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

Search for flights from Portland to Chicago. Find affordable one-way or round-trip flights.

  • One way
  • Round-trip
sortSort by: Lowest Price
  • Sort by: Lowest Price
  • Sort by: Earliest Flight
      • PDX00:59
        19h 6m
        1 stop
        MDW22:05
        Portland - Chicago|Tue, Apr 30|Frontier Airlines
        CNY 57CNY 90
        36% OFF
        36% OFF
        CNY 90CNY 57
      • PDX00:59
        8h 39m
        1 stop
        MDW11:38
        Portland - Chicago|Tue, May 14|Frontier Airlines
        CNY 59CNY 90
        35% OFF
        35% OFF
        CNY 90CNY 59
      • PDX00:49
        13h 49m
        1 stop
        MDW16:38
        Portland - Chicago|Sat, May 11|Frontier Airlines
        CNY 59CNY 90
        34% OFF
        34% OFF
        CNY 90CNY 59
      • PDX00:59
        8h 39m
        1 stop
        MDW11:38
        Portland - Chicago|Wed, May 15|Frontier Airlines
        CNY 62
        CNY 62
      • PDX00:48
        8h 21m
        1 stop
        MDW11:09
        Portland - Chicago|Wed, May 29|Frontier Airlines
        CNY 64
        CNY 64
      • PDX18:05
        13h 17m
        1 stop
        MDW09:22
        Portland - Chicago|Tue, May 7|Frontier Airlines
        CNY 65
        CNY 65
      • PDX18:06
        12h 25m
        1 stop
        MDW08:31
        Portland - Chicago|Sat, May 4|Frontier Airlines
        CNY 67
        CNY 67
      • PDX10:10
        23h 26m
        1 stop
        MDW11:36
        Portland - Chicago|Mon, May 13|Frontier Airlines
        CNY 70
        CNY 70
      • PDX00:59
        8h 39m
        1 stop
        MDW11:38
        Portland - Chicago|Mon, May 6|Frontier Airlines
        CNY 73
        CNY 73
      • PDX00:59
        8h 39m
        1 stop
        MDW11:38
        Portland - Chicago|Wed, May 1|Frontier Airlines
        CNY 73
        CNY 73
      • PDX13:00
        3h 5m
        Direct
        MDW14:00
        Portland - Chicago|Wed, May 1|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

View airlines operating flights from Portland to Chicago. Compare prices and find the airline that meets your travel needs to enjoy a comfortable journey.

Frontier Airlines
From US$57
Alaska Airlines
From US$102
Delta Air Lines
From US$112
American Airlines
From US$122
United Airlines
From US$148
Southwest Airlines
From US$192
Spirit Airlines
From US$230
Sun Country Airlines
From US$241
ANA airlines
Find more flights and airlines

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

Explore other flights from Portland to Chicago. Find the best alternative flight.

  • Cheapest
    Spirit Airlines
    PDX
    23:30
    3h 50m
    Direct
    ORD
    05:20
    Portland International Airport - O'Hare International Airport
    Sat, May 11Spirit Airlines
    US$46
  • Spirit Airlines
    PDX
    23:30
    3h 50m
    Direct
    ORD
    05:20
    Portland International Airport - O'Hare International Airport
    Sat, May 11Spirit Airlines
    US$46
    Find More Flights
Flight Schedule from Portland International Airport to Midway International Airport

Check on the flight schedule from Portland to Chicago to find the flight that matches your travel plan.

Flight info.
Departure
Arrival
Weekly Schedule

  1. F91790

    Frontier Airlines

    00:48

    PDX

    2.6h

    04:24

    DEN

    SMTWTFS
    Search

  2. F92946

    Frontier Airlines

    17:56

    DEN

    2.4h

    21:18

    MDW

    -M-W--S

  3. F91790

    Frontier Airlines

    00:48

    PDX

    2.6h

    04:24

    DEN

    SMTWTFS
    Search

  4. F91592

    Frontier Airlines

    18:54

    DEN

    2.4h

    22:19

    MDW

    -----F-

  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. DL1447

    Delta Air Lines

    06:20

    PDX

    3.3h

    11:36

    MSP

    SMTWTFS
    Search

  8. DL3970

    Delta Air Lines

    15:30

    MSP

    1.6h

    17:04

    MDW

    SMTWT-S

  9. AS2374

    Alaska Airlines

    10:25

    PDX

    1.8h

    12:13

    SFO

    SMTWTFS
    Search

  10. F94042

    Frontier Airlines

    09:03

    SFO

    4.2h

    15:14

    MDW

    SMTWTFS

  11. F93930

    Frontier Airlines

    11:30

    PDX

    1.8h

    13:18

    SFO

    SMTWTFS
    Search

  12. F94042

    Frontier Airlines

    09:03

    SFO

    4.2h

    15:14

    MDW

    SMTWTFS

  13. F92176

    Frontier Airlines

    15:24

    PDX

    2.6h

    19:00

    DEN

    ---W--S
    Search

  14. F92210

    Frontier Airlines

    07:58

    DEN

    2.4h

    11:20

    MDW

    SMTWTFS

  15. F92176

    Frontier Airlines

    15:24

    PDX

    2.6h

    19:00

    DEN

    ---W--S
    Search

  16. F92946

    Frontier Airlines

    17:56

    DEN

    2.4h

    21:18

    MDW

    -M-W--S

  17. AS794

    Alaska Airlines

    15:44

    PDX

    2.8h

    19:29

    DEN

    SMTWTFS
    Search

  18. F92946

    Frontier Airlines

    17:56

    DEN

    2.4h

    21:18

    MDW

    -M-W--S

  19. F93254

    Frontier Airlines

    18:14

    PDX

    3.7h

    23:55

    DFW

    -M-W-FS
    Search

  20. F93000

    Frontier Airlines

    18:40

    DFW

    2.4h

    21:02

    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$57
Cheapest return ticket price$119

FAQs for Portland International Airport to Midway International Airport Flights

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

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

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

    There are around 1 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 $816 in April, 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 $816 in April, the most expensive month to book this route.

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

    The earliest flight departs from Portland International Airport (PDX) at 07:00 and arrives in Midway International Airport (MDW) at 12:50.

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

    The latest flight departs from Portland International Airport (PDX) at 17:05 and arrives in Midway International Airport (MDW) at 01:35.

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

  • 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 346 flights per month.

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