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Portland International Airport to Chicago Midway International Airport flight

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

      • PDX 12:30 AM
        6h 16m
        1 stop
        MDW 8:46 AM
        Portland - Chicago | Wed, Apr 15 | Delta Air Lines
        ORD 6:00 PM
        7h 56m
        1 stop
        PDX 11:56 PM
        Chicago - Portland | Wed, Apr 15 | Delta Air Lines
        €163 €207
        21% off
        21% off
        €207 €163
      • PDX 11:15 PM
        7h 32m
        1 stop
        MDW 8:47 AM
        Portland - Chicago | Mon, Apr 13 | Delta Air Lines
        ORD 7:10 PM
        6h 43m
        1 stop
        PDX 11:53 PM
        Chicago - Portland | Tue, Apr 21 | Delta Air Lines
        €168 €207
        19% off
        19% off
        €207 €168
      • PDX 12:30 AM
        6h 16m
        1 stop
        MDW 8:46 AM
        Portland - Chicago | Wed, Apr 29 | Delta Air Lines
        ORD 5:04 PM
        6h 52m
        1 stop
        PDX 9:56 PM
        Chicago - Portland | Wed, May 6 | Delta Air Lines
        €173 €207
        16% off
        16% off
        €207 €173
      • PDX 11:12 PM
        7h 31m
        1 stop
        MDW 8:43 AM
        Portland - Chicago | Tue, Jun 2 | Delta Air Lines
        ORD 2:07 PM
        9h 43m
        1 stop
        PDX 9:50 PM
        Chicago - Portland | Tue, Jun 9 | Delta Air Lines
        €173
        16% off
        €207 €173
      • PDX 12:30 AM
        6h 36m
        1 stop
        MDW 9:06 AM
        Portland - Chicago | Sat, Apr 25 | Delta Air Lines
        ORD 12:46 PM
        6h 24m
        1 stop
        PDX 5:10 PM
        Chicago - Portland | Wed, Apr 29 | Delta Air Lines
        €178
        14% off
        €207 €178
      • PDX 12:30 AM
        6h 16m
        1 stop
        MDW 8:46 AM
        Portland - Chicago | Wed, May 6 | Delta Air Lines
        ORD 12:47 PM
        8h 39m
        1 stop
        PDX 7:26 PM
        Chicago - Portland | Wed, May 13 | Delta Air Lines
        €178
        14% off
        €207 €178
      • PDX 9:39 PM
        10h 21m
        1 stop
        MDW 10:00 AM
        Portland - Chicago | Tue, May 26 | Delta Air Lines
        ORD 2:00 PM
        10h 2m
        1 stop
        PDX 10:02 PM
        Chicago - Portland | Tue, Jun 2 | Delta Air Lines
        €178
        14% off
        €207 €178
      • PDX 12:30 AM
        6h 21m
        1 stop
        MDW 8:51 AM
        Portland - Chicago | Sun, Apr 26 | Delta Air Lines
        ORD 7:12 PM
        6h 41m
        1 stop
        PDX 11:53 PM
        Chicago - Portland | Wed, Apr 29 | Delta Air Lines
        €186
        10% off
        €207 €186
      • PDX 12:30 AM
        6h 16m
        1 stop
        MDW 8:46 AM
        Portland - Chicago | Thu, Apr 16 | Delta Air Lines
        ORD 7:15 AM
        9h 38m
        1 stop
        PDX 2:53 PM
        Chicago - Portland | Wed, Apr 22 | Delta Air Lines
        €188
        9% off
        €207 €188
      • PDX 1:00 PM
        17h 25m
        1 stop
        CHI Invalid Date
        Portland - Chicago | Tue, Apr 14 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        PDX 4:00 PM
        Chicago - Portland | Thu, Apr 16 | Normal Airline
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      • PDX 11:15 PM
        7h 32m
        1 stop
        MDW 8:47 AM
        Portland - Chicago | Wed, Apr 29 | Delta Air Lines
        €91 €126
        28% off
        28% off
        €126 €91
      • PDX 11:15 PM
        7h 32m
        1 stop
        MDW 8:47 AM
        Portland - Chicago | Tue, Apr 28 | Delta Air Lines
        €91 €126
        28% off
        28% off
        €126 €91
      • PDX 12:30 AM
        6h 21m
        1 stop
        MDW 8:51 AM
        Portland - Chicago | Wed, May 6 | Delta Air Lines
        €92 €126
        27% off
        27% off
        €126 €92
      • PDX 11:15 PM
        7h 32m
        1 stop
        MDW 8:47 AM
        Portland - Chicago | Sat, Apr 25 | Delta Air Lines
        €108
        14% off
        €126 €108
      • PDX 11:12 PM
        7h 31m
        1 stop
        MDW 8:43 AM
        Portland - Chicago | Mon, May 11 | Delta Air Lines
        €111
        12% off
        €126 €111
      • PDX 12:30 AM
        6h 16m
        1 stop
        MDW 8:46 AM
        Portland - Chicago | Wed, Apr 22 | Delta Air Lines
        €112
        11% off
        €126 €112
      • PDX 11:12 PM
        7h 31m
        1 stop
        MDW 8:43 AM
        Portland - Chicago | Tue, May 12 | Delta Air Lines
        €114
        10% off
        €126 €114
      • PDX 1:00 PM
        17h 25m
        1 stop
        CHI Invalid Date
        Portland - Chicago | Tue, Apr 14 | Normal Airline
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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.

