Flight Schedules from Chicago to Portland

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Flight Schedules

Last Updated: Thu, 2 May, 2024

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    • Total Duration
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      • Availability
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 19:35 - 22:08
        ORD - PDX
      • 19:35 (ORD)Chicago O'Hare International Airport
      • 22:08 (PDX)Portland Airport
      • United Airlines (UA 426)Boeing 737 800
      • 4h 33m
      • Direct
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 07:15 - 09:35
        ORD - PDX
      • 07:15 (ORD)Chicago O'Hare International Airport
      • 09:35 (PDX)Portland Airport
      • United Airlines (UA 1500)Boeing 737 800
      • 4h 20m
      • Direct
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 09:15 - 11:35
        ORD - PDX
      • 09:15 (ORD)Chicago O'Hare International Airport
      • 11:35 (PDX)Portland Airport
      • United Airlines (UA 1851)Boeing 737 800
      • 4h 20m
      • Direct
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 09:55 - 12:15
        ORD - PDX
      • 09:55 (ORD)Chicago O'Hare International Airport
      • 12:15 (PDX)Portland Airport
      • American Airlines (AA 2232)Boeing 737 800
      • 4h 20m
      • Direct
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 12:45 - 17:38
        ORD - PDX
      • 12:45 (ORD)Chicago O'Hare International Airport
      • 17:38 (PDX)Portland Airport
      • United Airlines (UA 2662)Boeing 757 300 Series
      • 6h 53m
      • Direct
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 757 300 Series
      • 12:55 - 15:15
        ORD - PDX
      • 12:55 (ORD)Chicago O'Hare International Airport
      • 15:15 (PDX)Portland Airport
      • United Airlines (UA 2282)Boeing 737 800
      • 4h 20m
      • Direct
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 13:10 - 15:54
        ORD - PDX
      • 13:10 (ORD)Chicago O'Hare International Airport
      • 15:54 (PDX)Portland Airport
      • Alaska Airlines (AS 325)Boeing 737
      • 4h 44m
      • Direct
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737
      • 14:15 - 22:15
        ORD - PDX
      • 14:15 (ORD)Chicago O'Hare International Airport
      • 22:15 (PDX)Portland Airport
      • United Airlines (UA 2151)Boeing 737 900
      • 10h
      • Direct
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 900
      • 15:20 - 17:45
        MDW - PDX
      • 15:20 (MDW)Chicago Midway Airport
      • 17:45 (PDX)Portland Airport
      • Southwest Airlines (WN 5616)Boeing 737 800
      • 4h 25m
      • Direct
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 800
      • 15:45 - 18:05
        ORD - PDX
      • 15:45 (ORD)Chicago O'Hare International Airport
      • 18:05 (PDX)Portland Airport
      • United Airlines (UA 1698)Boeing 737 800
      • 4h 20m
      • Direct
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 15:55 - 18:15
        MDW - PDX
      • 15:55 (MDW)Chicago Midway Airport
      • 18:15 (PDX)Portland Airport
      • Southwest Airlines (WN 4361)Boeing 737 800
      • 4h 20m
      • Direct
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 16:30 - 18:55
        MDW - PDX
      • 16:30 (MDW)Chicago Midway Airport
      • 18:55 (PDX)Portland Airport
      • Southwest Airlines (WN 4361)Boeing 737 700
      • 4h 25m
      • Direct
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 18:25 - 20:45
        MDW - PDX
      • 18:25 (MDW)Chicago Midway Airport
