Cheap Flights from Portland to Chicago
No deal from Portland to Chicago has cleared our price bar yet. What we have seen on the route is below.
Across 4 months of observations from Portland to Chicago, the lowest round-trip fare we recorded was $166, in August. The typical fare was $286. August was the cheapest month we saw and July the dearest.
The most recent price we saw on this route was $310 on Frontier and United, seen Oct 16. It is an unverified observation and may have changed.
See every deal <a href="/from/portland">from Portland</a>, <a href="/to/chicago">to Chicago</a>, or the return direction <a href="/from/chicago/to/portland">Chicago to Portland</a>.
Latest price we saw: Portland to Chicago
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 |
|---|---|---|---|---|---|---|
| Portland (PDX) to Chicago (ORD) | $310 | 8.9¢ | Feb 22 – Mar 2 | Frontier and United | Oct 16 | Check price |
Price history: Portland to Chicago
What we observed by month, from our signals database. Unverified observations, not bookable prices.
| Month | Low | Typical | Sightings |
|---|---|---|---|
| Oct 2026 | $234 | $259 | 60 |
| Sep 2026 | $244 | $301 | 90 |
| Aug 2026 | $166 | $307 | 130 |
| Jul 2026 | $278 | $278 | 1 |
Frequently asked questions
How many flight deals from Portland to Chicago are on Sparkflights right now?
There are 0 verified deals from Portland to Chicago on the board right now. The list refreshes hourly.
What is the lowest price ever seen from Portland to Chicago?
The lowest fare we've recorded from Portland to Chicago is $166, based on 281 price observations over 4 months.
How much does a flight from Portland to Chicago cost?
The typical round-trip fare we observed from Portland to Chicago is $286, against a recorded low of $166. These are observations, not quotes.
When is the cheapest month to fly Portland to Chicago?
August was the cheapest month we observed from Portland to Chicago and July the dearest, over 4 months of data.
What is the current price from Portland to Chicago?
The most recent fare our sweep saw from Portland to Chicago is $310, on Oct 16. It is an unverified observation rather than a verified deal, so check it before booking.