How to get from Chicago to Portland: connecting flights, about 6h 37m total

Flights from Chicago to Portland

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.

Best fares from Chicago to Portland

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

Cheapest one-way $203 14 December 2026, with a connection Cheapest nonstop $229 14 December 2026, AA Cheapest month December 2026 tickets from $203

Where to connect

Options with one connection, fastest first

fastest, via New York: 6h 37m
two tickets, via New York: $272
connection options: 3
straight-line distance: 885 mi (1,425 km)

fastest

Via New York

6h 37m

with the connection

Chicago to New York flight 2h 11m

Connection of about 3h Arrival: John F. Kennedy International, LaGuardia, Newark Liberty International. Departure to Portland: John F. Kennedy International, LaGuardia, Newark Liberty International.

New York to Portland flight 1h 26m

two ticketsfrom $272

Via Philadelphia

6h 39m

with the connection

Chicago to Philadelphia flight 2h 5m

Connection of about 3h

Philadelphia to Portland flight 1h 34m

two ticketsfrom $380

Via Indianapolis

8h 22m

with the connection

Chicago to Indianapolis flight 1h 11m

Connection of about 3h

Indianapolis to Portland flight 4h 11m

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.

Nearest nonstop flights

The closest you can get without a connection

From Chicago to cities closest to Portland

Chicago to Boston Boston: 97 mi (156 km) from Portland, flight 2h 26m from $143 Chicago to Providence Providence: 138 mi (222 km) from Portland, flight 2h 22m from $187 Chicago to Montreal Montreal: 205 mi (330 km) from Portland, flight 2h 22m from $145 Chicago to New York New York: 277 mi (446 km) from Portland, flight 2h 11m from $103 Chicago to Ottawa Ottawa: 292 mi (470 km) from Portland, flight 2h 18m from $360 Chicago to Philadelphia Philadelphia: 357 mi (575 km) from Portland, flight 2h 5m from $88

To Portland from cities closest to Chicago

Indianapolis to Portland Indianapolis: 165 mi (265 km) from Chicago, flight 4h 11m Atlanta to Portland Atlanta: 589 mi (948 km) from Chicago, flight 2h 33m Philadelphia to Portland Philadelphia: 664 mi (1,068 km) from Chicago, flight 1h 34m from $292 New York to Portland New York: 711 mi (1,144 km) from Chicago, flight 1h 26m from $128

Frequently asked questions

Is there a nonstop flight from Chicago to Portland?

There are no nonstop flights in the schedule. You will need a connection, the fastest is via New York.

What is the fastest way to fly from Chicago to Portland?

Via New York: 2h 11m to the connection, 1h 26m after it, about 6h 37m in total with 3h for the connection.

How much does a flight from Chicago to Portland with a connection cost?

Two nonstop tickets via New York from $272. 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 Chicago and Portland?

New York (6h 37m total), Philadelphia (6h 39m total) and Indianapolis (8h 22m total).

How far is Portland from Chicago?

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.