

Flight FAQs

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

    Based on Trip.com data, Delta Air Lines offers one-way fares as low as VND 2,858,369 on Cheapest nonstop routes (e.g. PWM to MDW on Tue, Feb 3), while Delta Air Lines offers Cheapest nonstop round-trips from VND 5,686,886 departing on Sun, Jan 11 and returning on Sun, Jan 18.
  • At the moment, you can catch a nonstop flight from Portland to Chicago 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 3 hours 47 minutes to fly from Portland (PWM) 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 20 flight per week flying from Portland to Chicago. You can check the weekly schedule for popular airlines on this route below: United Airlines: S/M/T/W/T/F/S -- UA3695 (10:05) United Airlines: S/M/T/W/T/F/S -- UA1525 (06:20)
  • 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 Tue, Feb 3, with one-way flights priced at just VND 2,858,369.
    · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is United 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 September, when demand for travel is lower.
  • After crunching the numbers on our December flight calendar, it's currently cheapest to fly from Portland to Chicago on December 10, 2025 with Delta Air Lines, with prices starting at VND 5,720,469.
  • You can land at any one of the following hubs in Chicago, with Portland International Jetport to O'Hare International Airport (PWM-ORD) is by far the most common option on this route: O'Hare International Airport (ORD) Midway International Airport (MDW) Chicago Rockford International Airport (RFD).
  • The time difference between Chicago and Portland 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.