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Cheap flights from Chicago to Portland

One-way from $150, found by travellers in the last 7 days. The live price is checked when you book.

Departure
Return
Prices for nearby dates
Mon, Feb 1Any priceTue, Feb 2Any priceWed, Feb 3Any priceThu, Feb 4$150Fri, Feb 5Any priceSat, Feb 6Any priceSun, Feb 7Any priceMon, Feb 8Any price

Cheapest one-way tickets

Recent finds on different dates, for 1 adult. Booking opens on Aviasales, which shows baggage, fare rules and the live price.

Cheapest
$150
Alaska Airlines, flight AS 325Found today, 1 adult
Check live price
2:10pmChicagoThu, Feb 4
Travel time 4h 40m, nonstopORDPDX
4:50pmPortlandThu, Feb 4
$173
Frontier Airlines, flight F9 1483Found 7 days ago, 1 adult
Check live price
6:30amChicagoTue, Nov 3
Travel time 5h 53m, 1 stopORDPDX
10:23amPortlandTue, Nov 3
$189
Frontier Airlines, flight F9 1483Found 3 days ago, 1 adult
Check live price
6:30amChicagoTue, Oct 27
Travel time 5h 53m, 1 stopORDPDX
10:23amPortlandTue, Oct 27
$196
Alaska Airlines, flight AS 325Found today, 1 adult
Check live price
2:03pmChicagoSun, Feb 21
Travel time 4h 34m, nonstopORDPDX
4:37pmPortlandSun, Feb 21
$241
Alaska Airlines, flight AS 325Found today, 1 adult
Check live price
2:16pmChicagoTue, Aug 10
Travel time 4h 34m, nonstopORDPDX
4:50pmPortlandTue, Aug 10

Plan the rest of the trip

  • Mobile data in United StatesTravel eSIM from $4, installed before you fly.
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  • Getting from the airportTransfers and car hire in Portland, booked ahead at a fixed price.
    See options
  • Things to do in PortlandPopular tours from $30 per person.
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  • Flight delayed?Delayed or cancelled? See which passenger rights cover this route.
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Price calendar

The lowest one-way fare found for each day over the next 60 days. A dash means no recent fare; you can still pick that day.

October 2026

MoTuWeThFrSaSu12345678910111213141516171819202122232425–26–27$18928$25629–30–31–

November 2026

MoTuWeThFrSaSu1–2$2723$1734$2515–6–7–8–9–10–11–12–13–14–15–16–17–18–19–20–21–22–23–24–25–26–27–28–29–30–

December 2026

MoTuWeThFrSaSu1–2–3–4–5–6–7–8–9–10–11–12–13–14–15–16–17–18–19–20–21–22–23–2425262728293031
$173 or lessGreen: the cheapest fifth of fares on this route. Lowest in these 60 days: Nov 3, $173.

Lowest fares by month

In the fares found this week, February 2027 has the lowest: from $150 one-way, against $241 in August 2027. Pick a month to see its cheapest date.

  1. Oct$189
  2. Nov$173
  3. Decno fares yet
  4. Janno fares yet
  5. Feb$150
  6. Marno fares yet
  7. Aprno fares yet
  8. Mayno fares yet
  9. Junno fares yet
  10. Julno fares yet
  11. Aug$241
  12. Sepno fares yet
$0$100$200$300OctNovDecJan$150FebMarAprMayJunJulAugSep
Show as a table
MonthCheapest one-wayDateStops
October$189Tue, Oct 271 stop
November$173Tue, Nov 31 stop
December—
January 2027—
February 2027$150Thu, Feb 4Nonstop
March 2027—
April 2027—
May 2027—
June 2027—
July 2027—
August 2027$241Tue, Aug 10Nonstop
September 2027—

Questions travellers ask

What is the cheapest month to fly from Chicago to Portland?

In the fares found this week, February 2027 has the lowest: from $150 one-way, against $241 in August 2027.

Are there direct flights from Chicago to Portland?

Yes. Recent fares include nonstop flights with Alaska Airlines and Southwest Airlines.

How long is the flight from Chicago to Portland?

A nonstop flight takes about 4h 30m. The distance is 1,734 mi.

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