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Portland International Jetport to Chicago Midway International Airport flight

Search for flights from Portland to Chicago and check out affordable one-way and round-trip options.

      • PWM 12:50
        6h 43m
        1 stop
        MDW 18:33
        Portland - Chicago | Sat, May 23 | Delta Air Lines
        ORD 20:54
        2h 41m
        Direct
        PWM 00:35
        Chicago - Portland | Mon, May 25 | American Airlines
        CAD 359 CAD 526
        32% off
        32% off
        CAD 526 CAD 359
      • PWM 12:40
        6h 51m
        1 stop
        MDW 18:31
        Portland - Chicago | Thu, Jun 11 | Delta Air Lines
        ORD 13:46
        8h 29m
        1 stop
        PWM 23:15
        Chicago - Portland | Mon, Jun 15 | Delta Air Lines
        CAD 384 CAD 526
        27% off
        27% off
        CAD 526 CAD 384
      • PWM 11:48
        7h 30m
        1 stop
        MDW 18:18
        Portland - Chicago | Sun, Jun 14 | Delta Air Lines
        ORD 13:46
        8h 29m
        1 stop
        PWM 23:15
        Chicago - Portland | Mon, Jun 15 | Delta Air Lines
        CAD 384 CAD 526
        27% off
        27% off
        CAD 526 CAD 384
      • PWM 12:55
        6h 38m
        1 stop
        MDW 18:33
        Portland - Chicago | Fri, May 22 | Delta Air Lines
        ORD 07:00
        4h
        1 stop
        PWM 12:00
        Chicago - Portland | Tue, May 26 | Delta Air Lines
        CAD 393
        25% off
        CAD 526 CAD 393
      • PWM 12:50
        6h 43m
        1 stop
        MDW 18:33
        Portland - Chicago | Mon, Jun 1 | Delta Air Lines
        ORD 10:35
        5h 14m
        1 stop
        PWM 16:49
        Chicago - Portland | Tue, Jun 9 | Delta Air Lines
        CAD 397
        25% off
        CAD 526 CAD 397
      • PWM 14:05
        8h 4m
        1 stop
        MDW 21:09
        Portland - Chicago | Wed, May 27 | Delta Air Lines
        ORD 18:31
        5h 12m
        1 stop
        PWM 00:43
        Chicago - Portland | Fri, May 29 | Delta Air Lines
        CAD 408
        22% off
        CAD 526 CAD 408
      • PWM 14:05
        8h 4m
        1 stop
        MDW 21:09
        Portland - Chicago | Sun, May 24 | Delta Air Lines
        ORD 07:05
        4h 33m
        1 stop
        PWM 12:38
        Chicago - Portland | Wed, May 27 | Delta Air Lines
        CAD 418
        21% off
        CAD 526 CAD 418
      • PWM 12:55
        6h 38m
        1 stop
        MDW 18:33
        Portland - Chicago | Wed, Jun 3 | Delta Air Lines
        ORD 15:00
        7h 9m
        1 stop
        PWM 23:09
        Chicago - Portland | Sat, Jun 6 | Delta Air Lines
        CAD 426
        19% off
        CAD 526 CAD 426
      • PWM 12:50
        6h 43m
        1 stop
        MDW 18:33
        Portland - Chicago | Thu, May 21 | Delta Air Lines
        ORD 07:00
        3h 55m
        1 stop
        PWM 11:55
        Chicago - Portland | Sun, May 24 | Delta Air Lines
        CAD 431
        18% off
        CAD 526 CAD 431
      • PWM 13:00
        17h 25m
        1 stop
        CHI 14:00
        Portland - Chicago | Fri, May 22 | Normal Airline
        CHI 15:00
        6h
        Direct
        PWM 16:00
        Chicago - Portland | Sun, May 24 | Normal Airline
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      • PWM 12:55
        6h 38m
        1 stop
        MDW 18:33
        Portland - Chicago | Wed, Jun 3 | Delta Air Lines
        CAD 135 CAD 258
        48% off
        48% off
        CAD 258 CAD 135
      • PWM 11:48
        7h 30m
        1 stop
        MDW 18:18
        Portland - Chicago | Tue, Jun 30 | Delta Air Lines
        CAD 195 CAD 258
        24% off
        24% off
        CAD 258 CAD 195
      • PWM 12:50
        6h 43m
        1 stop
        MDW 18:33
        Portland - Chicago | Thu, May 28 | Delta Air Lines
        CAD 199 CAD 258
        23% off
        23% off
        CAD 258 CAD 199
      • PWM 06:00
        6h 56m
        1 stop
        MDW 11:56
        Portland - Chicago | Tue, May 26 | Delta Air Lines
        CAD 199
        23% off
        CAD 258 CAD 199
      • PWM 11:48
        7h 30m
        1 stop
        MDW 18:18
        Portland - Chicago | Mon, Jun 15 | Delta Air Lines
        CAD 200
        22% off
        CAD 258 CAD 200
      • PWM 06:00
        6h 56m
        1 stop
        MDW 11:56
        Portland - Chicago | Wed, May 27 | Delta Air Lines
        CAD 206
        20% off
        CAD 258 CAD 206
      • PWM 14:05
        8h 4m
        1 stop
        MDW 21:09
        Portland - Chicago | Fri, May 29 | Delta Air Lines
        CAD 209
        19% off
        CAD 258 CAD 209
      • PWM 11:48
        7h 30m
        1 stop
        MDW 18:18
        Portland - Chicago | Wed, Jul 1 | Delta Air Lines
        CAD 211
        18% off
        CAD 258 CAD 211
      • PWM 13:00
        17h 25m
        1 stop
        CHI 14:00
        Portland - Chicago | Fri, May 22 | Normal Airline
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        Find more flights

