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Flights from Chicago to Portland (ORD to PDX)

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

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  • USD 58
    Spirit Airlines
    8:00pm - 10:30pm
    Wed May 8th
    4h 30m
    Chicago (ORD) → Portland (PDX)
    Direct

    Wed May 8th 2024 Spirit Airlines · NK 822 Depart at 8:00pm from Chicago (ORD) Fly for 4h 30m Arrive at 10:30pm in Portland (PDX)

  • USD 58
    Spirit Airlines
    8:00pm - 10:30pm
    Sat May 11th
    4h 30m
    Chicago (ORD) → Portland (PDX)
    Direct

    Sat May 11th 2024 Spirit Airlines · NK 822 Depart at 8:00pm from Chicago (ORD) Fly for 4h 30m Arrive at 10:30pm in Portland (PDX)

  • USD 76
    Spirit Airlines
    8:00pm - 10:30pm
    Fri May 10th
    4h 30m
    Chicago (ORD) → Portland (PDX)
    Direct

    Fri May 10th 2024 Spirit Airlines · NK 822 Depart at 8:00pm from Chicago (ORD) Fly for 4h 30m Arrive at 10:30pm in Portland (PDX)

  • USD 76
    Spirit Airlines
    8:00pm - 10:30pm
    Thu May 9th
    4h 30m
    Chicago (ORD) → Portland (PDX)
    Direct

    Thu May 9th 2024 Spirit Airlines · NK 822 Depart at 8:00pm from Chicago (ORD) Fly for 4h 30m Arrive at 10:30pm in Portland (PDX)

  • USD 98
    Spirit Airlines
    5:50pm - 12:07am
    Wed May 8th
    8h 17m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Wed May 8th 2024 Spirit Airlines · NK 2525 Depart at 5:50pm from Chicago (ORD) Fly for 4h 1m Arrive at 7:51pm in Las Vegas (LAS)

    Layover in Las Vegas for 1h 57m

    Wed May 8th 2024 Spirit Airlines · NK 1723 Depart at 9:48pm from Las Vegas (LAS) Fly for 2h 19m Arrive at 12:07am in Portland (PDX)

  • USD 98
    Spirit Airlines
    1:13pm - 12:07am
    Wed May 8th
    12h 54m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Wed May 8th 2024 Spirit Airlines · NK 487 Depart at 1:13pm from Chicago (ORD) Fly for 4h 1m Arrive at 3:14pm in Las Vegas (LAS)

    Layover in Las Vegas for 6h 34m

    Wed May 8th 2024 Spirit Airlines · NK 1723 Depart at 9:48pm from Las Vegas (LAS) Fly for 2h 19m Arrive at 12:07am in Portland (PDX)

  • USD 100
    Spirit Airlines
    4:05pm - 12:07am
    Sat May 11th
    10h 2m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Sat May 11th 2024 Spirit Airlines · NK 2525 Depart at 4:05pm from Chicago (ORD) Fly for 4h 2m Arrive at 6:07pm in Las Vegas (LAS)

    Layover in Las Vegas for 3h 41m

    Sat May 11th 2024 Spirit Airlines · NK 1723 Depart at 9:48pm from Las Vegas (LAS) Fly for 2h 19m Arrive at 12:07am in Portland (PDX)

  • USD 119
    Spirit Airlines
    4:44pm - 12:29am
    Thu May 9th
    9h 45m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Thu May 9th 2024 Spirit Airlines · NK 2525 Depart at 4:44pm from Chicago (ORD) Fly for 4h 2m Arrive at 6:46pm in Las Vegas (LAS)

    Layover in Las Vegas for 3h 24m

    Thu May 9th 2024 Spirit Airlines · NK 1723 Depart at 10:10pm from Las Vegas (LAS) Fly for 2h 19m Arrive at 12:29am in Portland (PDX)