      • 20:45 (PDX)Portland Airport
      • Southwest Airlines (WN 5616)Boeing 737 800
      • 4h 20m
      • Direct
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 800

      Connecting Flights

      • 19:25 - 21:05+ 1
        MDW - DEN
        22:25 - 00:05+ 1
        DEN - PDX
      • 19:25 (MDW)Chicago Midway Airport
        22:25 (DEN)Denver Intl Airport
      • 21:05 (DEN)Denver Intl Airport + 1
        00:05 (PDX)Portland Airport
      • Southwest Airlines (WN 2131)Boeing 737 800
        Southwest Airlines (WN 3676)Boeing 737 Max 8 Passenger
      • 6h 40m (1h 20m)
      • DEN Denver 1h 20m
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 05:35 - 07:15
        MDW - PHX
        08:40 - 11:30
        PHX - PDX
      • 05:35 (MDW)Chicago Midway Airport
        08:40 (PHX)Phoenix Sky Harbor Intl Airport
      • 07:15 (PHX)Phoenix Sky Harbor Intl Airport
        11:30 (PDX)Portland Airport
      • Southwest Airlines (WN 2273)Boeing 737 700
        Southwest Airlines (WN 747)Boeing 737 800
      • 7h 55m (1h 25m)
      • PHX Phoenix 1h 25m
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:50 - 07:30
        MDW - DEN
        09:40 - 11:20
        DEN - PDX
      • 05:50 (MDW)Chicago Midway Airport
        09:40 (DEN)Denver Intl Airport
      • 07:30 (DEN)Denver Intl Airport
        11:20 (PDX)Portland Airport
      • Southwest Airlines (WN 1697)Boeing 737 700
        Southwest Airlines (WN 3673)Boeing 737 800
      • 7h 30m (2h 10m)
      • DEN Denver 2h 10m
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 06:15 - 08:35
        MDW - DAL
        11:00 - 12:50
        DAL - PDX
      • 06:15 (MDW)Chicago Midway Airport
        11:00 (DAL)Dallas/Fort Worth Love Field Airport
      • 08:35 (DAL)Dallas/Fort Worth Love Field Airport
        12:50 (PDX)Portland Airport
      • Southwest Airlines (WN 1102)Boeing 737 800
        Southwest Airlines (WN 1883)Boeing 737 700
      • 8h 35m (2h 25m)
      • DAL Dallas 2h 25m
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:30 - 09:10
        MDW - OAK
        10:00 - 11:40
        OAK - PDX
      • 06:30 (MDW)Chicago Midway Airport
        10:00 (OAK)Oakland International Airport
      • 09:10 (OAK)Oakland International Airport
        11:40 (PDX)Portland Airport
      • Southwest Airlines (WN 5472)Boeing 737 700
        Southwest Airlines (WN 3444)Boeing 737 700
      • 7h 10m (50m)
      • OAK Oakland 50m
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 06:30 - 08:15
        ORD - PHX
        09:15 - 11:55
        PHX - PDX
      • 06:30 (ORD)Chicago O'Hare International Airport
        09:15 (PHX)Phoenix Sky Harbor Intl Airport
      • 08:15 (PHX)Phoenix Sky Harbor Intl Airport
        11:55 (PDX)Portland Airport
      • Southwest Airlines (WN 5245)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 747)Boeing 737 700
      • 7h 25m (1h)
      • PHX Phoenix 1h
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 07:15 - 09:00
        ORD - DEN
        12:15 - 13:55
        DEN - PDX
      • 07:15 (ORD)Chicago O'Hare International Airport
        12:15 (DEN)Denver Intl Airport
      • 09:00 (DEN)Denver Intl Airport
        13:55 (PDX)Portland Airport
      • Southwest Airlines (WN 1260)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2739)Boeing 737 Max 8 Passenger
      • 8h 40m (3h 15m)
      • DEN Denver 3h 15m
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 07:20 - 09:55
        MDW - OAK
        11:45 - 13:30
        OAK - PDX
      • 07:20 (MDW)Chicago Midway Airport
