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Portland to Midway International Airport flight
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Cheap Flights from Portland to Midway International Airport

  • One way
  • Round-trip
      • Cheapest nonstop
        PDX6:20 AM
        3h 55m
        Nonstop
        MDW12:15 PM
        Portland - Chicago|Sat, Jul 5|Southwest Airlines
        PHP 5,089PHP 18,648
        73% OFF
        73% OFF
        PHP 18,648PHP 5,089

        Choose Southwest Airlines flights from Portland to Chicago. The one-way direct flight with Southwest Airlines departs from Portland International Airport on Sat, Jul 5, arriving at Midway International Airport. One-way Prices start from PHP 5,089 including taxes and charges.

      • PDX5:50 AM
        3h 55m
        Nonstop
        MDW11:45 AM
        Portland - Chicago|Mon, Jun 30|Southwest Airlines
        PHP 15,478PHP 18,648
        17% OFF
        17% OFF
        PHP 18,648PHP 15,478

        Choose Southwest Airlines flights from Portland to Chicago. The one-way direct flight with Southwest Airlines departs from Portland International Airport on Mon, Jun 30, arriving at Midway International Airport. One-way Prices start from PHP 15,478 including taxes and charges.

      • PDX11:11 PM
        7h 33m
        1 stop
        MDW8:44 AM
        Portland - Chicago|Tue, Jul 8|Delta Air Lines
        PHP 4,281PHP 18,648
        77% OFF
        77% OFF
        PHP 18,648PHP 4,281

        Choose Delta Air Lines flights from Portland to Chicago. The one-way connecting flight with Delta Air Lines departs from Portland International Airport on Tue, Jul 8, arriving at Midway International Airport. One-way Prices start from PHP 4,281 including taxes and charges.

      • PDX12:40 AM
        6h 5m
        1 stop
        MDW8:45 AM
        Portland - Chicago|Wed, Jul 23|Delta Air Lines
        PHP 4,553
        PHP 4,553

        Choose Delta Air Lines flights from Portland to Chicago. The one-way connecting flight with Delta Air Lines departs from Portland International Airport on Wed, Jul 23, arriving at Midway International Airport. One-way Prices start from PHP 4,553 including taxes and charges.

      • PDX12:40 AM
        6h 5m
        1 stop
        MDW8:45 AM
        Portland - Chicago|Wed, Jul 9|Delta Air Lines
        PHP 4,561
        PHP 4,561

        Choose Delta Air Lines flights from Portland to Chicago. The one-way connecting flight with Delta Air Lines departs from Portland International Airport on Wed, Jul 9, arriving at Midway International Airport. One-way Prices start from PHP 4,561 including taxes and charges.

      • PDX12:40 AM
        6h 5m
        1 stop
        MDW8:45 AM
        Portland - Chicago|Tue, Jul 15|Delta Air Lines
        PHP 4,693
        PHP 4,693

        Choose Delta Air Lines flights from Portland to Chicago. The one-way connecting flight with Delta Air Lines departs from Portland International Airport on Tue, Jul 15, arriving at Midway International Airport. One-way Prices start from PHP 4,693 including taxes and charges.

      • PDX12:40 AM
        6h 5m
        1 stop
        MDW8:45 AM
        Portland - Chicago|Wed, Aug 6|Delta Air Lines
        PHP 4,693
        PHP 4,693

        Choose Delta Air Lines flights from Portland to Chicago. The one-way connecting flight with Delta Air Lines departs from Portland International Airport on Wed, Aug 6, arriving at Midway International Airport. One-way Prices start from PHP 4,693 including taxes and charges.

      • PDX12:46 AM
        6h 4m
        1 stop
        MDW8:50 AM
        Portland - Chicago|Sat, Aug 16|Delta Air Lines
        PHP 4,716
        PHP 4,716

        Choose Delta Air Lines flights from Portland to Chicago. The one-way connecting flight with Delta Air Lines departs from Portland International Airport on Sat, Aug 16, arriving at Midway International Airport. One-way Prices start from PHP 4,716 including taxes and charges.

      • PDX12:40 AM
        6h 5m
        1 stop
        MDW8:45 AM
        Portland - Chicago|Sat, Jul 12|Delta Air Lines
        PHP 4,810
        PHP 4,810

        Choose Delta Air Lines flights from Portland to Chicago. The one-way connecting flight with Delta Air Lines departs from Portland International Airport on Sat, Jul 12, arriving at Midway International Airport. One-way Prices start from PHP 4,810 including taxes and charges.

