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Flights from Chicago to Portland (CHI to PDX)

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

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  • USD 58
    Spirit Airlines
    8:34pm - 10:56pm
    Thu Jul 18th
    4h 22m
    Chicago (ORD) → Portland (PDX)
    Direct

    Thu Jul 18th 2024 Spirit Airlines · NK 822 Depart at 8:34pm from Chicago (ORD) Fly for 4h 22m Arrive at 10:56pm in Portland (PDX)

  • USD 58
    Spirit Airlines
    8:34pm - 10:56pm
    Fri Jul 19th
    4h 22m
    Chicago (ORD) → Portland (PDX)
    Direct

    Fri Jul 19th 2024 Spirit Airlines · NK 822 Depart at 8:34pm from Chicago (ORD) Fly for 4h 22m Arrive at 10:56pm in Portland (PDX)

  • USD 93
    Spirit Airlines
    6:19pm - 12:13am
    Fri Jul 19th
    7h 54m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Fri Jul 19th 2024 Spirit Airlines · NK 200 Depart at 6:19pm from Chicago (ORD) Fly for 3h 55m Arrive at 8:14pm in Las Vegas (LAS)

    Layover in Las Vegas for 1h 42m

    Fri Jul 19th 2024 Spirit Airlines · NK 1723 Depart at 9:56pm from Las Vegas (LAS) Fly for 2h 17m Arrive at 12:13am in Portland (PDX)

  • USD 93
    Spirit Airlines
    1:28pm - 9:05pm
    Fri Jul 19th
    9h 37m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Fri Jul 19th 2024 Spirit Airlines · NK 487 Depart at 1:28pm from Chicago (ORD) Fly for 3h 52m Arrive at 3:20pm in Las Vegas (LAS)

    Layover in Las Vegas for 3h 28m

    Fri Jul 19th 2024 Spirit Airlines · NK 430 Depart at 6:48pm from Las Vegas (LAS) Fly for 2h 17m Arrive at 9:05pm in Portland (PDX)

  • USD 93
    Spirit Airlines
    1:28pm - 12:13am
    Fri Jul 19th
    12h 45m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Fri Jul 19th 2024 Spirit Airlines · NK 487 Depart at 1:28pm from Chicago (ORD) Fly for 3h 52m Arrive at 3:20pm in Las Vegas (LAS)

    Layover in Las Vegas for 6h 36m

    Fri Jul 19th 2024 Spirit Airlines · NK 1723 Depart at 9:56pm from Las Vegas (LAS) Fly for 2h 17m Arrive at 12:13am in Portland (PDX)

  • USD 109
    Spirit Airlines
    9:19pm - 8:50am
    Thu Jul 18th
    13h 31m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Thu Jul 18th 2024 Spirit Airlines · NK 489 Depart at 9:19pm from Chicago (ORD) Fly for 4h 26m Arrive at 11:45pm in Los Angeles (LAX)

    Layover in Los Angeles for 6h 42m

    Fri Jul 19th 2024 Spirit Airlines · NK 356 Depart at 6:27am from Los Angeles (LAX) Fly for 2h 23m Arrive at 8:50am in Portland (PDX)

  • USD 109
    Spirit Airlines
    4:07pm - 8:50am
    Thu Jul 18th
    18h 43m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Thu Jul 18th 2024 Spirit Airlines · NK 1786 Depart at 4:07pm from Chicago (ORD) Fly for 4h 24m Arrive at 6:31pm in Los Angeles (LAX)

    Layover in Los Angeles for 11h 56m

    Fri Jul 19th 2024 Spirit Airlines · NK 356 Depart at 6:27am from Los Angeles (LAX) Fly for 2h 23m Arrive at 8:50am in Portland (PDX)

  • USD 125
    Spirit Airlines
    10:38pm - 8:50am
    Fri Jul 19th
    12h 12m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Fri Jul 19th 2024 Spirit Airlines · NK 489 Depart at 10:38pm from Chicago (ORD) Fly for 4h 27m Arrive at 1:05am in Los Angeles (LAX)

