$179 Find Cheap Flights from Chicago to Portland - Compare and Save

Traveling with your pet out of Chicago is a breeze as both O’Hare International Airport and Midway International Airport are pet friendly. The pet relief stations in O’Hare International Airport are located at Terminals 1, 2, 3, 5, and the Multi-Modal Facility. Midway International Airport also has pet relief stations located both outside and inside the terminal. The pet relief station located inside the terminal is just past the Concourse A security checkpoint and features artificial turf and an automatic flushing system for easy cleanup.

If you may require accessibility services, you should consider flying out of Midway International Airport. The airport is less crowded than O’Hare International Airport, meaning that most areas and facilities will be available for use. The airport also provides a multitude of accessibility features, such as wheelchair-accessible restrooms and elevators with raised numerals and Braille. The airport also provides parking spots for people with disabilities, which are wide enough for ramp and lift access.

The easiest and most convenient way to get from Portland International Airport to downtown Portland is by using the Max Light rail Red Line, which will take you less than 40min. The last train leaves the airport at 11:50 pm. You can also decide to use private means, such as taxicabs, ridesharing services, or car rental from any of the several car rental companies that operate from within the airport.

Getting to O’Hare International Airport from downtown Chicago is made easy by the city’s intricate public transportation system. You can conveniently use the CTA L Trains to get from the city to the airport, as well as the airport shuttle services that transport passengers to the airport. Additionally, the airport has multiple parking options that allow you to drive to the airport and leave your vehicle for either a short or a long time.

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
• Alaska 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.

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

• United Airlines
• American Airlines
• Southwest
• Alaska Airlines

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 (PDX).

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
• Alaska Airlines: a cabin bag and a checked bag in Economy Class

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

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

• Economy Class
• Business Class
• First Class

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $231 round-trip via Las Vegas Harry Reid Intl (LAS), compared to $356 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:

• Denver Intl (DEN) - 70% of one-stop connections
• Chicago O'Hare Intl (ORD) - 16% of one-stop connections
• Las Vegas Harry Reid Intl (LAS) - 6% of one-stop connections
• Minneapolis St Paul (MSP) - 4% of one-stop connections

Denver Intl (DEN) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 18% on the Chicago to Portland route. Tuesday is the cheapest departure day at $339 round-trip on average, while Sunday is the most expensive at $409, a difference of $70. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Morning is the busiest departure period on Chicago to Portland flights, with 34% of flights leaving in that window. Afternoon departures account for 33%, evening flights for 22%, and night flights for 11%.

Some of the most popular sights in Portland are Moda Center, Oregon Convention Center and OHSU Center for Health and Healing. These are among the most viewed places in Portland on KAYAK.

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

• Earliest: departs at 7:00 am and lands at 11:37 am
• Latest: departs at 10:55 pm and lands at 3:32 am.

The flight takes about 4h 37m.

Last-minute fares on this route - booked within 2 weeks of departure - run 57% above the route average of $354. Book 10 weeks before departure for the lowest fares.

A nonstop flight from Chicago to Portland takes 4h 37m, covering 1,749 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 $318 to $1,665. That means the highest observed fare was about 5x higher than the lowest one.

One-way fares from Chicago to Portland are currently lower than usual. Average one-way flight prices are about $179, which is 18% below the typical average for this route.

Flying via Minneapolis St Paul (MSP) gives the shortest average 1-stop total travel time at 6h 22m, compared with 6h 23m via Seattle/Tacoma Intl (SEA) and 7h 55m via Chicago O'Hare Intl (ORD).

Portland is 2 hours behind Chicago (Pacific Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

Portland Airport (PDX) hosts 5 major car rental companies, with daily rates starting from around $24 for economy cars. Top options include:
• Thrifty
• Dollar
• Hertz
• Sixt
• Payless

Round-trip flights from Chicago to Portland range from $288 to $454, with an average of $354 over the past 12 months. Anything below $288 counts as a good deal.

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

• • American Airlines
• • Alaska Airlines
• • JetBlue