      • PDX11:00 PM
        7h 35m
        1 stop
        MDW8:35 AM
        Portland - Chicago|Sat, Aug 30|Delta Air Lines
        PHP 4,810
        PHP 4,810

        Choose Delta Air Lines flights from Portland to Chicago. The one-way connecting flight with Delta Air Lines departs from Portland International Airport on Sat, Aug 30, arriving at Midway International Airport. One-way Prices start from PHP 4,810 including taxes and charges.

      • PDX1:00 PM
        3h 5m
        Nonstop
        MDW2:00 PM
        Portland - Chicago|Thu, Jun 19|Southwest Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

There are 1 airport(s) in Portland. Discover the top routes now!

  • 0.36 km from downtown Portland
    Portland International Airport
    Tickets From
    PHP 4,281

Flight Schedule from Portland to Midway International Airport

Flight info.
Departure
Arrival
Weekly Schedule

  1. DL2359

    Delta Air Lines

    00:40

    PDX

    3.3h

    05:55

    MSP

    SMTWTFS
    Search

  2. DL3795

    Delta Air Lines

    07:00

    MSP

    1.6h

    08:38

    MDW

    SMTWTFS

  3. DL2359

    Delta Air Lines

    00:40

    PDX

    3.3h

    05:55

    MSP

    SMTWTFS
    Search

  4. DL3543

    Delta Air Lines

    07:13

    MSP

    1.6h

    08:50

    MDW

    SMTWTFS

  5. WN2735

    Southwest Airlines

    05:50

    PDX

    3.9h

    Nonstop

    11:45

    MDW

    SMTWTF-
    Search

  6. F91790

    Frontier Airlines

    06:35

    PDX

    2.6h

    10:12

    DEN

    SMTWTFS
    Search

  7. WN2618

    Southwest Airlines

    17:05

    DEN

    2.3h

    20:25

    MDW

    SMTWTFS

  8. DL539

    Delta Air Lines

    12:12

    PDX

    4.9h

    20:07

    ATL

    SMTWTFS
    Search

  9. DL1076

    Delta Air Lines

    20:50

    ATL

    1.9h

    21:45

    MDW

    SMTWTFS

  10. WN4170

    Southwest Airlines

    13:55

    PDX

    3.9h

    Nonstop

    19:50

    MDW

    SMTWTFS
    Search

  11. F91106

    Frontier Airlines

    18:16

    PDX

    2.4h

    20:39

    LAS

    ------S
    Search

  12. F92330

    Frontier Airlines

    09:19

    LAS

    3.6h

    14:56

    MDW

    S---T-S

  13. F92554

    Frontier Airlines

    18:53

    PDX

    2.7h

    22:37

    DEN

    SM-WTFS
    Search

  14. F92210

    Frontier Airlines

    17:26

    DEN

    2.5h

    20:54

    MDW

    S--WTFS

  15. DL888

    Delta Air Lines

    21:45

    PDX

    4.8h

    05:35

    ATL

    SMTWT-S
    Search

  16. DL1063

    Delta Air Lines

    08:55

    ATL

    1.9h

    09:51

    MDW

    SMTWTFS

  17. DL704

    Delta Air Lines

    23:10

    PDX

    4.2h

    06:19

    DTW

    SMTWTFS
    Search

  18. DL3858

    Delta Air Lines

    08:25

    DTW

    1.3h

    08:42

    MDW

    SMTWTFS
Find more flights and airlines

Flight Info of Flights from Portland to Midway International Airport

Cheapest round-trip ticket pricePHP 7,148
Cheapest one-way flight pricePHP 4,281
Off-season for travelApril
Peak season for travelMarch

FAQs for Portland to Midway International Airport Flights

  • When are flight tickets from Portland (PDX) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Portland to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Portland (PDX) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around PHP 19,720.

  • How long does it take to fly from Portland (PDX) to Chicago (CHI) and what is the distance?

    It takes around 3 hours 59 minutes to fly from Portland (PDX) to Chicago (CHI).

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.

  • What are the most popular airlines that fly from Portland (PDX) to Chicago (CHI)?

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