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Midway International Airport to Portland International Airport flight
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Cheap Flights 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 by: Lowest Price
  • Sort by: Lowest Price
  • Sort by: Earliest Flight
      • MDW09:51
        9h 14m
        1 stop
        PDX17:05
        Chicago - Portland|Tue, May 7|Frontier Airlines
        $62$97
        36% OFF
        36% OFF
        $97$62
      • MDW05:30
        20h 29m
        1 stop
        PDX23:59
        Chicago - Portland|Tue, Apr 30|Frontier Airlines
        $64$97
        34% OFF
        34% OFF
        $97$64
      • MDW21:10
        17h 11m
        1 stop
        PDX12:21
        Chicago - Portland|Mon, May 20|Frontier Airlines
        $66$97
        32% OFF
        32% OFF
        $97$66
      • MDW05:30
        27h 46m
        1 stop
        PDX07:16
        Chicago - Portland|Wed, May 8|Frontier Airlines
        $67
        $67
      • MDW05:01
        27h 47m
        1 stop
        PDX06:48
        Chicago - Portland|Wed, May 22|Frontier Airlines
        $67
        $67
      • MDW21:29
        18h 21m
        1 stop
        PDX13:50
        Chicago - Portland|Sat, May 4|Frontier Airlines
        $67
        $67
      • MDW05:01
        14h 13m
        1 stop
        PDX17:14
        Chicago - Portland|Thu, May 9|Frontier Airlines
        $68
        $68
      • MDW07:35
        11h 7m
        1 stop
        PDX16:42
        Chicago - Portland|Thu, May 16|Frontier Airlines
        $68
        $68
      • MDW05:30
        27h 46m
        1 stop
        PDX07:16
        Chicago - Portland|Wed, May 1|Frontier Airlines
        $69
        $69
      • MDW21:10
        24h 10m
        1 stop
        PDX19:20
        Chicago - Portland|Tue, May 21|Frontier Airlines
        $71
        $71
      • MDW13:00
        3h 5m
        Direct
        PDX14:00
        Chicago - Portland|Mon, May 6|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 $62
Delta Air Lines
From $104
Southwest Airlines
From $190
ANA airlines
Find more flights and airlines

Find Cheaper Flights from Chicago to Portland. Enjoy nonstop 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
    $32
  • Spirit Airlines
    ORD
    20:00
    4h 30m
    Direct
    PDX
    22:30
    O'Hare International Airport - Portland International Airport
    Wed, May 8Spirit Airlines
    $32
    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. DL1063

    Delta Air Lines

    10:00

    MDW

    1.9h

    12:53

    ATL

    SMTWTFS
    Search

  2. DL503

    Delta Air Lines

    16:45

    ATL

    5.1h

    18:51

    PDX

    SMTWTFS

  3. F92209

    Frontier Airlines

    10:02

    MDW

    2.8h

    11:49

    DEN

    SMTWTFS
    Search

  4. F92687

    Frontier Airlines

    21:55

    DEN

    2.8h

    23:40

    PDX

    SMTWTFS

  5. F92209

    Frontier Airlines

    10:02

    MDW

    2.8h

    11:49

    DEN

    SMTWTFS
    Search

  6. F92105

    Frontier Airlines

    16:20

    DEN

    2.0h

    17:18

    PHX

    -M-WTFS

  7. F94031

    Frontier Airlines

    18:16

    PHX

    3.0h

    21:16

    PDX

    SMTWTFS

  8. F94299

    Frontier Airlines

    10:51

    MDW

    2.8h

    13:36

    DFW

    ----T-S
    Search

  9. F93253

    Frontier Airlines

    14:59

    DFW

    4.0h

    16:58

    PDX

    -M-W-FS

  10. F94297

    Frontier Airlines

    12:31

    MDW

    2.7h

    15:15

    DFW

    SMTW-F-
    Search

  11. F93253

    Frontier Airlines

    14:59

    DFW

    4.0h

    16:58

    PDX

    -M-W-FS

  12. F92999

    Frontier Airlines

    16:00

    MDW

    2.5h

    18:30

    DFW

    SMTWTFS
    Search

  13. F93253

    Frontier Airlines

    14:59

    DFW

    4.0h

    16:58

    PDX

    -M-W-FS

  14. F92329

    Frontier Airlines

    22:00

    MDW

    4.0h

    23:59

    LAS

    SMTWTFS
    Search

  15. F91105

    Frontier Airlines

    16:00

    LAS

    2.3h

    18:18

    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 price$61
Cheapest return ticket price$105

FAQs for Midway International Airport to Portland International Airport Flights

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

    It takes around 5 hours 3 minutes to fly from Midway International Airport (MDW) to Portland International Airport (PDX).

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

    There are around 2 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 $243 in July, 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 $420 in May, the most expensive month to book this route.

  • What time does the earliest flight from Midway International Airport to Portland International Airport depart?

    The earliest flight departs from Midway International Airport (MDW) at 09:05 and arrives in Portland International Airport (PDX) at 11:20.

  • What time does the latest flight from Midway International Airport to Portland International Airport depart?

    The latest flight departs from Midway International Airport (MDW) at 21:50 and arrives in Portland International Airport (PDX) at 00:10.

  • 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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