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Midway International Airport to Portland International Airport flight
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Cheap Flight Deals from Midway International Airport to Portland International Airport

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

  • One way
  • Round-trip
sortSort: Price (Lowest)
  • Sort: Price (Lowest)
  • Sort: Departure (Earliest)
      • MDW09:51
        9h 14m
        1 stop
        PDX17:05
        Chicago - Portland|Tue, May 7|Frontier Airlines
        CAD 84CAD 156
        46% OFF
        46% OFF
        CAD 156CAD 84
      • MDW05:30
        20h 29m
        1 stop
        PDX23:59
        Chicago - Portland|Tue, Apr 30|Frontier Airlines
        CAD 87CAD 156
        44% OFF
        44% OFF
        CAD 156CAD 87
      • MDW21:10
        17h 11m
        1 stop
        PDX12:21
        Chicago - Portland|Mon, May 20|Frontier Airlines
        CAD 90CAD 156
        42% OFF
        42% OFF
        CAD 156CAD 90
      • MDW05:01
        27h 47m
        1 stop
        PDX06:48
        Chicago - Portland|Wed, May 22|Frontier Airlines
        CAD 92
        CAD 92
      • MDW05:01
        14h 13m
        1 stop
        PDX17:14
        Chicago - Portland|Thu, May 9|Frontier Airlines
        CAD 92
        CAD 92
      • MDW07:35
        11h 7m
        1 stop
        PDX16:42
        Chicago - Portland|Thu, May 16|Frontier Airlines
        CAD 93
        CAD 93
      • MDW05:30
        27h 46m
        1 stop
        PDX07:16
        Chicago - Portland|Wed, May 1|Frontier Airlines
        CAD 94
        CAD 94
      • MDW21:10
        24h 10m
        1 stop
        PDX19:20
        Chicago - Portland|Tue, May 21|Frontier Airlines
        CAD 96
        CAD 96
      • MDW05:30
        20h 29m
        1 stop
        PDX23:59
        Chicago - Portland|Mon, May 6|Frontier Airlines
        CAD 99
        CAD 99
      • MDW05:30
        17h 40m
        2 stops
        PDX21:10
        Chicago - Portland|Tue, May 14|Frontier Airlines
        CAD 102
        CAD 102
      • MDW13:00
        3h 5m
        Direct
        PDX14:00
        Chicago - Portland|Sun, May 5|Frontier Airlines
        Find More Flights
        Find More Flights

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

Selected Airlines from Midway International Airport to Portland International Airport

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

Frontier Airlines
From CAD 84
Delta Air Lines
From CAD 141
Southwest Airlines
From CAD 260
ANA airlines
Find more flights and airlines

Find Cheaper Flights from Chicago to Portland. Enjoy direct flights with 1 airline

Explore other flights from Chicago to Portland to find the best alternative options.

  • Cheapest
    Spirit Airlines
    ORD
    20:00
    4h 30m
    Direct
    PDX
    22:30
    O'Hare International Airport - Portland International Airport
    Wed, May 8Spirit Airlines
    CAD 45
  • Spirit Airlines
    ORD
    20:00
    4h 30m
    Direct
    PDX
    22:30
    O'Hare International Airport - Portland International Airport
    Wed, May 8Spirit Airlines
    CAD 45
    Find More Flights
Flight Schedule from Midway International Airport to Portland International Airport

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

Flight info.
Departure
Arrival
Weekly Schedule

  1. F92209

    Frontier Airlines

    05:10

    MDW

    2.7h

    06:53

    DEN

    SMTWTFS
    Search

  2. F92687

    Frontier Airlines

    21:55

    DEN

    2.8h

    23:40

    PDX

    SMTWTFS

  3. F92209

    Frontier Airlines

    05:10

    MDW

    2.7h

    06:53

    DEN

    SMTWTFS
    Search

  4. F92105

    Frontier Airlines

    16:20

    DEN

    2.0h

    17:18

    PHX

    -M-WTFS

  5. F94031

    Frontier Airlines

    18:16

    PHX

    3.0h

    21:16

    PDX

    SMTWTFS

  6. DL1063

    Delta Air Lines

    10:00

    MDW

    1.9h

    12:53

    ATL

    SMTWTFS
    Search

  7. DL503

    Delta Air Lines

    16:59

    ATL

    5.3h

    19:15

    PDX

    SMTWTFS

  8. F94297

    Frontier Airlines

    12:31

    MDW

    2.7h

    15:15

    DFW

    SMTW-F-
    Search

  9. F93253

    Frontier Airlines

    16:33

    DFW

    4.2h

    18:47

    PDX

    -M-W-FS

  10. F92999

    Frontier Airlines

    16:00

    MDW

    2.5h

    18:30

    DFW

    SMTWTFS
    Search

  11. F93253

    Frontier Airlines

    16:33

    DFW

    4.2h

    18:47

    PDX

    -M-W-FS

  12. F94299

    Frontier Airlines

    19:30

    MDW

    2.9h

    22:23

    DFW

    ----T-S
    Search

  13. F93253

    Frontier Airlines

    16:33

    DFW

    4.2h

    18:47

    PDX

    -M-W-FS

  14. F92329

    Frontier Airlines

    22:00

    MDW

    4.0h

    23:59

    LAS

    SMTWTFS
    Search

  15. F91105

    Frontier Airlines

    06:50

    LAS

    2.4h

    09:15

    PDX

    S--WTFS

  16. F92945

    Frontier Airlines

    22:13

    MDW

    2.7h

    23:56

    DEN

    -M-W--S
    Search

  17. F92687

    Frontier Airlines

    21:55

    DEN

    2.8h

    23:40

    PDX

    SMTWTFS

  18. F92945

    Frontier Airlines

    22:13

    MDW

    2.7h

    23:56

    DEN

    -M-W--S
    Search

  19. F91789

    Frontier Airlines

    06:35

    DEN

    2.7h

    08:19

    PDX

    ---W--S

  20. F91591

    Frontier Airlines

    23:19

    MDW

    2.3h

    00:36

    DEN

    -----F-
    Search

  21. F91789

    Frontier Airlines

    06:35

    DEN

    2.7h

    08:19

    PDX

    ---W--S
Find more flights and airlines

Midway International Airport to Portland International Airport Flights Info

Flight distance2,814.5km
Cheapest one-way ticket priceCAD 83
Cheapest return ticket priceCAD 143

FAQs for Midway International Airport to Portland International Airport Flights

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

    It takes around 4 hours 25 minutes to fly from Midway International Airport (MDW) to Midway International Airport(PDX).

  • How many daily flights are there from Midway International Airport (MDW) to Portland International Airport (PDX)?

    There are around 1 daily flights from Midway International Airport (MDW) to Portland International Airport (PDX).

  • When are flight tickets from Midway International Airport (MDW) to Portland International Airport (PDX) the cheapest?

    Tickets cost around CAD 577 in May, making it the cheapest month to book. Midway International Airport (MDW) to Portland International Airport (PDX) is a popular route, so don't forget to book your tickets in advance.

  • When are flight tickets from Midway International Airport (MDW) to Portland International Airport (PDX) most expensive?

    The route from Midway International Airport (MDW) to Portland International Airport (PDX) is quite popular. Without considering departure times or holidays, tickets cost around CAD 577 in May, the most expensive month to book this route.

  • Which airline operates the most direct flights from Midway International Airport (MDW) to Portland International Airport (PDX)?

    Southwest Airlines is a very popular airline operating an average of 437 flights per month.

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