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Flights from Portland to Chicago (PDX to MDW)

Discover alternate routes & cheap one way flights from Portland to Chicago (PDX to MDW) within a departure date range.

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  • USD 305
    Spirit AirlinesFrontier Airlines
    9:41pm - 1:23pm
    Mon Jul 3rd
    13h 42m
    Portland (PDX) → Chicago (MDW)
    1 Stop

    Mon Jul 3rd 2023 Spirit Airlines · NK 1261 Depart at 9:41pm from Portland (PDX) Fly for 2h 18m Arrive at 11:59pm in Las Vegas (LAS)

    Layover in Las Vegas for 7h 52m

    Tue Jul 4th 2023 Frontier Airlines · F9 2114 Depart at 7:51am from Las Vegas (LAS) Fly for 3h 32m Arrive at 1:23pm in Chicago (MDW)

  • USD 419
    Delta Air LinesFrontier Airlines
    10:52pm - 10:15am
    Tue Jul 4th
    57h 23m
    Portland (PDX) → Chicago (MDW)
    3 Stops

    Tue Jul 4th 2023 Delta Air Lines · DL 570 Depart at 10:52pm from Portland (PDX) Fly for 4h 38m Arrive at 6:30am in Atlanta (ATL)

    Layover in Atlanta for 0h 50m

    Wed Jul 5th 2023 Delta Air Lines · DL 1610 Depart at 7:20am from Atlanta (ATL) Fly for 1h 28m Arrive at 8:48am in Orlando (MCO)

    Layover in Orlando for 23h 2m

    Thu Jul 6th 2023 Frontier Airlines · F9 1190 Depart at 7:50am from Orlando (MCO) Fly for 1h 50m Arrive at 9:40am in Raleigh (RDU)

    Layover in Raleigh for 23h 36m

    Fri Jul 7th 2023 Frontier Airlines · F9 1787 Depart at 9:16am from Raleigh (RDU) Fly for 1h 59m Arrive at 10:15am in Chicago (MDW)

  • USD 480
    Delta Air LinesFrontier AirlinesSpirit Airlines
    5:26pm - 12:43pm
    Tue Jul 4th
    41h 17m
    Portland (PDX) → Chicago (MDW)
    3 Stops

    Tue Jul 4th 2023 Delta Air Lines · DL 2631 Depart at 5:26pm from Portland (PDX) Fly for 1h 51m Arrive at 8:17pm in Salt Lake City (SLC)

    Layover in Salt Lake City for 3h 8m

    Tue Jul 4th 2023 Delta Air Lines · DL 1741 Depart at 11:25pm from Salt Lake City (SLC) Fly for 1h 31m Arrive at 11:56pm in Reno (RNO)

    Layover in Reno for 9h 0m

    Wed Jul 5th 2023 Spirit Airlines · NK 2515 Depart at 8:56am from Reno (RNO) Fly for 1h 27m Arrive at 10:23am in Las Vegas (LAS)

    Layover in Las Vegas for 20h 47m

    Thu Jul 6th 2023 Frontier Airlines · F9 2114 Depart at 7:10am from Las Vegas (LAS) Fly for 3h 33m Arrive at 12:43pm in Chicago (MDW)

  • USD 480
    Spirit AirlinesFrontier AirlinesAlaska Airlines
    4:20pm - 12:43pm
    Tue Jul 4th
    42h 23m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 Alaska Airlines · AS 3379 Depart at 4:20pm from Portland (PDX) Fly for 1h 31m Arrive at 5:51pm in Reno (RNO)

    Layover in Reno for 15h 5m

    Wed Jul 5th 2023 Spirit Airlines · NK 2515 Depart at 8:56am from Reno (RNO) Fly for 1h 27m Arrive at 10:23am in Las Vegas (LAS)

    Layover in Las Vegas for 20h 47m

    Thu Jul 6th 2023 Frontier Airlines · F9 2114 Depart at 7:10am from Las Vegas (LAS) Fly for 3h 33m Arrive at 12:43pm in Chicago (MDW)

  • USD 482
    Spirit AirlinesFrontier AirlinesAlaska Airlines
    10:00am - 5:35pm
    Tue Jul 4th
    29h 35m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 Alaska Airlines · AS 300 Depart at 10:00am from Portland (PDX) Fly for 5h 40m Arrive at 6:40pm in Orlando (MCO)

    Layover in Orlando for 15h 40m

    Wed Jul 5th 2023 Spirit Airlines · NK 1902 Depart at 10:20am from Orlando (MCO) Fly for 1h 55m Arrive at 12:15pm in Raleigh (RDU)

    Layover in Raleigh for 4h 21m

    Wed Jul 5th 2023 Frontier Airlines · F9 1787 Depart at 4:36pm from Raleigh (RDU) Fly for 1h 59m Arrive at 5:35pm in Chicago (MDW)

  • USD 485
    Delta Air LinesFrontier Airlines
    11:45am - 7:41pm
    Tue Jul 4th
    29h 56m
    Portland (PDX) → Chicago (MDW)
    3 Stops

    Tue Jul 4th 2023 Delta Air Lines · DL 786 Depart at 11:45am from Portland (PDX) Fly for 4h 48m Arrive at 7:33pm in Atlanta (ATL)

    Layover in Atlanta for 2h 52m

    Tue Jul 4th 2023 Delta Air Lines · DL 1229 Depart at 10:25pm from Atlanta (ATL) Fly for 1h 54m Arrive at 12:19am in Fort Lauderdale (FLL)

