$163 Find Cheap Flights from Chicago Midway Airport to Portland - Compare and Save

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 (PWM).

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

• Southwest: a cabin bag in Economy Class class

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

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

• Economy Class
• First Class

On this route, nonstop and layover fares are close on average, with nonstop at $389 round-trip and layover options via Baltimore/Washington (BWI) at $379.

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 Embraer 175 family is used most often on this route, operated mainly by American Airlines. Other aircraft seen on the route include Boeing 737 MAX 8 variants.

Most connecting flights from Chicago Midway Airport to Portland pass through Baltimore/Washington (BWI), which handles 100% of one-stop traffic on this route. Other layover airports each see under 5%.

Yes. Being flexible with your travel dates can save you up to 52% on the Chicago Midway Airport to Portland route. Friday is the cheapest departure day at $289 round-trip on average, while Sunday is the most expensive at $591, a difference of $302. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Chicago Midway Airport to Portland route, 19% of flights were delayed in the past 3 months, with delays averaging 2 hours 12 minutes.

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

• Earliest: departs at 7:45 am and lands at 10:02 am
• Latest: departs at 7:50 pm and lands at 10:07 pm.

The flight takes about 2h 17m.

A nonstop flight from Chicago Midway Airport to Portland takes 2h 17m, covering 892 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 $302 to $2,565. That means the highest observed fare was about 8x 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 $177, which is 23% below the typical average for this route.

Southwest is the only airline operating Chicago Midway Airport to Portland flights. 81% of its flights are on time.

Morning flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

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

Portland Airport (PWM) hosts 5 major car rental companies, with daily rates starting from around $24 for economy cars. Top options include:
• Dollar
• Budget
• Alamo
• Hertz
• Movly

Round-trip flights from Chicago Midway Airport to Portland range from $289 to $434, with an average of $389 over the past 12 months. Anything below $289 counts as a good deal.