    Layover in Los Angeles for 5h 22m

    Sat Jul 20th 2024 Spirit Airlines · NK 356 Depart at 6:27am from Los Angeles (LAX) Fly for 2h 23m Arrive at 8:50am in Portland (PDX)

  • USD 125
    Spirit Airlines
    8:26pm - 8:50am
    Fri Jul 19th
    14h 24m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Fri Jul 19th 2024 Spirit Airlines · NK 1786 Depart at 8:26pm from Chicago (ORD) Fly for 4h 29m Arrive at 10:55pm in Los Angeles (LAX)

    Layover in Los Angeles for 7h 32m

    Sat Jul 20th 2024 Spirit Airlines · NK 356 Depart at 6:27am from Los Angeles (LAX) Fly for 2h 23m Arrive at 8:50am in Portland (PDX)

  • USD 132
    Spirit Airlines
    1:28pm - 9:05pm
    Thu Jul 18th
    9h 37m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Thu Jul 18th 2024 Spirit Airlines · NK 487 Depart at 1:28pm from Chicago (ORD) Fly for 3h 52m Arrive at 3:20pm in Las Vegas (LAS)

    Layover in Las Vegas for 3h 28m

    Thu Jul 18th 2024 Spirit Airlines · NK 430 Depart at 6:48pm from Las Vegas (LAS) Fly for 2h 17m Arrive at 9:05pm in Portland (PDX)

  • USD 132
    Spirit Airlines
    1:28pm - 12:13am
    Thu Jul 18th
    12h 45m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Thu Jul 18th 2024 Spirit Airlines · NK 487 Depart at 1:28pm from Chicago (ORD) Fly for 3h 52m Arrive at 3:20pm in Las Vegas (LAS)

    Layover in Las Vegas for 6h 36m

    Thu Jul 18th 2024 Spirit Airlines · NK 1723 Depart at 9:56pm from Las Vegas (LAS) Fly for 2h 17m Arrive at 12:13am in Portland (PDX)

  • USD 132
    Spirit Airlines
    10:14am - 9:05pm
    Fri Jul 19th
    12h 51m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Fri Jul 19th 2024 Spirit Airlines · NK 183 Depart at 10:14am from Chicago (ORD) Fly for 3h 55m Arrive at 12:09pm in Las Vegas (LAS)

    Layover in Las Vegas for 6h 39m

    Fri Jul 19th 2024 Spirit Airlines · NK 430 Depart at 6:48pm from Las Vegas (LAS) Fly for 2h 17m Arrive at 9:05pm in Portland (PDX)

  • USD 132
    Spirit Airlines
    9:36am - 9:05pm
    Thu Jul 18th
    13h 29m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Thu Jul 18th 2024 Spirit Airlines · NK 183 Depart at 9:36am from Chicago (ORD) Fly for 3h 57m Arrive at 11:33am in Las Vegas (LAS)

    Layover in Las Vegas for 7h 15m

    Thu Jul 18th 2024 Spirit Airlines · NK 430 Depart at 6:48pm from Las Vegas (LAS) Fly for 2h 17m Arrive at 9:05pm in Portland (PDX)

  • USD 132
    Spirit Airlines
    10:14am - 12:13am
    Fri Jul 19th
    15h 59m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Fri Jul 19th 2024 Spirit Airlines · NK 183 Depart at 10:14am from Chicago (ORD) Fly for 3h 55m Arrive at 12:09pm in Las Vegas (LAS)

    Layover in Las Vegas for 9h 47m

    Fri Jul 19th 2024 Spirit Airlines · NK 1723 Depart at 9:56pm from Las Vegas (LAS) Fly for 2h 17m Arrive at 12:13am in Portland (PDX)

  • USD 143
    United Airlines
    8:05pm - 10:30pm
    Fri Jul 19th
    4h 25m
    Chicago (ORD) → Portland (PDX)
    Direct