    Layover in Fort Lauderdale for 9h 9m

    Wed Jul 5th 2023 Frontier Airlines · F9 2294 Depart at 9:28am from Fort Lauderdale (FLL) Fly for 2h 51m Arrive at 12:19pm in Philadelphia (PHL)

    Layover in Philadelphia for 6h 5m

    Wed Jul 5th 2023 Frontier Airlines · F9 1463 Depart at 6:24pm from Philadelphia (PHL) Fly for 2h 17m Arrive at 7:41pm in Chicago (MDW)

  • USD 486
    Delta Air LinesFrontier Airlines
    5:26pm - 7:41pm
    Tue Jul 4th
    24h 15m
    Portland (PDX) → Chicago (MDW)
    3 Stops

    Tue Jul 4th 2023 Delta Air Lines · DL 2631 Depart at 5:26pm from Portland (PDX) Fly for 1h 51m Arrive at 8:17pm in Salt Lake City (SLC)

    Layover in Salt Lake City for 2h 55m

    Tue Jul 4th 2023 Delta Air Lines · DL 1564 Depart at 11:12pm from Salt Lake City (SLC) Fly for 4h 36m Arrive at 5:48am in Fort Lauderdale (FLL)

    Layover in Fort Lauderdale for 3h 40m

    Wed Jul 5th 2023 Frontier Airlines · F9 2294 Depart at 9:28am from Fort Lauderdale (FLL) Fly for 2h 51m Arrive at 12:19pm in Philadelphia (PHL)

    Layover in Philadelphia for 6h 5m

    Wed Jul 5th 2023 Frontier Airlines · F9 1463 Depart at 6:24pm from Philadelphia (PHL) Fly for 2h 17m Arrive at 7:41pm in Chicago (MDW)

  • USD 491
    Delta Air LinesFrontier AirlinesSpirit Airlines
    1:10pm - 5:35pm
    Tue Jul 4th
    26h 25m
    Portland (PDX) → Chicago (MDW)
    3 Stops

    Tue Jul 4th 2023 Delta Air Lines · DL 863 Depart at 1:10pm from Portland (PDX) Fly for 4h 46m Arrive at 8:56pm in Atlanta (ATL)

    Layover in Atlanta for 2h 34m

    Tue Jul 4th 2023 Delta Air Lines · DL 1155 Depart at 11:30pm from Atlanta (ATL) Fly for 1h 29m Arrive at 12:59am in Orlando (MCO)

    Layover in Orlando for 9h 21m

    Wed Jul 5th 2023 Spirit Airlines · NK 1902 Depart at 10:20am from Orlando (MCO) Fly for 1h 55m Arrive at 12:15pm in Raleigh (RDU)

    Layover in Raleigh for 4h 21m

    Wed Jul 5th 2023 Frontier Airlines · F9 1787 Depart at 4:36pm from Raleigh (RDU) Fly for 1h 59m Arrive at 5:35pm in Chicago (MDW)

  • USD 492
    Delta Air LinesAlaska Airlines
    6:00am - 9:47pm
    Tue Jul 4th
    13h 47m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 Alaska Airlines · AS 1298 Depart at 6:00am from Portland (PDX) Fly for 2h 30m Arrive at 8:30am in Santa Ana (SNA)

    Layover in Santa Ana for 3h 27m

    Tue Jul 4th 2023 Delta Air Lines · DL 807 Depart at 11:57am from Santa Ana (SNA) Fly for 4h 25m Arrive at 7:22pm in Atlanta (ATL)

    Layover in Atlanta for 1h 28m

    Tue Jul 4th 2023 Delta Air Lines · DL 1076 Depart at 8:50pm from Atlanta (ATL) Fly for 1h 57m Arrive at 9:47pm in Chicago (MDW)

  • USD 493
    Delta Air Lines
    11:45am - 9:47pm
    Tue Jul 4th
    8h 2m
    Portland (PDX) → Chicago (MDW)
    1 Stop

    Tue Jul 4th 2023 Delta Air Lines · DL 786 Depart at 11:45am from Portland (PDX) Fly for 4h 48m Arrive at 7:33pm in Atlanta (ATL)

    Layover in Atlanta for 1h 17m

    Tue Jul 4th 2023 Delta Air Lines · DL 1076 Depart at 8:50pm from Atlanta (ATL) Fly for 1h 57m Arrive at 9:47pm in Chicago (MDW)

  • USD 493
    Delta Air Lines
    6:00am - 4:10pm
    Tue Jul 4th
    8h 10m
    Portland (PDX) → Chicago (MDW)
    1 Stop

    Tue Jul 4th 2023 Delta Air Lines · DL 762 Depart at 6:00am from Portland (PDX) Fly for 4h 44m Arrive at 1:44pm in Atlanta (ATL)

    Layover in Atlanta for 1h 29m

    Tue Jul 4th 2023 Delta Air Lines · DL 2118 Depart at 3:13pm from Atlanta (ATL) Fly for 1h 57m Arrive at 4:10pm in Chicago (MDW)

  • USD 493
    Delta Air Lines
    10:52pm - 9:15am
    Tue Jul 4th
    8h 23m
    Portland (PDX) → Chicago (MDW)
    1 Stop

    Tue Jul 4th 2023 Delta Air Lines · DL 570 Depart at 10:52pm from Portland (PDX) Fly for 4h 38m Arrive at 6:30am in Atlanta (ATL)

    Layover in Atlanta for 1h 55m

    Wed Jul 5th 2023 Delta Air Lines · DL 2239 Depart at 8:25am from Atlanta (ATL) Fly for 1h 50m Arrive at 9:15am in Chicago (MDW)

  • USD 493
    Spirit AirlinesFrontier AirlinesAlaska Airlines
    8:50pm - 5:35pm
    Tue Jul 4th
    18h 45m
    Portland (PDX) → Chicago (MDW)
    3 Stops

