$164 Find Cheap Flights from Portland to Chicago - Compare and Save

Near the tunnels that connect the north and south terminals, PDX has long-term parking lots. Further away, PDX has an economy lot. This economy lot is less expensive and there is a 24h shuttle service for free that will take you to your terminal.

The USO lounge at PDX is before security on the mezzanine level. It is open Monday to Friday 9 am to 5 pm. The USO is closed on Saturday and Sunday. This lounge is available to active-duty military service members and their families. Local and transportation information is available here. Amenities at the lounge include TV, Xbox 30, Wi-Fi, computers, laptops, toiletries, free drinks, and lounge seating.

The two major airports in Chicago are Chicago O'Hare International Airport (ORD) and Midway International Airport (MDW). ORD is a hub for United Airlines and American Airlines and the airport has four terminals. Midway, a hub for Southwest Airlines, is much smaller, with just one terminal and three concourses.

United Airlines and Alaska Airlines operate non-stop flights from PDX into Chicago. All of these flights tend to land at ORD airport. Southwest operates non-stop flights from PDX that land at MDW. Alaska Airlines, Delta, Spirit, and United Airlines operate one stop flights from PDX to ORD. Some layover cities include Las Vegas (LAS), Seattle (SEA) and Denver (DEN). Delta operates one stop flights from PDX that land in MDW. These flights tend to stop at cities such as Atlanta (ATL) and Detroit (DTW).

In the last 5 days, the lowest price for a flight from Portland to Chicago was $164 for a one-way ticket and $319 for a round-trip.

Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

American Airlines, Alaska Airlines, JetBlue, and Delta offer inflight Wi-Fi service on the Portland to Chicago flight route.

The Boeing 737-800 is the aircraft model that flies most regularly on the Portland to Chicago flight route.

SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Portland and Chicago, with SkyTeam being the most commonly used for this route.

There are nonstop flights from Portland to Chicago on a daily basis.

The two airlines most popular with KAYAK users for flights from Portland to Chicago are Southwest and Alaska Airlines. With an average price for the route of $332 and an overall rating of 8.0, Southwest is the most popular choice. Alaska Airlines is also a great choice for the route, with an average price of $372 and an overall rating of 7.9.

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Portland to Chicago.

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Portland is likely to change within 7 days, so travelers know whether to wait or book now.

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Portland with another airline.

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Portland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.