Selected Airlines from Portland International Airport 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 €91

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Flight Schedule from Portland International Airport 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. DL472

    Portland International Airport

    12:30 AM

    PDX

    3h 10m

    Nonstop

    5:40 AM

    MSP

    S M T W T F S
    Search

  2. DL3795

    Minneapolis-Saint Paul International Airport

    7:00 AM

    MSP

    1h 46m

    Nonstop

    8:46 AM

    MDW

    S M T W T F S

  3. DL573

    Portland International Airport

    11:15 PM

    PDX

    4h 13m

    Nonstop

    6:28 AM

    DTW

    S M T W T F S
    Search

  4. DL5218

    Detroit Metropolitan Wayne County Airport

    8:25 AM

    DTW

    1h 22m

    Nonstop

    8:47 AM

    MDW

    S M T W T F S

  5. DL888

    Portland International Airport

    9:45 PM

    PDX

    4h 42m

    Nonstop

    5:27 AM

    ATL

    S M T W T F S
    Search

  6. DL1063

    Hartsfield-Jackson Atlanta International Airport

    8:55 AM

    ATL

    1h 57m

    Nonstop

    9:52 AM

    MDW

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

Flight distance2,814.5 km
Cheapest one-way ticket price€91
Cheapest return ticket price€163

FAQs for Portland International Airport to Chicago Midway International Airport Flights

  • How long is a flight from Portland International Airport to Chicago Midway International Airport?

    It takes around 3 hours 53 minutes to fly from Portland International Airport (pdx) to Chicago Midway International Airport (mdw).
  • There are around 2 daily flights from Portland International Airport (PDX) to Chicago Midway International Airport (MDW).
  • Tickets cost around €257 in May, making it the cheapest month to book. Portland International Airport (PDX) 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 Airport (PDX) to Chicago Midway International Airport (MDW) is quite popular. Without considering departure times or holidays, tickets cost around €467 in April, the most expensive month to book this route.
    • The distance from Chicago O'Hare International Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
    • The distance from Chicago Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.
  • The closest airport to Chicago Midway International Airport (MDW) is Chicago O'Hare International Airport. The distance is around 25 km.

Popular Destinations

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

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Prices displayed on this page are all-inclusive (incl. taxes, fuel surcharges, Civil Aviation Development Fund, etc.), and all fees are clearly shown before payment. Charges for checked baggage, onboard meals, Wi-Fi, and other optional services may also appear in the flight cards where applicable.

Real-time pricing updates

Prices, availability, and travel information on this page have been updated within the last 24 hours, and for many routes the data may refresh in real time. The more popular the route, the more accurate and up-to-date the data.

Change & Cancellation Policy

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Voluntary cancellation/change:
To request a change or cancellation, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and flight segment, and submit your request. Please note that additional charges may apply based on the airline’s fare rules.
Cancellation/change due to a flight schedule change:
If your flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For full details of change and cancellation policies, please refer to the customer support pages.