$150 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).

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
• Alaska Airlines: offers extra legroom; offers free seat selection

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

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

• United Airlines
• American Airlines
• Southwest
• Alaska Airlines

Flights from Portland to Chicago usually depart from Portland (PDX) 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 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.

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

• Economy Class
• Premium Economy Class
• Business Class
• First Class

Prices vary by airline.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $235 round-trip via Denver Intl (DEN), compared to $372 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:

• Denver Intl (DEN) - 46% of one-stop connections
• Seattle/Tacoma Intl (SEA) - 17% of one-stop connections
• Minneapolis St Paul (MSP) - 14% of one-stop connections
• San Diego (SAN) - 5% 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 15% on the Portland to Chicago route. Wednesday is the cheapest departure day at $357 round-trip on average, while Sunday is the most expensive at $417, a difference of $60. 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 Portland to Chicago flights, with 50% of flights leaving in that window. Night departures account for 30%, afternoon flights for 20%, and evening 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 12:02 am and lands at 4:08 am
• Latest: departs at 11:59 pm and lands at 4:05 am.

The flight takes about 4h 06m.

Last-minute fares on this route - booked within 2 weeks of departure - run 54% above the route average of $371. Book 9 weeks before departure for the lowest fares.

A nonstop flight from Portland to Chicago takes 4h 06m, 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 $322 to $1,685. 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 $173, which is 21% below the typical average for this route.

Flying via Salt Lake City (SLC) gives the shortest average 1-stop total travel time at 6h 25m, compared with 6h 49m via Seattle/Tacoma Intl (SEA) and 7h 19m via Chicago O'Hare Intl (ORD).

Chicago is 2 hours ahead of Portland (Central Time vs Pacific 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 $302 to $471, with an average of $371 over the past 12 months. Anything below $302 counts as a good deal.

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

• • American Airlines
• • Alaska Airlines
• • JetBlue