    Tue Jul 4th 2023 Alaska Airlines · AS 2087 Depart at 8:50pm from Portland (PDX) Fly for 0h 59m Arrive at 9:49pm in Seattle (SEA)

    Layover in Seattle for 1h 21m

    Tue Jul 4th 2023 Alaska Airlines · AS 394 Depart at 11:10pm from Seattle (SEA) Fly for 5h 32m Arrive at 7:42am in Orlando (MCO)

    Layover in Orlando for 2h 38m

    Wed Jul 5th 2023 Spirit Airlines · NK 1902 Depart at 10:20am from Orlando (MCO) Fly for 1h 55m Arrive at 12:15pm in Raleigh (RDU)

    Layover in Raleigh for 4h 21m

    Wed Jul 5th 2023 Frontier Airlines · F9 1787 Depart at 4:36pm from Raleigh (RDU) Fly for 1h 59m Arrive at 5:35pm in Chicago (MDW)

  • USD 495
    Delta Air Lines
    10:52pm - 9:15am
    Mon Jul 3rd
    8h 23m
    Portland (PDX) → Chicago (MDW)
    1 Stop

    Mon Jul 3rd 2023 Delta Air Lines · DL 570 Depart at 10:52pm from Portland (PDX) Fly for 4h 38m Arrive at 6:30am in Atlanta (ATL)

    Layover in Atlanta for 1h 55m

    Tue Jul 4th 2023 Delta Air Lines · DL 2239 Depart at 8:25am from Atlanta (ATL) Fly for 1h 50m Arrive at 9:15am in Chicago (MDW)

  • USD 500
    Frontier AirlinesAlaska Airlines
    10:00am - 7:41pm
    Tue Jul 4th
    31h 41m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 Alaska Airlines · AS 300 Depart at 10:00am from Portland (PDX) Fly for 5h 40m Arrive at 6:40pm in Orlando (MCO)

    Layover in Orlando for 19h 19m

    Wed Jul 5th 2023 Frontier Airlines · F9 1166 Depart at 1:59pm from Orlando (MCO) Fly for 2h 37m Arrive at 4:36pm in Philadelphia (PHL)

    Layover in Philadelphia for 1h 48m

    Wed Jul 5th 2023 Frontier Airlines · F9 1463 Depart at 6:24pm from Philadelphia (PHL) Fly for 2h 17m Arrive at 7:41pm in Chicago (MDW)

  • USD 501
    Frontier AirlinesAlaska Airlines
    10:00am - 12:37pm
    Tue Jul 4th
    24h 37m
    Portland (PDX) → Chicago (MDW)
    1 Stop

    Tue Jul 4th 2023 Alaska Airlines · AS 300 Depart at 10:00am from Portland (PDX) Fly for 5h 40m Arrive at 6:40pm in Orlando (MCO)

    Layover in Orlando for 16h 10m

    Wed Jul 5th 2023 Frontier Airlines · F9 1022 Depart at 10:50am from Orlando (MCO) Fly for 2h 47m Arrive at 12:37pm in Chicago (MDW)

  • USD 509
    Delta Air LinesFrontier Airlines
    10:52pm - 7:41pm
    Tue Jul 4th
    18h 49m
    Portland (PDX) → Chicago (MDW)
    3 Stops

    Tue Jul 4th 2023 Delta Air Lines · DL 570 Depart at 10:52pm from Portland (PDX) Fly for 4h 38m Arrive at 6:30am in Atlanta (ATL)

    Layover in Atlanta for 0h 50m

    Wed Jul 5th 2023 Delta Air Lines · DL 1610 Depart at 7:20am from Atlanta (ATL) Fly for 1h 28m Arrive at 8:48am in Orlando (MCO)

    Layover in Orlando for 5h 11m

    Wed Jul 5th 2023 Frontier Airlines · F9 1166 Depart at 1:59pm from Orlando (MCO) Fly for 2h 37m Arrive at 4:36pm in Philadelphia (PHL)

    Layover in Philadelphia for 1h 48m

    Wed Jul 5th 2023 Frontier Airlines · F9 1463 Depart at 6:24pm from Philadelphia (PHL) Fly for 2h 17m Arrive at 7:41pm in Chicago (MDW)

  • USD 509
    Delta Air LinesFrontier Airlines
    1:10pm - 7:41pm
    Tue Jul 4th
    28h 31m
    Portland (PDX) → Chicago (MDW)
    3 Stops

    Tue Jul 4th 2023 Delta Air Lines · DL 863 Depart at 1:10pm from Portland (PDX) Fly for 4h 46m Arrive at 8:56pm in Atlanta (ATL)

    Layover in Atlanta for 2h 34m

    Tue Jul 4th 2023 Delta Air Lines · DL 1155 Depart at 11:30pm from Atlanta (ATL) Fly for 1h 29m Arrive at 12:59am in Orlando (MCO)

    Layover in Orlando for 13h 0m

    Wed Jul 5th 2023 Frontier Airlines · F9 1166 Depart at 1:59pm from Orlando (MCO) Fly for 2h 37m Arrive at 4:36pm in Philadelphia (PHL)

    Layover in Philadelphia for 1h 48m

    Wed Jul 5th 2023 Frontier Airlines · F9 1463 Depart at 6:24pm from Philadelphia (PHL) Fly for 2h 17m Arrive at 7:41pm in Chicago (MDW)

  • USD 510
    Delta Air LinesFrontier Airlines
    10:52pm - 12:37pm
    Tue Jul 4th
    11h 45m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 Delta Air Lines · DL 570 Depart at 10:52pm from Portland (PDX) Fly for 4h 38m Arrive at 6:30am in Atlanta (ATL)

