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How to get from Portland to Chicago

No nonstop flights. The fastest way is via Pittsburgh: about 6h 53m including the connection. Other options: via Washington, Philadelphia and New York. Two tickets from $208.

Flights from Portland to Chicago

Pick a departure date to see flights and seller prices

We search agencies and airlines for your day: nonstop and connecting flights, baggage, departure and arrival times.

Filters

Best fares from Portland to Chicago

Lowest one-way prices found by recent searches for the next 120 days; press a card to search that date

Cheapest one-way $192 21 November 2026, with a connection Cheapest nonstop $228 21 November 2026, UA Cheapest weekend departure $192 Sat, 21 November 2026 Cheapest month November 2026 tickets from $192

Where to connect

Options with one connection, fastest first

fastest, via Pittsburgh
6h 53m
two tickets, via New York
$208
connection options
4
straight-line distance
885 mi (1,425 km)
fastest
Via Pittsburgh
6h 53m
with the connection
Portland to Pittsburgh flight 1h 58m
Connection of about 3h
Pittsburgh to Chicago flight 1h 55m
Via Washington
7h 18m
with the connection
Portland to Washington flight 1h 59m
Connection of about 3h Arrival: Baltimore/Wash International Thurgood Marshall, Ronald Reagan National, Washington Dulles International. Departure to Chicago: Baltimore/Wash International Thurgood Marshall, Ronald Reagan National, Washington Dulles International.
Washington to Chicago flight 2h 19m
Via Philadelphia
7h 24m
with the connection
Portland to Philadelphia flight 1h 48m
Connection of about 3h
Philadelphia to Chicago flight 2h 36m
Via New York
7h 26m
with the connection
Portland to New York flight 1h 36m
Connection of about 3h Arrival: John F. Kennedy International, LaGuardia, Newark Liberty International. Departure to Chicago: LaGuardia, Newark Liberty International.
New York to Chicago flight 2h 50m
two ticketsfrom $208

One ticket or two

How the options are calculated and what to keep in mind at the connection

Flight times come from the nonstop schedule (estimated from the distance where there is no schedule), with 3h allowed for the connection. The price of an option is the sum of the lowest known fares for each leg; their dates may not match, so treat it as a guide. The search shows tickets for your dates, including connections on a single ticket.

When to visit Chicago

Weather by month

Best time to visit: May, June, July, August, September and October, +18° to +27° by day. In November it is +10° by day and +2° at night, with 7 rainy days.

Jan
0° −7° 10 days
Feb
+2° −6° 7 days
Mar
+9° 0° 12 days
Apr
+14° +5° 13 days
May
+19° +10° 11 days
Jun
+27° +17° 9 days
Jul
+27° +19° 12 days
Aug
+27° +19° 10 days
Sep
+24° +16° 7 days
Oct
+18° +10° 11 days
Nov
+10° +2° 7 days
Dec
+4° −3° 10 days

Daytime and night temperatures in °C, rainy days. Months with the most comfortable weather are in green. Long-term averages.

Nearest nonstop flights

The closest you can get without a connection

Frequently asked questions

Is there a nonstop flight from Portland to Chicago?
There are no nonstop flights in the schedule. You will need a connection, the fastest is via Pittsburgh.
What is the fastest way to fly from Portland to Chicago?
Via Pittsburgh: 1h 58m to the connection, 1h 55m after it, about 6h 53m in total with 3h for the connection.
How much does a flight from Portland to Chicago with a connection cost?
Two nonstop tickets via New York from $208. This is the sum of the lowest known prices for each leg, and their dates may not match.
Which cities can you connect in between Portland and Chicago?
Pittsburgh (6h 53m total), Washington (7h 18m total), Philadelphia (7h 24m total) and New York (7h 26m total).
How far is Chicago from Portland?
885 mi (1,425 km) in a straight line between the cities.
How much time should I allow for the connection?
The options allow 3h. On a single ticket the carrier is responsible for the connection; on separate tickets you set the margin yourself, allowing time to collect and re-check your bags.