  • USD 119
    Spirit Airlines
    1:13pm - 12:07am
    Sat May 11th
    12h 54m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Sat May 11th 2024 Spirit Airlines · NK 487 Depart at 1:13pm from Chicago (ORD) Fly for 4h 1m Arrive at 3:14pm in Las Vegas (LAS)

    Layover in Las Vegas for 6h 34m

    Sat May 11th 2024 Spirit Airlines · NK 1723 Depart at 9:48pm from Las Vegas (LAS) Fly for 2h 19m Arrive at 12:07am in Portland (PDX)

  • USD 138
    Spirit Airlines
    9:36am - 2:37pm
    Wed May 8th
    7h 1m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Wed May 8th 2024 Spirit Airlines · NK 183 Depart at 9:36am from Chicago (ORD) Fly for 4h 0m Arrive at 11:36am in Las Vegas (LAS)

    Layover in Las Vegas for 0h 39m

    Wed May 8th 2024 Spirit Airlines · NK 430 Depart at 12:15pm from Las Vegas (LAS) Fly for 2h 22m Arrive at 2:37pm in Portland (PDX)

  • USD 138
    Spirit Airlines
    1:13pm - 12:31am
    Fri May 10th
    13h 18m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Fri May 10th 2024 Spirit Airlines · NK 487 Depart at 1:13pm from Chicago (ORD) Fly for 4h 1m Arrive at 3:14pm in Las Vegas (LAS)

    Layover in Las Vegas for 6h 58m

    Fri May 10th 2024 Spirit Airlines · NK 1723 Depart at 10:12pm from Las Vegas (LAS) Fly for 2h 19m Arrive at 12:31am in Portland (PDX)

  • USD 141
    Spirit Airlines
    9:36am - 6:01pm
    Thu May 9th
    10h 25m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Thu May 9th 2024 Spirit Airlines · NK 183 Depart at 9:36am from Chicago (ORD) Fly for 4h 0m Arrive at 11:36am in Las Vegas (LAS)

    Layover in Las Vegas for 4h 2m

    Thu May 9th 2024 Spirit Airlines · NK 430 Depart at 3:38pm from Las Vegas (LAS) Fly for 2h 23m Arrive at 6:01pm in Portland (PDX)

  • USD 158
    Spirit Airlines
    1:13pm - 6:13pm
    Fri May 10th
    7h 0m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Fri May 10th 2024 Spirit Airlines · NK 487 Depart at 1:13pm from Chicago (ORD) Fly for 4h 1m Arrive at 3:14pm in Las Vegas (LAS)

    Layover in Las Vegas for 0h 36m

    Fri May 10th 2024 Spirit Airlines · NK 430 Depart at 3:50pm from Las Vegas (LAS) Fly for 2h 23m Arrive at 6:13pm in Portland (PDX)

  • USD 158
    Spirit Airlines
    10:14am - 6:13pm
    Fri May 10th
    9h 59m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Fri May 10th 2024 Spirit Airlines · NK 183 Depart at 10:14am from Chicago (ORD) Fly for 4h 0m Arrive at 12:14pm in Las Vegas (LAS)

    Layover in Las Vegas for 3h 36m

    Fri May 10th 2024 Spirit Airlines · NK 430 Depart at 3:50pm from Las Vegas (LAS) Fly for 2h 23m Arrive at 6:13pm in Portland (PDX)

  • USD 160
    Spirit Airlines
    1:13pm - 8:04pm
    Sat May 11th
    8h 51m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Sat May 11th 2024 Spirit Airlines · NK 487 Depart at 1:13pm from Chicago (ORD) Fly for 4h 1m Arrive at 3:14pm in Las Vegas (LAS)

    Layover in Las Vegas for 2h 29m

    Sat May 11th 2024 Spirit Airlines · NK 426 Depart at 5:43pm from Las Vegas (LAS) Fly for 2h 21m Arrive at 8:04pm in Portland (PDX)