    Layover in Atlanta for 0h 50m

    Wed Jul 5th 2023 Delta Air Lines · DL 1610 Depart at 7:20am from Atlanta (ATL) Fly for 1h 28m Arrive at 8:48am in Orlando (MCO)

    Layover in Orlando for 2h 2m

    Wed Jul 5th 2023 Frontier Airlines · F9 1022 Depart at 10:50am from Orlando (MCO) Fly for 2h 47m Arrive at 12:37pm in Chicago (MDW)

  • USD 510
    Delta Air LinesFrontier Airlines
    1:10pm - 12:37pm
    Tue Jul 4th
    21h 27m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 Delta Air Lines · DL 863 Depart at 1:10pm from Portland (PDX) Fly for 4h 46m Arrive at 8:56pm in Atlanta (ATL)

    Layover in Atlanta for 2h 34m

    Tue Jul 4th 2023 Delta Air Lines · DL 1155 Depart at 11:30pm from Atlanta (ATL) Fly for 1h 29m Arrive at 12:59am in Orlando (MCO)

    Layover in Orlando for 9h 51m

    Wed Jul 5th 2023 Frontier Airlines · F9 1022 Depart at 10:50am from Orlando (MCO) Fly for 2h 47m Arrive at 12:37pm in Chicago (MDW)

  • USD 511
    Delta Air LinesAmerican Airlines
    7:39am - 12:05pm
    Tue Jul 4th
    26h 26m
    Portland (PDX) → Chicago (MDW)
    3 Stops

    Tue Jul 4th 2023 American Airlines · AA 2311 Depart at 7:39am from Portland (PDX) Fly for 4h 58m Arrive at 3:37pm in Charlotte (CLT)

    Layover in Charlotte for 2h 41m

    Tue Jul 4th 2023 American Airlines · AA 2937 Depart at 6:18pm from Charlotte (CLT) Fly for 1h 55m Arrive at 7:13pm in St. Louis (STL)

    Layover in St. Louis for 10h 47m

    Wed Jul 5th 2023 Delta Air Lines · DL 2298 Depart at 6:00am from St. Louis (STL) Fly for 1h 38m Arrive at 8:38am in Atlanta (ATL)

    Layover in Atlanta for 2h 37m

    Wed Jul 5th 2023 Delta Air Lines · DL 2473 Depart at 11:15am from Atlanta (ATL) Fly for 1h 50m Arrive at 12:05pm in Chicago (MDW)

  • USD 513
    Delta Air Lines
    10:52pm - 4:58pm
    Tue Jul 4th
    16h 6m
    Portland (PDX) → Chicago (MDW)
    3 Stops

    Tue Jul 4th 2023 Delta Air Lines · DL 570 Depart at 10:52pm from Portland (PDX) Fly for 4h 38m Arrive at 6:30am in Atlanta (ATL)

    Layover in Atlanta for 1h 26m

    Wed Jul 5th 2023 Delta Air Lines · DL 2656 Depart at 7:56am from Atlanta (ATL) Fly for 1h 40m Arrive at 8:36am in St. Louis (STL)

    Layover in St. Louis for 2h 9m

    Wed Jul 5th 2023 Delta Air Lines · DL 2429 Depart at 10:45am from St. Louis (STL) Fly for 1h 30m Arrive at 1:15pm in Detroit (DTW)

    Layover in Detroit for 3h 38m

    Wed Jul 5th 2023 Delta Air Lines · DL 3737 Depart at 4:53pm from Detroit (DTW) Fly for 1h 5m Arrive at 4:58pm in Chicago (MDW)

  • USD 513
    Delta Air Lines
    1:51pm - 12:05pm
    Tue Jul 4th
    20h 14m
    Portland (PDX) → Chicago (MDW)
    3 Stops

    Tue Jul 4th 2023 Delta Air Lines · DL 1106 Depart at 1:51pm from Portland (PDX) Fly for 3h 18m Arrive at 7:09pm in Minneapolis (MSP)

    Layover in Minneapolis for 0h 50m

    Tue Jul 4th 2023 Delta Air Lines · DL 2821 Depart at 7:59pm from Minneapolis (MSP) Fly for 1h 33m Arrive at 9:32pm in St. Louis (STL)

    Layover in St. Louis for 8h 28m

    Wed Jul 5th 2023 Delta Air Lines · DL 2298 Depart at 6:00am from St. Louis (STL) Fly for 1h 38m Arrive at 8:38am in Atlanta (ATL)

    Layover in Atlanta for 2h 37m

    Wed Jul 5th 2023 Delta Air Lines · DL 2473 Depart at 11:15am from Atlanta (ATL) Fly for 1h 50m Arrive at 12:05pm in Chicago (MDW)

  • USD 533
    United AirlinesFrontier Airlines
    11:23am - 8:09pm
    Tue Jul 4th
    6h 46m
    Portland (PDX) → Chicago (MDW)
    1 Stop

    Tue Jul 4th 2023 United Airlines · UA 478 Depart at 11:23am from Portland (PDX) Fly for 2h 36m Arrive at 2:59pm in Denver (DEN)

    Layover in Denver for 1h 49m

    Tue Jul 4th 2023 Frontier Airlines · F9 878 Depart at 4:48pm from Denver (DEN) Fly for 2h 21m Arrive at 8:09pm in Chicago (MDW)

  • USD 535
    Frontier AirlinesAlaska Airlines
    7:50am - 8:09pm
    Tue Jul 4th
    10h 19m
    Portland (PDX) → Chicago (MDW)
    1 Stop

