Cheap flights from Portland to Chicago
Fares from $181 in November 2026. Compare every month below, then book with the site you like.
Search Portland → Chicago flightsCheapest Portland to Chicago fares by month
Lowest price per person found in recent searches. Prices change often and are checked when you book.
- November 2026Nov 10 · one way · Frontier · 1 stop$181See deal
Portland to Chicago at a glance
- Distance1,735 miles
- Nonstop flight timeabout 4h 15m
- Cheapest monthNovember 2026
- Airport codesPDX → CHI
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Frequently asked questions
- How much is a flight from Portland to Chicago?
- The cheapest fare we found recently is $181 per person, departing Nov 10 on Frontier. Prices change daily, so search your dates to see today's fares.
- What is the cheapest month to fly from Portland to Chicago?
- November 2026 is currently the cheapest month, from $181.
- Are there direct flights from Portland to Chicago?
- The cheapest fares we found recently have at least one stop. Nonstop flights may still exist at a higher price; tick "Direct only" in the search to check.
- Which airlines fly from Portland to Chicago?
- The cheapest recent fares on this route were on Frontier.
- How long is the flight from Portland to Chicago?
- Portland and Chicago are about 1,735 miles apart, so a nonstop flight takes roughly 4h 15m. Flights with a stop take longer, depending on the connection.
- How do I find the cheapest flight from Portland to Chicago?
- Search your dates on Gotoesy. We list fares from several booking sites sorted cheapest first, show nearby dates when your day has no saved fare, and send you straight to the seller to book.
More flights from Portland
- Portland to New York
- Portland to Los Angeles
- Portland to Miami
- Portland to Orlando
- Portland to Las Vegas
- Portland to San Francisco
- Portland to Washington, D.C.
- Portland to Boston
- Portland to Atlanta
- Portland to Dallas
- Portland to Houston
- Portland to Seattle