  • USD 161
    Alaska Airlines
    8:35am - 11:09am
    Sat May 11th
    4h 34m
    Chicago (ORD) → Portland (PDX)
    Direct

    Sat May 11th 2024 Alaska Airlines · AS 325 Depart at 8:35am from Chicago (ORD) Fly for 4h 34m Arrive at 11:09am in Portland (PDX)

  • USD 165
    Alaska Airlines
    2:53pm - 5:26pm
    Wed May 8th
    4h 33m
    Chicago (ORD) → Portland (PDX)
    Direct

    Wed May 8th 2024 Alaska Airlines · AS 413 Depart at 2:53pm from Chicago (ORD) Fly for 4h 33m Arrive at 5:26pm in Portland (PDX)

  • USD 165
    Alaska Airlines
    8:35am - 11:09am
    Wed May 8th
    4h 34m
    Chicago (ORD) → Portland (PDX)
    Direct

    Wed May 8th 2024 Alaska Airlines · AS 325 Depart at 8:35am from Chicago (ORD) Fly for 4h 34m Arrive at 11:09am in Portland (PDX)

  • USD 167
    United Airlines
    3:57pm - 6:26pm
    Sat May 11th
    4h 29m
    Chicago (ORD) → Portland (PDX)
    Direct

    Sat May 11th 2024 United Airlines · UA 580 Depart at 3:57pm from Chicago (ORD) Fly for 4h 29m Arrive at 6:26pm in Portland (PDX)

  • USD 167
    United Airlines
    3:57pm - 6:26pm
    Wed May 8th
    4h 29m
    Chicago (ORD) → Portland (PDX)
    Direct

    Wed May 8th 2024 United Airlines · UA 580 Depart at 3:57pm from Chicago (ORD) Fly for 4h 29m Arrive at 6:26pm in Portland (PDX)

  • USD 167
    United Airlines
    12:45pm - 3:17pm
    Sat May 11th
    4h 32m
    Chicago (ORD) → Portland (PDX)
    Direct

    Sat May 11th 2024 United Airlines · UA 1946 Depart at 12:45pm from Chicago (ORD) Fly for 4h 32m Arrive at 3:17pm in Portland (PDX)

  • USD 167
    United Airlines
    12:45pm - 3:17pm
    Wed May 8th
    4h 32m
    Chicago (ORD) → Portland (PDX)
    Direct

    Wed May 8th 2024 United Airlines · UA 1946 Depart at 12:45pm from Chicago (ORD) Fly for 4h 32m Arrive at 3:17pm in Portland (PDX)

  • USD 167
    United Airlines
    9:05am - 11:38am
    Wed May 8th
    4h 33m
    Chicago (ORD) → Portland (PDX)
    Direct

    Wed May 8th 2024 United Airlines · UA 628 Depart at 9:05am from Chicago (ORD) Fly for 4h 33m Arrive at 11:38am in Portland (PDX)

  • USD 167
    United Airlines
    9:05am - 11:38am
    Sat May 11th
    4h 33m
    Chicago (ORD) → Portland (PDX)
    Direct

    Sat May 11th 2024 United Airlines · UA 628 Depart at 9:05am from Chicago (ORD) Fly for 4h 33m Arrive at 11:38am in Portland (PDX)

  • USD 167
    United Airlines
    7:57pm - 10:33pm
    Sat May 11th
    4h 36m
    Chicago (ORD) → Portland (PDX)
    Direct

    Sat May 11th 2024 United Airlines · UA 2497 Depart at 7:57pm from Chicago (ORD) Fly for 4h 36m Arrive at 10:33pm in Portland (PDX)

  • USD 177
    United Airlines
    5:00am - 9:32am
    Sat May 11th
    6h 32m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Sat May 11th 2024 United Airlines · UA 2426 Depart at 5:00am from Chicago (ORD) Fly for 2h 42m Arrive at 6:42am in Denver (DEN)