    Tue Jul 4th 2023 Alaska Airlines · AS 794 Depart at 7:50am from Portland (PDX) Fly for 2h 37m Arrive at 11:27am in Denver (DEN)

    Layover in Denver for 5h 21m

    Tue Jul 4th 2023 Frontier Airlines · F9 878 Depart at 4:48pm from Denver (DEN) Fly for 2h 21m Arrive at 8:09pm in Chicago (MDW)

  • USD 595
    Delta Air LinesSun Country Airlines
    2:40pm - 8:28am
    Tue Jul 4th
    15h 48m
    Portland (PDX) → Chicago (MDW)
    1 Stop

    Tue Jul 4th 2023 Sun Country Airlines · SY 292 Depart at 2:40pm from Portland (PDX) Fly for 3h 12m Arrive at 7:52pm in Minneapolis (MSP)

    Layover in Minneapolis for 11h 8m

    Wed Jul 5th 2023 Delta Air Lines · DL 4083 Depart at 7:00am from Minneapolis (MSP) Fly for 1h 28m Arrive at 8:28am in Chicago (MDW)

  • USD 654
    Delta Air LinesUnited Airlines
    5:00am - 5:42pm
    Tue Jul 4th
    10h 42m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 United Airlines · UA 2493 Depart at 5:00am from Portland (PDX) Fly for 2h 35m Arrive at 8:35am in Denver (DEN)

    Layover in Denver for 1h 12m

    Tue Jul 4th 2023 United Airlines · UA 459 Depart at 9:47am from Denver (DEN) Fly for 2h 0m Arrive at 12:47pm in Minneapolis (MSP)

    Layover in Minneapolis for 3h 28m

    Tue Jul 4th 2023 Delta Air Lines · DL 2694 Depart at 4:15pm from Minneapolis (MSP) Fly for 1h 27m Arrive at 5:42pm in Chicago (MDW)

  • USD 688
    Delta Air LinesFrontier Airlines
    12:40am - 11:27am
    Tue Jul 4th
    8h 47m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 Frontier Airlines · F9 790 Depart at 12:40am from Portland (PDX) Fly for 2h 35m Arrive at 4:15am in Denver (DEN)

    Layover in Denver for 2h 5m

    Tue Jul 4th 2023 Delta Air Lines · DL 1349 Depart at 6:20am from Denver (DEN) Fly for 2h 0m Arrive at 9:20am in Minneapolis (MSP)

    Layover in Minneapolis for 0h 40m

    Tue Jul 4th 2023 Delta Air Lines · DL 4053 Depart at 10:00am from Minneapolis (MSP) Fly for 1h 27m Arrive at 11:27am in Chicago (MDW)

  • USD 693
    Delta Air LinesUnited Airlines
    4:01pm - 8:28am
    Tue Jul 4th
    14h 27m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 United Airlines · UA 1632 Depart at 4:01pm from Portland (PDX) Fly for 1h 49m Arrive at 5:50pm in San Francisco (SFO)

    Layover in San Francisco for 0h 35m

    Tue Jul 4th 2023 United Airlines · UA 1554 Depart at 6:25pm from San Francisco (SFO) Fly for 3h 46m Arrive at 12:11am in Minneapolis (MSP)

    Layover in Minneapolis for 6h 49m

    Wed Jul 5th 2023 Delta Air Lines · DL 4083 Depart at 7:00am from Minneapolis (MSP) Fly for 1h 28m Arrive at 8:28am in Chicago (MDW)

  • USD 736
    Delta Air LinesFrontier AirlinesAlaska Airlines
    4:05pm - 8:28am
    Tue Jul 4th
    14h 23m
    Portland (PDX) → Chicago (MDW)
    3 Stops

    Tue Jul 4th 2023 Alaska Airlines · AS 2240 Depart at 4:05pm from Portland (PDX) Fly for 2h 29m Arrive at 6:34pm in Santa Ana (SNA)

    Layover in Santa Ana for 2h 26m

    Tue Jul 4th 2023 Frontier Airlines · F9 2778 Depart at 9:00pm from Santa Ana (SNA) Fly for 1h 30m Arrive at 10:30pm in Phoenix (PHX)

    Layover in Phoenix for 2h 27m

    Wed Jul 5th 2023 Delta Air Lines · DL 1002 Depart at 12:57am from Phoenix (PHX) Fly for 2h 58m Arrive at 5:55am in Minneapolis (MSP)

    Layover in Minneapolis for 1h 5m

    Wed Jul 5th 2023 Delta Air Lines · DL 4083 Depart at 7:00am from Minneapolis (MSP) Fly for 1h 28m Arrive at 8:28am in Chicago (MDW)

  • USD 750
    Delta Air LinesAlaska Airlines
    5:00pm - 8:28am
    Tue Jul 4th
    13h 28m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 Alaska Airlines · AS 3366 Depart at 5:00pm from Portland (PDX) Fly for 0h 59m Arrive at 5:59pm in Seattle (SEA)

    Layover in Seattle for 0h 46m

    Tue Jul 4th 2023 Alaska Airlines · AS 386 Depart at 6:45pm from Seattle (SEA) Fly for 3h 14m Arrive at 11:59pm in Minneapolis (MSP)

    Layover in Minneapolis for 7h 1m

    Wed Jul 5th 2023 Delta Air Lines · DL 4083 Depart at 7:00am from Minneapolis (MSP) Fly for 1h 28m Arrive at 8:28am in Chicago (MDW)