    Fri Jul 19th 2024 United Airlines · UA 426 Depart at 8:05pm from Chicago (ORD) Fly for 4h 25m Arrive at 10:30pm in Portland (PDX)

  • USD 143
    United Airlines
    7:10am - 9:36am
    Fri Jul 19th
    4h 26m
    Chicago (ORD) → Portland (PDX)
    Direct

    Fri Jul 19th 2024 United Airlines · UA 2633 Depart at 7:10am from Chicago (ORD) Fly for 4h 26m Arrive at 9:36am in Portland (PDX)

  • USD 145
    Alaska Airlines
    8:00am - 10:20am
    Fri Jul 19th
    4h 20m
    Chicago (ORD) → Portland (PDX)
    Direct

    Fri Jul 19th 2024 Alaska Airlines · AS 325 Depart at 8:00am from Chicago (ORD) Fly for 4h 20m Arrive at 10:20am in Portland (PDX)

  • USD 148
    Alaska Airlines
    2:25pm - 4:45pm
    Thu Jul 18th
    4h 20m
    Chicago (ORD) → Portland (PDX)
    Direct

    Thu Jul 18th 2024 Alaska Airlines · AS 413 Depart at 2:25pm from Chicago (ORD) Fly for 4h 20m Arrive at 4:45pm in Portland (PDX)

  • USD 165
    Spirit Airlines
    6:19pm - 12:13am
    Thu Jul 18th
    7h 54m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Thu Jul 18th 2024 Spirit Airlines · NK 200 Depart at 6:19pm from Chicago (ORD) Fly for 3h 55m Arrive at 8:14pm in Las Vegas (LAS)

    Layover in Las Vegas for 1h 42m

    Thu Jul 18th 2024 Spirit Airlines · NK 1723 Depart at 9:56pm from Las Vegas (LAS) Fly for 2h 17m Arrive at 12:13am in Portland (PDX)

  • USD 186
    United Airlines
    7:10am - 9:36am
    Thu Jul 18th
    4h 26m
    Chicago (ORD) → Portland (PDX)
    Direct

    Thu Jul 18th 2024 United Airlines · UA 2633 Depart at 7:10am from Chicago (ORD) Fly for 4h 26m Arrive at 9:36am in Portland (PDX)

  • USD 199
    United Airlines
    8:05pm - 10:30pm
    Thu Jul 18th
    4h 25m
    Chicago (ORD) → Portland (PDX)
    Direct

    Thu Jul 18th 2024 United Airlines · UA 426 Depart at 8:05pm from Chicago (ORD) Fly for 4h 25m Arrive at 10:30pm in Portland (PDX)

  • USD 212
    Alaska Airlines
    8:00am - 10:20am
    Thu Jul 18th
    4h 20m
    Chicago (ORD) → Portland (PDX)
    Direct

    Thu Jul 18th 2024 Alaska Airlines · AS 325 Depart at 8:00am from Chicago (ORD) Fly for 4h 20m Arrive at 10:20am in Portland (PDX)

  • USD 222
    United Airlines
    4:20pm - 6:45pm
    Thu Jul 18th
    4h 25m
    Chicago (ORD) → Portland (PDX)
    Direct

    Thu Jul 18th 2024 United Airlines · UA 1865 Depart at 4:20pm from Chicago (ORD) Fly for 4h 25m Arrive at 6:45pm in Portland (PDX)

  • USD 237
    Alaska Airlines
    6:35am - 1:18pm
    Thu Jul 18th
    8h 43m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Thu Jul 18th 2024 Alaska Airlines · AS 457 Depart at 6:35am from Chicago (ORD) Fly for 4h 37m Arrive at 9:12am in San Francisco (SFO)

    Layover in San Francisco for 2h 24m

    Thu Jul 18th 2024 Alaska Airlines · AS 671 Depart at 11:36am from San Francisco (SFO) Fly for 1h 42m Arrive at 1:18pm in Portland (PDX)