        11:45 (OAK)Oakland International Airport
      • 09:55 (OAK)Oakland International Airport
        13:30 (PDX)Portland Airport
      • Southwest Airlines (WN 4212)Boeing 737 700
        Southwest Airlines (WN 367)Boeing 737 700
      • 8h 10m (1h 50m)
      • OAK Oakland 1h 50m
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 07:30 - 10:00
        ORD - DAL
        11:00 - 12:50
        DAL - PDX
      • 07:30 (ORD)Chicago O'Hare International Airport
        11:00 (DAL)Dallas/Fort Worth Love Field Airport
      • 10:00 (DAL)Dallas/Fort Worth Love Field Airport
        12:50 (PDX)Portland Airport
      • Southwest Airlines (WN 5820)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1883)Boeing 737 700
      • 7h 20m (1h)
      • DAL Dallas 1h
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 08:15 - 09:55
        MDW - DEN
        12:15 - 13:55
        DEN - PDX
      • 08:15 (MDW)Chicago Midway Airport
        12:15 (DEN)Denver Intl Airport
      • 09:55 (DEN)Denver Intl Airport
        13:55 (PDX)Portland Airport
      • Southwest Airlines (WN 1699)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2739)Boeing 737 Max 8 Passenger
      • 7h 40m (2h 20m)
      • DEN Denver 2h 20m
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 09:35 - 11:15
        MDW - DEN
        12:15 - 13:55
        DEN - PDX
      • 09:35 (MDW)Chicago Midway Airport
        12:15 (DEN)Denver Intl Airport
      • 11:15 (DEN)Denver Intl Airport
        13:55 (PDX)Portland Airport
      • Southwest Airlines (WN 2203)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2739)Boeing 737 Max 8 Passenger
      • 6h 20m (1h)
      • DEN Denver 1h
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 09:35 - 11:15
        MDW - DEN
        14:40 - 16:20
        DEN - PDX
      • 09:35 (MDW)Chicago Midway Airport
        14:40 (DEN)Denver Intl Airport
      • 11:15 (DEN)Denver Intl Airport
        16:20 (PDX)Portland Airport
      • Southwest Airlines (WN 2203)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 3676)Boeing 737 Max 8 Passenger
      • 8h 45m (3h 25m)
      • DEN Denver 3h 25m
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 09:35 - 12:15
        MDW - SJC
        13:00 - 14:40
        SJC - PDX
      • 09:35 (MDW)Chicago Midway Airport
        13:00 (SJC)San Jose International Airport
      • 12:15 (SJC)San Jose International Airport
        14:40 (PDX)Portland Airport
      • Southwest Airlines (WN 4351)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 725)Boeing 737 700
      • 7h 05m (45m)
      • SJC San Jose 45m
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 09:40 - 11:25
        MDW - PHX
        14:20 - 17:05
        PHX - PDX
      • 09:40 (MDW)Chicago Midway Airport
        14:20 (PHX)Phoenix Sky Harbor Intl Airport
      • 11:25 (PHX)Phoenix Sky Harbor Intl Airport
        17:05 (PDX)Portland Airport
      • Southwest Airlines (WN 3815)Boeing 737 800
        Southwest Airlines (WN 4142)Boeing 737 700
      • 9h 25m (2h 55m)
      • PHX Phoenix 2h 55m
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 10:20 - 12:10
        MDW - LAS
        14:00 - 16:35
        LAS - PDX
      • 10:20 (MDW)Chicago Midway Airport
        14:00 (LAS)Las Vegas McCarran International Airport
      • 12:10 (LAS)Las Vegas McCarran International Airport
        16:35 (PDX)Portland Airport
      • Southwest Airlines (WN 257)Boeing 737 800
        Southwest Airlines (WN 3678)Boeing 737 800
      • 8h 15m (1h 50m)
      • LAS Las Vegas 1h 50m
