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

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

  • One way
  • Round-trip
sortSort: Price (Lowest)
  • Sort: Price (Lowest)
  • Sort: Departure (Earliest)
      • PDX00:49
        13h 49m
        1 stop
        MDW16:38
        Portland - Chicago|Sat, May 11|Frontier Airlines
        £47£90
        48% OFF
        48% OFF
        £90£47
      • PDX00:59
        8h 39m
        1 stop
        MDW11:38
        Portland - Chicago|Tue, May 14|Frontier Airlines
        £49£90
        46% OFF
        46% OFF
        £90£49
      • PDX00:59
        8h 39m
        1 stop
        MDW11:38
        Portland - Chicago|Wed, May 15|Frontier Airlines
        £49£90
        45% OFF
        45% OFF
        £90£49
      • PDX00:48
        8h 21m
        1 stop
        MDW11:09
        Portland - Chicago|Wed, May 29|Frontier Airlines
        £51
        £51
      • PDX18:05
        13h 17m
        1 stop
        MDW09:22
        Portland - Chicago|Tue, May 7|Frontier Airlines
        £53
        £53
      • PDX22:22
        10h 39m
        1 stop
        MDW11:01
        Portland - Chicago|Fri, Jun 7|Frontier Airlines
        £55
        £55
      • PDX10:10
        23h 26m
        1 stop
        MDW11:36
        Portland - Chicago|Mon, May 13|Frontier Airlines
        £56
        £56
      • PDX00:48
        8h 21m
        1 stop
        MDW11:09
        Portland - Chicago|Wed, May 22|Frontier Airlines
        £63
        £63
      • PDX00:48
        18h 18m
        1 stop
        MDW21:06
        Portland - Chicago|Sat, May 25|Frontier Airlines
        £63
        £63
      • PDX19:54
        31h 56m
        1 stop
        MDW05:50
        Portland - Chicago|Fri, May 17|Frontier Airlines
        £64
        £64
      • PDX13:00
        3h 5m
        Direct
        MDW14:00
        Portland - Chicago|Mon, May 13|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 Portland International Airport to 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.

Frontier Airlines
From £47
Alaska Airlines
From £81
Delta Air Lines
From £95
American Airlines
From £98
United Airlines
From £127
Southwest Airlines
From £154
Sun Country Airlines
From £193
ANA airlines
Find more flights and airlines

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

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

  • Cheapest
    Spirit Airlines
    PDX
    23:30
    3h 50m
    Direct
    ORD
    05:20
    Portland International Airport - O'Hare International Airport
    Wed, May 29Spirit Airlines
    £26
  • Spirit Airlines
    PDX
    23:30
    3h 50m
    Direct
    ORD
    05:20
    Portland International Airport - O'Hare International Airport
    Wed, May 29Spirit Airlines
    £26
    Find More Flights
Flight Schedule from Portland International Airport to 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. DL2802

    Delta Air Lines

    00:40

    PDX

    3.3h

    06:00

    MSP

    SMTWTFS
    Search

  2. DL4052

    Delta Air Lines

    07:13

    MSP

    1.6h

    08:47

    MDW

    SMTWTFS

  3. F91790

    Frontier Airlines

    00:48

    PDX

    2.6h

    04:24

    DEN

    SMTWTFS
    Search

  4. F92946

    Frontier Airlines

    17:56

    DEN

    2.4h

    21:18

    MDW

    -M-W--S

  5. F91790

    Frontier Airlines

    00:48

    PDX

    2.6h

    04:24

    DEN

    SMTWTFS
    Search

  6. F92210

    Frontier Airlines

    07:58

    DEN

    2.4h

    11:20

    MDW

    SMTWTFS

  7. AS2374

    Alaska Airlines

    10:25

    PDX

    1.8h

    12:13

    SFO

    SMTWTFS
    Search

  8. F94042

    Frontier Airlines

    16:40

    SFO

    4.2h

    22:51

    MDW

    SMTWTFS

  9. F93930

    Frontier Airlines

    13:31

    PDX

    1.8h

    15:19

    SFO

    SMTWTFS
    Search

  10. F94042

    Frontier Airlines

    16:40

    SFO

    4.2h

    22:51

    MDW

    SMTWTFS

  11. AS794

    Alaska Airlines

    15:44

    PDX

    2.8h

    19:29

    DEN

    SMTWTFS
    Search

  12. F92946

    Frontier Airlines

    17:56

    DEN

    2.4h

    21:18

    MDW

    -M-W--S

  13. F93254

    Frontier Airlines

    18:05

    PDX

    3.6h

    23:44

    DFW

    -M-W-FS
    Search

  14. F93000

    Frontier Airlines

    18:51

    DFW

    2.4h

    21:13

    MDW

    SMTW--S

  15. F91106

    Frontier Airlines

    19:30

    PDX

    2.5h

    21:58

    LAS

    S--WTFS
    Search

  16. F92330

    Frontier Airlines

    00:59

    LAS

    3.6h

    06:33

    MDW

    SMTWTFS

  17. AA1956

    American Airlines

    23:59

    PDX

    3.9h

    05:51

    DFW

    SMTWTFS
    Search

  18. F93000

    Frontier Airlines

    18:51

    DFW

    2.4h

    21:13

    MDW

    SMTW--S
Find more flights and airlines

Portland International Airport to Midway International Airport Flights Info

Flight distance2,814.5km
Cheapest one-way ticket price£47
Cheapest return ticket price£95

FAQs for Portland International Airport to Midway International Airport Flights

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

    It takes around 3 hours 55 minutes to fly from Portland International Airport (PDX) to Portland International Airport(MDW).

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

    There are around 3 daily flights from Portland International Airport (PDX) to Midway International Airport (MDW).

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

    Tickets cost around £211 in June, making it the cheapest month to book. Portland International Airport (PDX) to Midway International Airport (MDW) is a popular route, so don't forget to book your tickets in advance.

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

    The route from Portland International Airport (PDX) to Midway International Airport (MDW) is quite popular. Without considering departure times or holidays, tickets cost around £211 in June, the most expensive month to book this route.

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

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

  • What's the closest airport to Midway International Airport (MDW)?

    The closest airport to Midway International Airport (MDW) is O'Hare International Airport. The distance is around 25km.

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

    Southwest Airlines is a very popular airline operating an average of 410 flights per month.

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