  • USD 240
    United Airlines
    4:20pm - 6:45pm
    Fri Jul 19th
    4h 25m
    Chicago (ORD) → Portland (PDX)
    Direct

    Fri Jul 19th 2024 United Airlines · UA 1865 Depart at 4:20pm from Chicago (ORD) Fly for 4h 25m Arrive at 6:45pm in Portland (PDX)

  • USD 247
    United Airlines
    9:08pm - 7:39am
    Fri Jul 19th
    12h 31m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Fri Jul 19th 2024 United Airlines · UA 2144 Depart at 9:08pm from Chicago (ORD) Fly for 2h 44m Arrive at 10:52pm in Denver (DEN)

    Layover in Denver for 7h 8m

    Sat Jul 20th 2024 United Airlines · UA 1823 Depart at 6:00am from Denver (DEN) Fly for 2h 39m Arrive at 7:39am in Portland (PDX)

  • USD 247
    Alaska Airlines
    9:22pm - 9:41am
    Thu Jul 18th
    14h 19m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Thu Jul 18th 2024 Alaska Airlines · AS 901 Depart at 9:22pm from Chicago (ORD) Fly for 4h 37m Arrive at 11:59pm in Seattle (SEA)

    Layover in Seattle for 8h 46m

    Fri Jul 19th 2024 Alaska Airlines · AS 2184 Depart at 8:45am from Seattle (SEA) Fly for 0h 56m Arrive at 9:41am in Portland (PDX)

  • USD 248
    Alaska Airlines
    6:00am - 5:26pm
    Thu Jul 18th
    13h 26m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Thu Jul 18th 2024 Alaska Airlines · AS 333 Depart at 6:00am from Chicago (ORD) Fly for 4h 31m Arrive at 8:31am in Seattle (SEA)

    Layover in Seattle for 7h 58m

    Thu Jul 18th 2024 Alaska Airlines · AS 956 Depart at 4:29pm from Seattle (SEA) Fly for 0h 57m Arrive at 5:26pm in Portland (PDX)

  • USD 253
    Alaska Airlines
    6:35am - 1:18pm
    Fri Jul 19th
    8h 43m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Fri Jul 19th 2024 Alaska Airlines · AS 457 Depart at 6:35am from Chicago (ORD) Fly for 4h 37m Arrive at 9:12am in San Francisco (SFO)

    Layover in San Francisco for 2h 24m

    Fri Jul 19th 2024 Alaska Airlines · AS 671 Depart at 11:36am from San Francisco (SFO) Fly for 1h 42m Arrive at 1:18pm in Portland (PDX)

  • USD 263
    Alaska Airlines
    6:35am - 3:57pm
    Thu Jul 18th
    11h 22m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Thu Jul 18th 2024 Alaska Airlines · AS 457 Depart at 6:35am from Chicago (ORD) Fly for 4h 37m Arrive at 9:12am in San Francisco (SFO)

    Layover in San Francisco for 5h 3m

    Thu Jul 18th 2024 Alaska Airlines · AS 1244 Depart at 2:15pm from San Francisco (SFO) Fly for 1h 42m Arrive at 3:57pm in Portland (PDX)

  • USD 264
    Alaska Airlines
    6:00am - 12:18pm
    Thu Jul 18th
    8h 18m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Thu Jul 18th 2024 Alaska Airlines · AS 333 Depart at 6:00am from Chicago (ORD) Fly for 4h 31m Arrive at 8:31am in Seattle (SEA)

    Layover in Seattle for 2h 49m

    Thu Jul 18th 2024 Alaska Airlines · AS 1039 Depart at 11:20am from Seattle (SEA) Fly for 0h 58m Arrive at 12:18pm in Portland (PDX)

  • USD 267
    United Airlines
    12:45pm - 3:11pm
    Fri Jul 19th
    4h 26m
    Chicago (ORD) → Portland (PDX)
    Direct

