$135 Find Cheap Flights from Portland to Chicago - Compare and Save

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

• Earliest: departs at 6:30 am and lands at 9:38 am
• Latest: departs at 6:00 pm and lands at 9:08 pm.

The flight takes about 3h 08m.

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

• Economy Class
• First Class

A nonstop flight from Portland to Chicago takes 3h 08m, 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 Portland to Chicago range from $313 to $464, with an average of $380 over the past 12 months. Anything below $313 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 25% above the $380 route average. Book 26 weeks before departure for the lowest fares.

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 $382 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.

Morning is the busiest departure period on Portland to Chicago flights, with 50% of flights leaving in that window. Afternoon departures account for 50%, evening flights for 0%, 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 $344 to $2,220. That means the highest observed fare was about 6x higher than the lowest one.

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

One-way fares from Portland to Chicago are currently lower than usual. Average one-way flight prices are about $150, which is 37% below the typical average for this route.

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 averaging $64:

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

Near Chicago Midway Airport (MDW) — daily rates averaging $84:

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

Near Chicago Greater Rockford Airport (RFD) — daily rates averaging $81:

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

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).

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

• Baltimore/Washington (BWI) - 24% of one-stop connections
• Washington, D.C. Reagan-National (DCA) - 24% of one-stop connections
• New York John F Kennedy Intl (JFK) - 13% of one-stop connections
• Detroit Metropolitan Wayne County (DTW) - 11% of one-stop connections

Yes. Flexible dates can save you up to 30% on flights from Portland to Chicago. Saturday is the cheapest departure day at $349 round-trip on average, while Sunday is the most expensive at $497, a difference of $148.

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

3 airlines operate flights between Portland and Chicago. 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 22m, compared with 5h via Washington, D.C. Reagan-National (DCA) and 5h 11m via New York LaGuardia (LGA).

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

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

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.

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 always check the fare details before booking.