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

Among airlines operating Chicago Midway Airport to Portland flights:

• Southwest: offers free seat selection

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

Only Southwest operates flights between Chicago Midway Airport and Portland.

Flights from Chicago Midway Airport to Portland usually depart from Chicago Midway (MDW) and arrive at Portland (PDX).

Here are some options for this route, based on selected ticket types and cabin classes:

• 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.

Only Economy Class is available on flights from Chicago Midway Airport to Portland.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $297 round-trip via Minneapolis St Paul (MSP), compared to $346 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

The Boeing 737-800 family is used most often on this route, operated mainly by United Airlines and American Airlines. Other aircraft seen on the route include Boeing 737 MAX 8 variants.

Connecting flights from Chicago Midway Airport to Portland most commonly pass through:

• Denver Intl (DEN) - 80% of one-stop connections
• Minneapolis St Paul (MSP) - 20% of one-stop connections
Together, these airports account for 100% of one-stop bookings on this route.

Yes. Being flexible with your travel dates can save you up to 31% on the Chicago Midway Airport to Portland route. Friday is the cheapest departure day at $314 round-trip on average, while Sunday is the most expensive at $450, a difference of $136. 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 Midway Airport to Portland flights, with 50% of flights leaving in that window. Evening departures account for 50%, afternoon flights for 0%, and night flights for 0%.

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 Midway Airport to Portland:

• Earliest: departs at 9:35 am and lands at 2:05 pm
• Latest: departs at 10:55 pm and lands at 3:25 am.

The flight takes about 4h 30m.

A nonstop flight from Chicago Midway Airport to Portland takes 4h 30m, covering 1,746 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 $1,891. That means the highest observed fare was about 6x higher than the lowest one.

One-way fares from Chicago Midway Airport to Portland are currently lower than usual. Average one-way flight prices are about $181, which is 16% below the typical average for this route.

Flying via Minneapolis St Paul (MSP) gives the shortest average 1-stop total travel time at 7h 36m, compared with 10h 09m via Denver Intl (DEN).

Portland is 2 hours behind Chicago Midway Airport (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 Midway Airport to Portland range from $296 to $470, with an average of $350 over the past 12 months. Anything below $296 counts as a good deal.