  • USD 797
    Delta Air LinesUnited Airlines
    7:05pm - 8:28am
    Tue Jul 4th
    11h 23m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 United Airlines · UA 2482 Depart at 7:05pm from Portland (PDX) Fly for 1h 49m Arrive at 8:54pm in San Francisco (SFO)

    Layover in San Francisco for 3h 16m

    Wed Jul 5th 2023 Delta Air Lines · DL 1081 Depart at 12:10am from San Francisco (SFO) Fly for 3h 39m Arrive at 5:49am in Minneapolis (MSP)

    Layover in Minneapolis for 1h 11m

    Wed Jul 5th 2023 Delta Air Lines · DL 4083 Depart at 7:00am from Minneapolis (MSP) Fly for 1h 28m Arrive at 8:28am in Chicago (MDW)

  • USD 798
    Delta Air LinesAmerican Airlines
    7:30pm - 8:28am
    Tue Jul 4th
    10h 58m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 American Airlines · AA 7575 Depart at 7:30pm from Portland (PDX) Fly for 1h 50m Arrive at 9:20pm in San Francisco (SFO)

    Layover in San Francisco for 2h 50m

    Wed Jul 5th 2023 Delta Air Lines · DL 1081 Depart at 12:10am from San Francisco (SFO) Fly for 3h 39m Arrive at 5:49am in Minneapolis (MSP)

    Layover in Minneapolis for 1h 11m

    Wed Jul 5th 2023 Delta Air Lines · DL 4083 Depart at 7:00am from Minneapolis (MSP) Fly for 1h 28m Arrive at 8:28am in Chicago (MDW)

  • USD 810
    Delta Air Lines
    5:54pm - 8:41am
    Tue Jul 4th
    12h 47m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 Delta Air Lines · DL 3998 Depart at 5:54pm from Portland (PDX) Fly for 1h 6m Arrive at 7:00pm in Seattle (SEA)

    Layover in Seattle for 3h 55m

    Tue Jul 4th 2023 Delta Air Lines · DL 788 Depart at 10:55pm from Seattle (SEA) Fly for 4h 20m Arrive at 6:15am in Detroit (DTW)

    Layover in Detroit for 2h 17m

    Wed Jul 5th 2023 Delta Air Lines · DL 4017 Depart at 8:32am from Detroit (DTW) Fly for 1h 9m Arrive at 8:41am in Chicago (MDW)

  • USD 812
    Delta Air Lines
    5:54pm - 8:28am
    Tue Jul 4th
    12h 34m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 Delta Air Lines · DL 3998 Depart at 5:54pm from Portland (PDX) Fly for 1h 6m Arrive at 7:00pm in Seattle (SEA)

    Layover in Seattle for 5h 35m

    Wed Jul 5th 2023 Delta Air Lines · DL 681 Depart at 12:35am from Seattle (SEA) Fly for 3h 13m Arrive at 5:48am in Minneapolis (MSP)

    Layover in Minneapolis for 1h 12m

    Wed Jul 5th 2023 Delta Air Lines · DL 4083 Depart at 7:00am from Minneapolis (MSP) Fly for 1h 28m Arrive at 8:28am in Chicago (MDW)

  • USD 813
    Delta Air Lines
    3:24pm - 8:28am
    Tue Jul 4th
    15h 4m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 Delta Air Lines · DL 3976 Depart at 3:24pm from Portland (PDX) Fly for 1h 9m Arrive at 4:33pm in Seattle (SEA)

    Layover in Seattle for 8h 2m

    Wed Jul 5th 2023 Delta Air Lines · DL 681 Depart at 12:35am from Seattle (SEA) Fly for 3h 13m Arrive at 5:48am in Minneapolis (MSP)

    Layover in Minneapolis for 1h 12m

    Wed Jul 5th 2023 Delta Air Lines · DL 4083 Depart at 7:00am from Minneapolis (MSP) Fly for 1h 28m Arrive at 8:28am in Chicago (MDW)

  • USD 835
    Delta Air LinesAlaska Airlines
    8:50pm - 8:41am
    Tue Jul 4th
    9h 51m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 Alaska Airlines · AS 2087 Depart at 8:50pm from Portland (PDX) Fly for 0h 59m Arrive at 9:49pm in Seattle (SEA)

    Layover in Seattle for 0h 41m

    Tue Jul 4th 2023 Alaska Airlines · AS 478 Depart at 10:30pm from Seattle (SEA) Fly for 4h 14m Arrive at 5:44am in Detroit (DTW)

    Layover in Detroit for 2h 48m

    Wed Jul 5th 2023 Delta Air Lines · DL 4017 Depart at 8:32am from Detroit (DTW) Fly for 1h 9m Arrive at 8:41am in Chicago (MDW)

  • USD 851
    Delta Air LinesAmerican Airlines
    8:50pm - 8:28am
    Tue Jul 4th
    9h 38m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 American Airlines · AA 7556 Depart at 8:50pm from Portland (PDX) Fly for 0h 59m Arrive at 9:49pm in Seattle (SEA)

    Layover in Seattle for 2h 46m

    Wed Jul 5th 2023 Delta Air Lines · DL 681 Depart at 12:35am from Seattle (SEA) Fly for 3h 13m Arrive at 5:48am in Minneapolis (MSP)

    Layover in Minneapolis for 1h 12m

    Wed Jul 5th 2023 Delta Air Lines · DL 4083 Depart at 7:00am from Minneapolis (MSP) Fly for 1h 28m Arrive at 8:28am in Chicago (MDW)

  • USD 880
    Delta Air Lines
    5:52pm - 8:28am
    Tue Jul 4th
    12h 36m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 Delta Air Lines · DL 1059 Depart at 5:52pm from Portland (PDX) Fly for 2h 32m Arrive at 8:24pm in Los Angeles (LAX)