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 11:05 - 12:50
        MDW - PHX
        13:35 - 16:15
        PHX - PDX
      • 11:05 (MDW)Chicago Midway Airport
        13:35 (PHX)Phoenix Sky Harbor Intl Airport
      • 12:50 (PHX)Phoenix Sky Harbor Intl Airport
        16:15 (PDX)Portland Airport
      • Southwest Airlines (WN 3137)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 5962)Boeing 737 700
      • 7h 10m (45m)
      • PHX Phoenix 45m
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 11:05 - 13:05
        MDW - LAS
        15:35 - 17:55
        LAS - PDX
      • 11:05 (MDW)Chicago Midway Airport
        15:35 (LAS)Las Vegas McCarran International Airport
      • 13:05 (LAS)Las Vegas McCarran International Airport
        17:55 (PDX)Portland Airport
      • Southwest Airlines (WN 240)Boeing 737 800
        Southwest Airlines (WN 1413)Boeing 737 700
      • 8h 50m (2h 30m)
      • LAS Las Vegas 2h 30m
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 11:25 - 13:15
        ORD - DEN
        14:40 - 16:20
        DEN - PDX
      • 11:25 (ORD)Chicago O'Hare International Airport
        14:40 (DEN)Denver Intl Airport
      • 13:15 (DEN)Denver Intl Airport
        16:20 (PDX)Portland Airport
      • Southwest Airlines (WN 1752)Boeing 737 700
        Southwest Airlines (WN 3676)Boeing 737 Max 8 Passenger
      • 6h 55m (1h 25m)
      • DEN Denver 1h 25m
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 11:35 - 13:15
        MDW - PHX
        14:55 - 17:35
        PHX - PDX
      • 11:35 (MDW)Chicago Midway Airport
        14:55 (PHX)Phoenix Sky Harbor Intl Airport
      • 13:15 (PHX)Phoenix Sky Harbor Intl Airport
        17:35 (PDX)Portland Airport
      • Southwest Airlines (WN 3137)Boeing 737 700
        Southwest Airlines (WN 2525)Boeing 737 700
      • 8h (1h 40m)
      • PHX Phoenix 1h 40m
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 12:05 - 14:00
        MDW - LAS
        15:35 - 17:55
        LAS - PDX
      • 12:05 (MDW)Chicago Midway Airport
        15:35 (LAS)Las Vegas McCarran International Airport
      • 14:00 (LAS)Las Vegas McCarran International Airport
        17:55 (PDX)Portland Airport
      • Southwest Airlines (WN 2697)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1413)Boeing 737 700
      • 7h 50m (1h 35m)
      • LAS Las Vegas 1h 35m
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 12:20 - 14:15
        MDW - LAS
        17:00 - 19:25
        LAS - PDX
      • 12:20 (MDW)Chicago Midway Airport
        17:00 (LAS)Las Vegas McCarran International Airport
      • 14:15 (LAS)Las Vegas McCarran International Airport
        19:25 (PDX)Portland Airport
      • Southwest Airlines (WN 2697)Boeing 737 800
        Southwest Airlines (WN 1413)Boeing 737 Max 8 Passenger
      • 9h 05m (2h 45m)
      • LAS Las Vegas 2h 45m
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 12:30 - 14:05
        MDW - DEN
        16:55 - 18:40
        DEN - PDX
      • 12:30 (MDW)Chicago Midway Airport
        16:55 (DEN)Denver Intl Airport
      • 14:05 (DEN)Denver Intl Airport
        18:40 (PDX)Portland Airport
      • Southwest Airlines (WN 1701)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 6122)Boeing 737 800
      • 8h 10m (2h 50m)
      • DEN Denver 2h 50m
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 13:40 - 15:35
        MDW - LAS
        17:00 - 19:25
        LAS - PDX
      • 13:40 (MDW)Chicago Midway Airport
        17:00 (LAS)Las Vegas McCarran International Airport
      • 15:35 (LAS)Las Vegas McCarran International Airport