    Fri Jul 19th 2024 United Airlines · UA 1946 Depart at 12:45pm from Chicago (ORD) Fly for 4h 26m Arrive at 3:11pm in Portland (PDX)

  • USD 271
    United Airlines
    9:16am - 11:44am
    Fri Jul 19th
    4h 28m
    Chicago (ORD) → Portland (PDX)
    Direct

    Fri Jul 19th 2024 United Airlines · UA 1799 Depart at 9:16am from Chicago (ORD) Fly for 4h 28m Arrive at 11:44am in Portland (PDX)

  • USD 273
    United Airlines
    6:15pm - 10:41pm
    Fri Jul 19th
    6h 26m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Fri Jul 19th 2024 United Airlines · UA 767 Depart at 6:15pm from Chicago (ORD) Fly for 2h 46m Arrive at 8:01pm in Denver (DEN)

    Layover in Denver for 0h 59m

    Fri Jul 19th 2024 United Airlines · UA 1325 Depart at 9:00pm from Denver (DEN) Fly for 2h 41m Arrive at 10:41pm in Portland (PDX)

  • USD 280
    Alaska Airlines
    6:20pm - 11:41pm
    Fri Jul 19th
    7h 21m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Fri Jul 19th 2024 Alaska Airlines · AS 597 Depart at 6:20pm from Chicago (ORD) Fly for 4h 40m Arrive at 9:00pm in San Francisco (SFO)

    Layover in San Francisco for 0h 59m

    Fri Jul 19th 2024 Alaska Airlines · AS 556 Depart at 9:59pm from San Francisco (SFO) Fly for 1h 42m Arrive at 11:41pm in Portland (PDX)

  • USD 283
    United Airlines
    12:45pm - 3:11pm
    Thu Jul 18th
    4h 26m
    Chicago (ORD) → Portland (PDX)
    Direct

    Thu Jul 18th 2024 United Airlines · UA 1946 Depart at 12:45pm from Chicago (ORD) Fly for 4h 26m Arrive at 3:11pm in Portland (PDX)

  • USD 297
    United Airlines
    5:16am - 9:34am
    Thu Jul 18th
    6h 18m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Thu Jul 18th 2024 United Airlines · UA 2666 Depart at 5:16am from Chicago (ORD) Fly for 2h 37m Arrive at 6:53am in Denver (DEN)

    Layover in Denver for 1h 2m

    Thu Jul 18th 2024 United Airlines · UA 1247 Depart at 7:55am from Denver (DEN) Fly for 2h 39m Arrive at 9:34am in Portland (PDX)

  • USD 306
    Alaska Airlines
    6:00am - 10:56am
    Thu Jul 18th
    6h 56m
    Chicago (ORD) → Portland (PDX)
    1 Stop

    Thu Jul 18th 2024 Alaska Airlines · AS 333 Depart at 6:00am from Chicago (ORD) Fly for 4h 31m Arrive at 8:31am in Seattle (SEA)

    Layover in Seattle for 1h 29m

    Thu Jul 18th 2024 Alaska Airlines · AS 2183 Depart at 10:00am from Seattle (SEA) Fly for 0h 56m Arrive at 10:56am in Portland (PDX)

  • USD 316
    United Airlines
    9:16am - 11:44am
    Thu Jul 18th
    4h 28m
    Chicago (ORD) → Portland (PDX)
    Direct

    Thu Jul 18th 2024 United Airlines · UA 1799 Depart at 9:16am from Chicago (ORD) Fly for 4h 28m Arrive at 11:44am in Portland (PDX)

  • USD 320
    Alaska Airlines
    2:25pm - 4:45pm
    Fri Jul 19th
    4h 20m
    Chicago (ORD) → Portland (PDX)
    Direct

    Fri Jul 19th 2024 Alaska Airlines · AS 413 Depart at 2:25pm from Chicago (ORD) Fly for 4h 20m Arrive at 4:45pm 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 (CHI 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