    Layover in Los Angeles for 3h 1m

    Tue Jul 4th 2023 Delta Air Lines · DL 430 Depart at 11:25pm from Los Angeles (LAX) Fly for 3h 36m Arrive at 5:01am in Minneapolis (MSP)

    Layover in Minneapolis for 1h 59m

    Wed Jul 5th 2023 Delta Air Lines · DL 4083 Depart at 7:00am from Minneapolis (MSP) Fly for 1h 28m Arrive at 8:28am in Chicago (MDW)

  • USD 880
    Delta Air Lines
    5:52pm - 8:41am
    Tue Jul 4th
    12h 49m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 Delta Air Lines · DL 1059 Depart at 5:52pm from Portland (PDX) Fly for 2h 32m Arrive at 8:24pm in Los Angeles (LAX)

    Layover in Los Angeles for 1h 36m

    Tue Jul 4th 2023 Delta Air Lines · DL 407 Depart at 10:00pm from Los Angeles (LAX) Fly for 4h 24m Arrive at 5:24am in Detroit (DTW)

    Layover in Detroit for 3h 8m

    Wed Jul 5th 2023 Delta Air Lines · DL 4017 Depart at 8:32am from Detroit (DTW) Fly for 1h 9m Arrive at 8:41am in Chicago (MDW)

  • USD 880
    Delta Air Lines
    5:52pm - 9:15am
    Tue Jul 4th
    13h 23m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 Delta Air Lines · DL 1059 Depart at 5:52pm from Portland (PDX) Fly for 2h 32m Arrive at 8:24pm in Los Angeles (LAX)

    Layover in Los Angeles for 2h 21m

    Tue Jul 4th 2023 Delta Air Lines · DL 899 Depart at 10:45pm from Los Angeles (LAX) Fly for 4h 29m Arrive at 6:14am in Atlanta (ATL)

    Layover in Atlanta for 2h 11m

    Wed Jul 5th 2023 Delta Air Lines · DL 2239 Depart at 8:25am from Atlanta (ATL) Fly for 1h 50m Arrive at 9:15am in Chicago (MDW)

  • USD 880
    Delta Air Lines
    6:05am - 9:47pm
    Tue Jul 4th
    13h 42m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 Delta Air Lines · DL 2973 Depart at 6:05am from Portland (PDX) Fly for 2h 28m Arrive at 8:33am in Los Angeles (LAX)

    Layover in Los Angeles for 2h 36m

    Tue Jul 4th 2023 Delta Air Lines · DL 715 Depart at 11:09am from Los Angeles (LAX) Fly for 4h 25m Arrive at 6:34pm in Atlanta (ATL)

    Layover in Atlanta for 2h 16m

    Tue Jul 4th 2023 Delta Air Lines · DL 1076 Depart at 8:50pm from Atlanta (ATL) Fly for 1h 57m Arrive at 9:47pm in Chicago (MDW)

  • USD 880
    Delta Air Lines
    6:05am - 9:47pm
    Tue Jul 4th
    13h 42m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 Delta Air Lines · DL 2973 Depart at 6:05am from Portland (PDX) Fly for 2h 28m Arrive at 8:33am in Los Angeles (LAX)

    Layover in Los Angeles for 1h 7m

    Tue Jul 4th 2023 Delta Air Lines · DL 381 Depart at 9:40am from Los Angeles (LAX) Fly for 4h 30m Arrive at 5:10pm in Atlanta (ATL)

    Layover in Atlanta for 3h 40m

    Tue Jul 4th 2023 Delta Air Lines · DL 1076 Depart at 8:50pm from Atlanta (ATL) Fly for 1h 57m Arrive at 9:47pm in Chicago (MDW)

  • USD 880
    Delta Air Lines
    5:52pm - 12:05pm
    Tue Jul 4th
    16h 13m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 Delta Air Lines · DL 1059 Depart at 5:52pm from Portland (PDX) Fly for 2h 32m Arrive at 8:24pm in Los Angeles (LAX)

    Layover in Los Angeles for 3h 21m

    Tue Jul 4th 2023 Delta Air Lines · DL 320 Depart at 11:45pm from Los Angeles (LAX) Fly for 4h 33m Arrive at 7:18am in Atlanta (ATL)

    Layover in Atlanta for 3h 57m

    Wed Jul 5th 2023 Delta Air Lines · DL 2473 Depart at 11:15am from Atlanta (ATL) Fly for 1h 50m Arrive at 12:05pm in Chicago (MDW)

  • USD 902
    American AirlinesFrontier Airlines
    7:25am - 6:46pm
    Tue Jul 4th
    9h 21m
    Portland (PDX) → Chicago (MDW)
    1 Stop

    Tue Jul 4th 2023 American Airlines · AA 2577 Depart at 7:25am from Portland (PDX) Fly for 3h 48m Arrive at 1:13pm in Dallas (DFW)

    Layover in Dallas for 3h 11m

    Tue Jul 4th 2023 Frontier Airlines · F9 1370 Depart at 4:24pm from Dallas (DFW) Fly for 2h 22m Arrive at 6:46pm in Chicago (MDW)

  • USD 926
    Delta Air LinesFrontier Airlines
    1:10pm - 11:55pm
    Tue Jul 4th
    8h 45m
    Portland (PDX) → Chicago (MDW)
    1 Stop

    Tue Jul 4th 2023 Delta Air Lines · DL 863 Depart at 1:10pm from Portland (PDX) Fly for 4h 46m Arrive at 8:56pm in Atlanta (ATL)