    Layover in Denver for 1h 3m

    Sat May 11th 2024 United Airlines · UA 1247 Depart at 7:45am from Denver (DEN) Fly for 2h 47m Arrive at 9:32am in Portland (PDX)

  • USD 177
    United Airlines
    5:00am - 9:32am
    Wed May 8th
    6h 32m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Wed May 8th 2024 United Airlines · UA 2426 Depart at 5:00am from Chicago (ORD) Fly for 2h 42m Arrive at 6:42am in Denver (DEN)

    Layover in Denver for 1h 3m

    Wed May 8th 2024 United Airlines · UA 1247 Depart at 7:45am from Denver (DEN) Fly for 2h 47m Arrive at 9:32am in Portland (PDX)

  • USD 177
    United Airlines
    8:50am - 2:52pm
    Wed May 8th
    8h 2m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Wed May 8th 2024 United Airlines · UA 301 Depart at 8:50am from Chicago (ORD) Fly for 4h 45m Arrive at 11:35am in San Francisco (SFO)

    Layover in San Francisco for 1h 20m

    Wed May 8th 2024 United Airlines · UA 2309 Depart at 12:55pm from San Francisco (SFO) Fly for 1h 57m Arrive at 2:52pm in Portland (PDX)

  • USD 177
    United Airlines
    2:36pm - 8:59pm
    Sat May 11th
    8h 23m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Sat May 11th 2024 United Airlines · UA 2733 Depart at 2:36pm from Chicago (ORD) Fly for 2h 48m Arrive at 4:24pm in Denver (DEN)

    Layover in Denver for 2h 51m

    Sat May 11th 2024 United Airlines · UA 498 Depart at 7:15pm from Denver (DEN) Fly for 2h 44m Arrive at 8:59pm in Portland (PDX)

  • USD 184
    Alaska Airlines
    6:00am - 10:55am
    Sat May 11th
    6h 55m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Sat May 11th 2024 Alaska Airlines · AS 333 Depart at 6:00am from Chicago (ORD) Fly for 4h 34m Arrive at 8:34am in Seattle (SEA)

    Layover in Seattle for 1h 26m

    Sat May 11th 2024 Alaska Airlines · AS 2183 Depart at 10:00am from Seattle (SEA) Fly for 0h 55m Arrive at 10:55am in Portland (PDX)

  • USD 192
    Alaska Airlines
    6:00am - 10:55am
    Wed May 8th
    6h 55m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Wed May 8th 2024 Alaska Airlines · AS 333 Depart at 6:00am from Chicago (ORD) Fly for 4h 34m Arrive at 8:34am in Seattle (SEA)

    Layover in Seattle for 1h 26m

    Wed May 8th 2024 Alaska Airlines · AS 2183 Depart at 10:00am from Seattle (SEA) Fly for 0h 55m Arrive at 10:55am in Portland (PDX)

  • USD 197
    Alaska Airlines
    2:53pm - 5:26pm
    Thu May 9th
    4h 33m
    Chicago (ORD) → Portland (PDX)
    Direct

    Thu May 9th 2024 Alaska Airlines · AS 413 Depart at 2:53pm from Chicago (ORD) Fly for 4h 33m Arrive at 5:26pm in Portland (PDX)

  • USD 197
    Alaska Airlines
    8:35am - 11:09am
    Thu May 9th
    4h 34m
    Chicago (ORD) → Portland (PDX)
    Direct

    Thu May 9th 2024 Alaska Airlines · AS 325 Depart at 8:35am from Chicago (ORD) Fly for 4h 34m Arrive at 11:09am in Portland (PDX)

  • USD 202
    United Airlines
    3:57pm - 6:26pm
    Thu May 9th
    4h 29m
    Chicago (ORD) → Portland (PDX)
    Direct

    Thu May 9th 2024 United Airlines · UA 580 Depart at 3:57pm from Chicago (ORD) Fly for 4h 29m Arrive at 6:26pm in Portland (PDX)