        19:25 (PDX)Portland Airport
      • Southwest Airlines (WN 2637)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1413)Boeing 737 Max 8 Passenger
      • 7h 45m (1h 25m)
      • LAS Las Vegas 1h 25m
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 14:30 - 16:00
        MDW - DEN
        16:55 - 18:40
        DEN - PDX
      • 14:30 (MDW)Chicago Midway Airport
        16:55 (DEN)Denver Intl Airport
      • 16:00 (DEN)Denver Intl Airport
        18:40 (PDX)Portland Airport
      • Southwest Airlines (WN 2197)Boeing 737 800
        Southwest Airlines (WN 6122)Boeing 737 800
      • 6h 10m (55m)
      • DEN Denver 55m
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 14:45 - 16:25
        MDW - PHX
        17:35 - 20:15
        PHX - PDX
      • 14:45 (MDW)Chicago Midway Airport
        17:35 (PHX)Phoenix Sky Harbor Intl Airport
      • 16:25 (PHX)Phoenix Sky Harbor Intl Airport
        20:15 (PDX)Portland Airport
      • Southwest Airlines (WN 3818)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1156)Boeing 737 700
      • 7h 30m (1h 10m)
      • PHX Phoenix 1h 10m
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 14:45 - 16:20
        MDW - DEN
        18:45 - 20:25
        DEN - PDX
      • 14:45 (MDW)Chicago Midway Airport
        18:45 (DEN)Denver Intl Airport
      • 16:20 (DEN)Denver Intl Airport
        20:25 (PDX)Portland Airport
      • Southwest Airlines (WN 2197)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 3675)Boeing 737 800
      • 7h 40m (2h 25m)
      • DEN Denver 2h 25m
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 15:10 - 17:10
        ORD - LAS
        18:45 - 21:05
        LAS - PDX
      • 15:10 (ORD)Chicago O'Hare International Airport
        18:45 (LAS)Las Vegas McCarran International Airport
      • 17:10 (LAS)Las Vegas McCarran International Airport
        21:05 (PDX)Portland Airport
      • Southwest Airlines (WN 2491)Boeing 737 800
        Southwest Airlines (WN 1413)Boeing 737 700
      • 7h 55m (1h 35m)
      • LAS Las Vegas 1h 35m
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 15:25 - 17:05
        MDW - PHX
        19:30 - 22:10
        PHX - PDX
      • 15:25 (MDW)Chicago Midway Airport
        19:30 (PHX)Phoenix Sky Harbor Intl Airport
      • 17:05 (PHX)Phoenix Sky Harbor Intl Airport
        22:10 (PDX)Portland Airport
      • Southwest Airlines (WN 3818)Boeing 737 800
        Southwest Airlines (WN 5122)Boeing 737 Max 8 Passenger
      • 8h 45m (2h 25m)
      • PHX Phoenix 2h 25m
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 15:50 - 17:30
        MDW - PHX
        19:30 - 22:10
        PHX - PDX
      • 15:50 (MDW)Chicago Midway Airport
        19:30 (PHX)Phoenix Sky Harbor Intl Airport
      • 17:30 (PHX)Phoenix Sky Harbor Intl Airport
        22:10 (PDX)Portland Airport
      • Southwest Airlines (WN 3818)Boeing 737 800
        Southwest Airlines (WN 5122)Boeing 737 700
      • 8h 20m (2h)
      • PHX Phoenix 2h
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 16:00 - 18:00
        ORD - LAS
        20:50 - 23:10
        LAS - PDX
      • 16:00 (ORD)Chicago O'Hare International Airport
        20:50 (LAS)Las Vegas McCarran International Airport
      • 18:00 (LAS)Las Vegas McCarran International Airport
        23:10 (PDX)Portland Airport
      • Southwest Airlines (WN 2491)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 4563)Boeing 737 700
      • 9h 10m (2h 50m)
      • LAS Las Vegas 2h 50m
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 16:00 - 18:00
