Cheap Flights from Chicago to Portland
No deal from Chicago to Portland has cleared our price bar yet. What we have seen on the route is below.
Across 3 months of observations from Chicago to Portland, the lowest round-trip fare we recorded was $184, in August. The typical fare was $316. August was the cheapest month we saw and September the dearest.
The most recent price we saw on this route was $319 on Frontier, seen Oct 17. It is an unverified observation and may have changed.
See every deal <a href="/from/chicago">from Chicago</a>, <a href="/to/portland">to Portland</a>, or the return direction <a href="/from/portland/to/chicago">Portland to Chicago</a>.
Latest price we saw: Chicago to Portland
The most recent round-trip fare our sweep found on this route. It is not verified and may have changed since the date shown.
| From | Price | Per mile | Travel dates | Airline | Seen | Check price |
|---|---|---|---|---|---|---|
| Chicago (ORD) to Portland (PDX) | $319 | 9.2¢ | Nov 12 – Nov 21 | Frontier | Oct 17 | Check price |
Price history: Chicago to Portland
What we observed by month, from our signals database. Unverified observations, not bookable prices.
| Month | Low | Typical | Sightings |
|---|---|---|---|
| Oct 2026 | $222 | $287 | 18 |
| Sep 2026 | $250 | $374 | 112 |
| Aug 2026 | $184 | $288 | 138 |
Frequently asked questions
How many flight deals from Chicago to Portland are on Sparkflights right now?
There are 0 verified deals from Chicago to Portland on the board right now. The list refreshes hourly.
What is the lowest price ever seen from Chicago to Portland?
The lowest fare we've recorded from Chicago to Portland is $184, based on 268 price observations over 3 months.
How much does a flight from Chicago to Portland cost?
The typical round-trip fare we observed from Chicago to Portland is $316, against a recorded low of $184. These are observations, not quotes.
When is the cheapest month to fly Chicago to Portland?
August was the cheapest month we observed from Chicago to Portland and September the dearest, over 3 months of data.
What is the current price from Chicago to Portland?
The most recent fare our sweep saw from Chicago to Portland is $319, on Oct 17. It is an unverified observation rather than a verified deal, so check it before booking.