$113 Find Cheap Flights from Portland to Chicago - Compare and Save

Among airlines operating Portland to Chicago flights:

• United Airlines: offers extra legroom; 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.

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

• United Airlines
• American Airlines
• Southwest

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

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 Portland to Chicago:

• Economy Class
• First Class

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $253 round-trip via Chicago O'Hare Intl (ORD), compared to $366 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 Portland to Chicago most commonly connect through:

• Washington, D.C. Reagan-National (DCA) - 26% of one-stop connections
• Baltimore/Washington (BWI) - 22% of one-stop connections
• Detroit Metropolitan Wayne County (DTW) - 13% of one-stop connections
• New York John F Kennedy Intl (JFK) - 11% of one-stop connections

Washington, D.C. Reagan-National (DCA) handles the largest share of one-stop connections on this route.

On the Portland to Chicago route, being flexible with your departure day can save you up to 33%. Saturday is the cheapest day at $334 round-trip on average, while Sunday is the most expensive at $492: a $158 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

Morning is the busiest departure period on Portland to Chicago flights, with 60% of flights leaving in that window. Afternoon departures account for 20%, evening flights for 20%, and night flights for 0%.

Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago on KAYAK.

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

• Earliest: departs at 6:00 am and lands at 9:01 am
• Latest: departs at 6:00 pm and lands at 9:01 pm.

The flight takes about 3h 01m.

Last-minute fares on this route - booked within 2 weeks of departure - run 26% above the route average of $366. Book 26 weeks before departure for the lowest fares.

A nonstop flight from Portland to Chicago takes 3h 01m, 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.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $304 to $1,478. That means the highest observed fare was about 5x higher than the lowest one.

One-way fares from Portland to Chicago are currently lower than usual. Average one-way flight prices are about $170, which is 28% below the typical average for this route.

Flying via Philadelphia (PHL) gives the shortest average 1-stop total travel time at 4h 37m, compared with 4h 41m via Detroit Metropolitan Wayne County (DTW) and 5h 08m via Washington, D.C. Reagan-National (DCA).

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

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

• Routes Car & Truck Rentals
• Europcar
• Hertz
• Dollar
• Ace

Near Chicago Midway Airport (MDW) — daily rates from around $32:

• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

• Alamo
• Enterprise Rent-A-Car
• Budget
• Avis
• National

Round-trip flights from Portland to Chicago range from $291 to $446, with an average of $366 over the past 12 months. Anything below $291 counts as a good deal.

American Airlines is the only airline on the Portland to Chicago route offering in-flight Wi-Fi. Pricing depends on fare class.