        MDW - LAS
        20:50 - 23:10
        LAS - PDX
      • 16:00 (MDW)Chicago Midway Airport
        20:50 (LAS)Las Vegas McCarran International Airport
      • 18:00 (LAS)Las Vegas McCarran International Airport
        23:10 (PDX)Portland Airport
      • Southwest Airlines (WN 2454)Boeing 737 800
        Southwest Airlines (WN 4563)Boeing 737 700
      • 9h 10m (2h 50m)
      • LAS Las Vegas 2h 50m
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 16:20 - 18:10
        ORD - DEN
        21:50 - 23:30
        DEN - PDX
      • 16:20 (ORD)Chicago O'Hare International Airport
        21:50 (DEN)Denver Intl Airport
      • 18:10 (DEN)Denver Intl Airport
        23:30 (PDX)Portland Airport
      • Southwest Airlines (WN 5312)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 3676)Boeing 737 Max 8 Passenger
      • 9h 10m (3h 40m)
      • DEN Denver 3h 40m
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 16:20 - 18:00
        MDW - PHX
        19:50 - 22:30
        PHX - PDX
      • 16:20 (MDW)Chicago Midway Airport
        19:50 (PHX)Phoenix Sky Harbor Intl Airport
      • 18:00 (PHX)Phoenix Sky Harbor Intl Airport
        22:30 (PDX)Portland Airport
      • Southwest Airlines (WN 3818)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 5122)Boeing 737 Max 8 Passenger
      • 8h 10m (1h 50m)
      • PHX Phoenix 1h 50m
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 16:20 - 18:10
        ORD - DEN
        21:10 - 22:50
        DEN - PDX
      • 16:20 (ORD)Chicago O'Hare International Airport
        21:10 (DEN)Denver Intl Airport
      • 18:10 (DEN)Denver Intl Airport
        22:50 (PDX)Portland Airport
      • Southwest Airlines (WN 5312)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 154)Boeing 737 700
      • 8h 30m (3h)
      • DEN Denver 3h
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 16:30 - 19:05
        MDW - OAK
        20:10 - 21:50
        OAK - PDX
      • 16:30 (MDW)Chicago Midway Airport
        20:10 (OAK)Oakland International Airport
      • 19:05 (OAK)Oakland International Airport
        21:50 (PDX)Portland Airport
      • Southwest Airlines (WN 1810)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 3743)Boeing 737 Max 8 Passenger
      • 7h 20m (1h 05m)
      • OAK Oakland 1h 05m
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 16:30 - 18:25
        MDW - LAS
        19:40 - 22:00
        LAS - PDX
      • 16:30 (MDW)Chicago Midway Airport
        19:40 (LAS)Las Vegas McCarran International Airport
      • 18:25 (LAS)Las Vegas McCarran International Airport
        22:00 (PDX)Portland Airport
      • Southwest Airlines (WN 2454)Boeing 737 800
        Southwest Airlines (WN 3680)Boeing 737 Max 8 Passenger
      • 7h 30m (1h 15m)
      • LAS Las Vegas 1h 15m
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 16:40 - 18:25
        MDW - PHX
        21:05 - 23:50
        PHX - PDX
      • 16:40 (MDW)Chicago Midway Airport
        21:05 (PHX)Phoenix Sky Harbor Intl Airport
      • 18:25 (PHX)Phoenix Sky Harbor Intl Airport
        23:50 (PDX)Portland Airport
      • Southwest Airlines (WN 1098)Boeing 737 800
        Southwest Airlines (WN 882)Boeing 737 800
      • 9h 10m (2h 40m)
      • PHX Phoenix 2h 40m
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 17:00 - 18:40+ 1
        MDW - DEN
        22:25 - 00:05+ 1
        DEN - PDX
      • 17:00 (MDW)Chicago Midway Airport
        22:25 (DEN)Denver Intl Airport
      • 18:40 (DEN)Denver Intl Airport + 1
        00:05 (PDX)Portland Airport
