$134 Find Cheap Flights from Chicago to Portland - Compare and Save

Among airlines operating Chicago to Portland flights:

• United Airlines: offers extra legroom; offers free seat selection
• American Airlines: offers extra legroom; offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

3 airlines operate flights between Chicago and Portland. The airlines offering nonstop flights on this route include:
• United Airlines
• American Airlines
• Southwest

Flights from Chicago to Portland may depart from several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Flights usually arrive at Portland (PWM).

Here are some options for this route, based on selected ticket types and cabin classes:

• United Airlines: a cabin bag and a checked bag in Economy Class
• American Airlines: a cabin bag and a checked bag in Economy Class
• Southwest: a cabin bag in Economy Class class

Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

Two cabin classes are available on flights from Chicago to Portland:

• Economy Class
• Premium Economy Class

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $215 round-trip via New York John F Kennedy Intl (JFK), compared to $374 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

One-stop flights from Chicago to Portland most commonly connect through:

• Baltimore/Washington (BWI) - 23% of one-stop connections
• Detroit Metropolitan Wayne County (DTW) - 17% of one-stop connections
• New York John F Kennedy Intl (JFK) - 13% of one-stop connections
• Washington, D.C. Reagan-National (DCA) - 10% of one-stop connections

Baltimore/Washington (BWI) handles the largest share of one-stop connections on this route.

On the Chicago to Portland route, being flexible with your departure day can save you up to 23%. Saturday is the cheapest day at $336 round-trip on average, while Sunday is the most expensive at $432: a $96 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Chicago to Portland route, 19% of flights were delayed in the past 3 months, with delays averaging 2 hours 14 minutes.

Morning is the busiest departure period on Chicago to Portland flights, with 34% of flights leaving in that window. Evening departures account for 33%, afternoon flights for 17%, and night flights for 16%.

A nonstop flight from Chicago to Portland takes 2h 35m, covering 885 miles.

These are the earliest and latest flight times available from Chicago to Portland:

• Earliest: departs at 6:59 am and lands at 9:34 am
• Latest: departs at 8:00 pm and lands at 10:35 pm.

The flight takes about 2h 35m.

Last-minute fares on this route - booked within 2 weeks of departure - run 27% above the route average of $373. Book 7 weeks before departure for the lowest fares.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $297 to $2,072. That means the highest observed fare was about 7x higher than the lowest one.

One-way fares from Chicago to Portland are currently lower than usual. Average one-way flight prices are about $146, which is 38% below the typical average for this route.

Southwest is slightly above the route average for timely arrivals, while American Airlines has a lower on-time arrival rate. On-time arrival rates on Chicago to Portland flights are:

• Southwest: 85% on time
• American Airlines: 83% on time
• United Airlines: 79% on time

Overall, flights on this route are on time 81% of the time on average.

Morning flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 4h 34m, compared with 4h 34m via New York LaGuardia (LGA) and 4h 46m via Philadelphia (PHL).

Portland is 1 hour ahead of Chicago (Eastern Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

Portland Airport (PWM) hosts 5 major car rental companies, with daily rates starting from around $24 for economy cars. Top options include:
· Dollar
· Budget
· Alamo
· Hertz
· Movly

Round-trip flights from Chicago to Portland range from $299 to $465, with an average of $373 over the past 12 months. Anything below $299 counts as a good deal.

Two airlines offer in-flight Wi-Fi on Chicago to Portland flights:

• • American Airlines
• • JetBlue