$156 Find Cheap Flights from Chicago to Portland - Compare and Save

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.

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

• Economy Class
• First Class

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

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.

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.

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

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.

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

• American Airlines: 83% on time
• United Airlines: 80% on time
• Southwest: 80% on time

Overall, flights on this route are punctual 82% of the time on average.

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.

Morning is the busiest departure period on Chicago to Portland flights, with 40% of flights leaving in that window. Evening departures account for 40%, afternoon flights for 20%, and night flights for 0%.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $353 to $2,175. That means the highest observed fare was about 6x higher than the lowest one.

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

• American Airlines
• JetBlue

Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

One-way fares from Chicago to Portland are currently lower than usual. Average one-way flight prices are about $171, which is 27% below the typical average for this route.

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

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).

Morning flights have the fewest delays on this route, while night departures tend to have the most.

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, 18% of flights were delayed in the past 3 months, with delays averaging 2h 17m.

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

Yes. Flexible dates can save you up to 23% on flights from Chicago to Portland. Saturday is the cheapest departure day at $336 round-trip on average, while Sunday is the most expensive at $432, a difference of $96.

Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

3 airlines operate flights between Chicago and Portland. The airlines offering nonstop flights on this route include:

• United Airlines
• American Airlines
• Southwest

Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 4h 33m, 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.

Among airlines operating Chicago to Portland flights:

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

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

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

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

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