      • Southwest Airlines (WN 1703)Boeing 737 700
        Southwest Airlines (WN 3676)Boeing 737 Max 8 Passenger
      • 9h 05m (3h 45m)
      • DEN Denver 3h 45m
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 17:45 - 19:35
        ORD - PHX
        21:05 - 23:50
        PHX - PDX
      • 17:45 (ORD)Chicago O'Hare International Airport
        21:05 (PHX)Phoenix Sky Harbor Intl Airport
      • 19:35 (PHX)Phoenix Sky Harbor Intl Airport
        23:50 (PDX)Portland Airport
      • Southwest Airlines (WN 1296)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 882)Boeing 737 800
      • 8h 05m (1h 30m)
      • PHX Phoenix 1h 30m
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 17:50 - 19:35
        MDW - DEN
        21:10 - 22:50
        DEN - PDX
      • 17:50 (MDW)Chicago Midway Airport
        21:10 (DEN)Denver Intl Airport
      • 19:35 (DEN)Denver Intl Airport
        22:50 (PDX)Portland Airport
      • Southwest Airlines (WN 1703)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 154)Boeing 737 700
      • 7h (1h 35m)
      • DEN Denver 1h 35m
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 18:00 - 19:50
        ORD - DEN
        21:10 - 22:50
        DEN - PDX
      • 18:00 (ORD)Chicago O'Hare International Airport
        21:10 (DEN)Denver Intl Airport
      • 19:50 (DEN)Denver Intl Airport
        22:50 (PDX)Portland Airport
      • Southwest Airlines (WN 1755)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 154)Boeing 737 700
      • 6h 50m (1h 20m)
      • DEN Denver 1h 20m
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 18:00 - 19:50
        ORD - DEN
        21:50 - 23:30
        DEN - PDX
      • 18:00 (ORD)Chicago O'Hare International Airport
        21:50 (DEN)Denver Intl Airport
      • 19:50 (DEN)Denver Intl Airport
        23:30 (PDX)Portland Airport
      • Southwest Airlines (WN 1755)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 3676)Boeing 737 Max 8 Passenger
      • 7h 30m (2h)
      • DEN Denver 2h
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 18:00 - 19:50+ 1
        ORD - DEN
        22:25 - 00:05+ 1
        DEN - PDX
      • 18:00 (ORD)Chicago O'Hare International Airport
        22:25 (DEN)Denver Intl Airport
      • 19:50 (DEN)Denver Intl Airport + 1
        00:05 (PDX)Portland Airport
      • Southwest Airlines (WN 1755)Boeing 737 800
        Southwest Airlines (WN 3676)Boeing 737 Max 8 Passenger
      • 8h 05m (2h 35m)
      • DEN Denver 2h 35m
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 18:10 - 19:55
        MDW - DEN
        21:50 - 23:30
        DEN - PDX
      • 18:10 (MDW)Chicago Midway Airport
        21:50 (DEN)Denver Intl Airport
      • 19:55 (DEN)Denver Intl Airport
        23:30 (PDX)Portland Airport
      • Southwest Airlines (WN 1703)Boeing 737 700
        Southwest Airlines (WN 3676)Boeing 737 Max 8 Passenger
      • 7h 20m (1h 55m)
      • DEN Denver 1h 55m
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 18:10 - 20:05
        MDW - LAS
        20:55 - 23:10
        LAS - PDX
      • 18:10 (MDW)Chicago Midway Airport
        20:55 (LAS)Las Vegas McCarran International Airport
      • 20:05 (LAS)Las Vegas McCarran International Airport
        23:10 (PDX)Portland Airport
      • Southwest Airlines (WN 2455)Boeing 737 800
        Southwest Airlines (WN 3680)Boeing 737 700
      • 7h (50m)
      • LAS Las Vegas 50m
        • M
        • -
        • -
        • T
        • F
        • -
        • -
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