Flight fares from Portland International Jetport to Chicago Midway International Airport are based on average airline prices for the next 3 months, according to Trip.com’s latest data.

Selected Airlines from Portland International Jetport to Chicago Midway International Airport

See which airlines fly from Portland to Chicago. Find the airline that best meets your travel needs by comparing prices and treat yourself to an enjoyable journey.

Delta Air Lines
From CAD 135
American Airlines
From CAD 266

Find more flights and airlines

Flight Schedule from Portland International Jetport to Chicago Midway International Airport

Check the schedule for flights from Portland to Chicago and find the flight that best matches your travel plans.

Flight info.
Departure
Arrival
Weekly Schedule

  1. DL426

    Portland International Jetport

    12:50

    PWM

    2h 19m

    Direct

    15:09

    DTW

    S M T W T F S
    Search

  2. DL4677

    Detroit Metropolitan Wayne County Airport

    18:15

    DTW

    1h 22m

    Direct

    18:37

    MDW

    S M T W T F S

  3. DL1515

    Portland International Jetport

    06:00

    PWM

    3h 15m

    Direct

    09:15

    ATL

    S M T W T F S
    Search

  4. DL2417

    Hartsfield-Jackson Atlanta International Airport

    11:00

    ATL

    1h 56m

    Direct

    11:56

    MDW

    S M T W T - -

  5. DL2479

    Portland International Jetport

    14:14

    PWM

    2h 51m

    Direct

    17:05

    ATL

    S M T W T F S
    Search

  6. DL1076

    Hartsfield-Jackson Atlanta International Airport

    19:00

    ATL

    2h 2m

    Direct

    20:02

    MDW

    S M T W T F S
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Portland International Jetport to Chicago Midway International Airport Flights Info

Flight distance1,437.8km
Cheapest one-way ticket priceCAD 135
Cheapest return ticket priceCAD 359

FAQs for Portland International Jetport to Chicago Midway International Airport Flights

  • How long does it take to fly from Portland International Jetport (PWM) to Chicago Midway International Airport (MDW)?

    It takes around 2 hours 40 minutes to fly from Portland International Jetport (pwm) to Chicago Midway International Airport(mdw).
  • There are around 1 daily flights from Portland International Jetport (PWM) to Chicago Midway International Airport (MDW).
  • Tickets cost around CAD 250 in July, making it the cheapest month to book. Portland International Jetport (PWM) to Chicago Midway International Airport (MDW) is a popular route, so don't forget to book your tickets in advance.
  • The route from Portland International Jetport (PWM) to Chicago Midway International Airport (MDW) is quite popular. Without considering departure times or holidays, tickets cost around CAD 542 in June, the most expensive month to book this route.
    • The distance from Chicago O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Chicago Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
  • The closest airport to Chicago Midway International Airport (MDW) is Chicago O'Hare International Airport. The distance is around 25km.

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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.

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Prices displayed on 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, Wi-Fi, 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 the last 24 hours—even in real-time. The more popular the route, the more precise the data.

Change & Cancellation Policy

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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.