    Layover in Atlanta for 1h 59m

    Tue Jul 4th 2023 Frontier Airlines · F9 1354 Depart at 10:55pm from Atlanta (ATL) Fly for 2h 0m Arrive at 11:55pm in Chicago (MDW)

  • USD 944
    Delta Air Lines
    5:17am - 5:42pm
    Tue Jul 4th
    10h 25m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 Delta Air Lines · DL 3806 Depart at 5:17am from Portland (PDX) Fly for 1h 0m Arrive at 6:17am in Seattle (SEA)

    Layover in Seattle for 2h 3m

    Tue Jul 4th 2023 Delta Air Lines · DL 360 Depart at 8:20am from Seattle (SEA) Fly for 3h 27m Arrive at 1:47pm in Minneapolis (MSP)

    Layover in Minneapolis for 2h 28m

    Tue Jul 4th 2023 Delta Air Lines · DL 2694 Depart at 4:15pm from Minneapolis (MSP) Fly for 1h 27m Arrive at 5:42pm in Chicago (MDW)

  • USD 955
    Delta Air Lines
    5:52pm - 9:15am
    Tue Jul 4th
    13h 23m
    Portland (PDX) → Chicago (MDW)
    2 Stops

    Tue Jul 4th 2023 Delta Air Lines · DL 1059 Depart at 5:52pm from Portland (PDX) Fly for 2h 32m Arrive at 8:24pm in Los Angeles (LAX)

    Layover in Los Angeles for 3h 21m

    Tue Jul 4th 2023 Delta Air Lines · DL 320 Depart at 11:45pm from Los Angeles (LAX) Fly for 4h 33m Arrive at 7:18am in Atlanta (ATL)

    Layover in Atlanta for 1h 7m

    Wed Jul 5th 2023 Delta Air Lines · DL 2239 Depart at 8:25am from Atlanta (ATL) Fly for 1h 50m Arrive at 9:15am in Chicago (MDW)

  • USD 962
    Delta Air Lines
    12:35am - 11:27am
    Tue Jul 4th
    8h 52m
    Portland (PDX) → Chicago (MDW)
    1 Stop

    Tue Jul 4th 2023 Delta Air Lines · DL 2802 Depart at 12:35am from Portland (PDX) Fly for 3h 14m Arrive at 5:49am in Minneapolis (MSP)

    Layover in Minneapolis for 4h 11m

    Tue Jul 4th 2023 Delta Air Lines · DL 4053 Depart at 10:00am from Minneapolis (MSP) Fly for 1h 27m Arrive at 11:27am in Chicago (MDW)

  • USD 962
    Delta Air Lines
    6:29am - 5:42pm
    Tue Jul 4th
    9h 13m
    Portland (PDX) → Chicago (MDW)
    1 Stop

    Tue Jul 4th 2023 Delta Air Lines · DL 1379 Depart at 6:29am from Portland (PDX) Fly for 3h 16m Arrive at 11:45am in Minneapolis (MSP)

    Layover in Minneapolis for 4h 30m

    Tue Jul 4th 2023 Delta Air Lines · DL 2694 Depart at 4:15pm from Minneapolis (MSP) Fly for 1h 27m Arrive at 5:42pm in Chicago (MDW)

  • USD 1019
    Delta Air Lines
    10:52pm - 4:10pm
    Mon Jul 3rd
    15h 18m
    Portland (PDX) → Chicago (MDW)
    1 Stop

    Mon Jul 3rd 2023 Delta Air Lines · DL 570 Depart at 10:52pm from Portland (PDX) Fly for 4h 38m Arrive at 6:30am in Atlanta (ATL)

    Layover in Atlanta for 8h 43m

    Tue Jul 4th 2023 Delta Air Lines · DL 2118 Depart at 3:13pm from Atlanta (ATL) Fly for 1h 57m Arrive at 4:10pm in Chicago (MDW)

@sarahbb1
Sarah Belizaire
@sarahbb1

Have flexible travel plans or looking for alternative routes given the chaos? Check out all the connection possibilities via a super helpful site created by @ismaelyws flightlist.io thanks to @andy_travels for the recommendation #travel #flights

@eyupitsjohn
John Ford
@eyupitsjohn

There seem to be lots of sites launching at the moment that promise to find you cheap flights but not many have the professional finish of Flightlist by @ismaelyws #travel #flights

@andy_travels
Andy Travels
@andy_travels

@ismaelyws Just tried out Flightlist for the first time. Really nice idea, well made, and just what I need at the moment 👍

@travelwitbender
Travel With Bender
@travelwitbender

Did you spot my recent article about how to score cheap one way flights? ✈️ FlightList is my new secret tool for discovering cheap routes, within a departure date range. Plus you can also search by country/region for departures & destinations. Powerful! 💪

Explore Flight Options

Cheap Flight Search Tips

Tips to help you find the cheapest flights from Portland to Chicago (PDX to MDW).

  • Book 45-90 days before your departure date.
  • Fly during weekdays (Monday-Thursday).
  • Airfare Sales: Airlines sometimes offer huge discounts and since we take a bottom-up approach these flights will appear first in the results, so check back regularly because they don't usually last long.

Why I Built FlightList

❝As someone who works remotely & travels frequently, I always book one way flights and I'm flexible on my departure dates. I look for the best deals. Most sites require you to enter a specific departure date and clutter the page with uneccessary options, images and ads. I want something simple and minimal which allows me to search by departure date range & display a list of flights with the ability to filter according to my needs. So, I built FlightList to solve my own problem & help other travelers who may have the same frustration. It's how I imagine a flight booking site should be.❞

- Hans Desjarlais, Founder & Creator Hans Desjarlais