  • USD 202
    United Airlines
    7:57pm - 10:33pm
    Thu May 9th
    4h 36m
    Chicago (ORD) → Portland (PDX)
    Direct

    Thu May 9th 2024 United Airlines · UA 2497 Depart at 7:57pm from Chicago (ORD) Fly for 4h 36m Arrive at 10:33pm in Portland (PDX)

  • USD 207
    United Airlines
    3:57pm - 6:26pm
    Fri May 10th
    4h 29m
    Chicago (ORD) → Portland (PDX)
    Direct

    Fri May 10th 2024 United Airlines · UA 580 Depart at 3:57pm from Chicago (ORD) Fly for 4h 29m Arrive at 6:26pm in Portland (PDX)

  • USD 207
    United Airlines
    12:45pm - 3:17pm
    Fri May 10th
    4h 32m
    Chicago (ORD) → Portland (PDX)
    Direct

    Fri May 10th 2024 United Airlines · UA 1946 Depart at 12:45pm from Chicago (ORD) Fly for 4h 32m Arrive at 3:17pm in Portland (PDX)

  • USD 207
    Alaska Airlines
    2:53pm - 5:26pm
    Fri May 10th
    4h 33m
    Chicago (ORD) → Portland (PDX)
    Direct

    Fri May 10th 2024 Alaska Airlines · AS 413 Depart at 2:53pm from Chicago (ORD) Fly for 4h 33m Arrive at 5:26pm in Portland (PDX)

  • USD 207
    Alaska Airlines
    8:35am - 11:09am
    Fri May 10th
    4h 34m
    Chicago (ORD) → Portland (PDX)
    Direct

    Fri May 10th 2024 Alaska Airlines · AS 325 Depart at 8:35am from Chicago (ORD) Fly for 4h 34m Arrive at 11:09am in Portland (PDX)

  • USD 207
    United Airlines
    7:57pm - 10:33pm
    Fri May 10th
    4h 36m
    Chicago (ORD) → Portland (PDX)
    Direct

    Fri May 10th 2024 United Airlines · UA 2497 Depart at 7:57pm from Chicago (ORD) Fly for 4h 36m Arrive at 10:33pm in Portland (PDX)

  • USD 226
    United Airlines
    9:05am - 11:38am
    Thu May 9th
    4h 33m
    Chicago (ORD) → Portland (PDX)
    Direct

    Thu May 9th 2024 United Airlines · UA 628 Depart at 9:05am from Chicago (ORD) Fly for 4h 33m Arrive at 11:38am in Portland (PDX)

  • USD 232
    United Airlines
    12:45pm - 3:17pm
    Thu May 9th
    4h 32m
    Chicago (ORD) → Portland (PDX)
    Direct

    Thu May 9th 2024 United Airlines · UA 1946 Depart at 12:45pm from Chicago (ORD) Fly for 4h 32m Arrive at 3:17pm in Portland (PDX)

  • USD 232
    United Airlines
    9:05am - 11:38am
    Fri May 10th
    4h 33m
    Chicago (ORD) → Portland (PDX)
    Direct

    Fri May 10th 2024 United Airlines · UA 628 Depart at 9:05am from Chicago (ORD) Fly for 4h 33m Arrive at 11:38am in Portland (PDX)

  • USD 269
    United Airlines
    7:57pm - 10:33pm
    Wed May 8th
    4h 36m
    Chicago (ORD) → Portland (PDX)
    Direct

    Wed May 8th 2024 United Airlines · UA 2497 Depart at 7:57pm from Chicago (ORD) Fly for 4h 36m Arrive at 10:33pm in Portland (PDX)

@sarahbb1
Sarah Belizaire
@sarahbb1

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@eyupitsjohn
John Ford
@eyupitsjohn

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@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 Chicago to Portland (ORD to PDX).

  • 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