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

Among airlines operating Portland to Chicago Midway Airport flights:

• Southwest: offers free seat selection

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

Only Southwest operates flights between Portland and Chicago Midway Airport.

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

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.

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

On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $397 round-trip, compared to $421 via a layover through Baltimore/Washington (BWI).

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

Most connecting flights from Portland to Chicago Midway Airport 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 35% on the Portland to Chicago Midway Airport route. Friday is the cheapest departure day at $359 round-trip on average, while Sunday is the most expensive at $545, a difference of $186. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

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

• Earliest: departs at 6:30 am and lands at 9:05 am
• Latest: departs at 6:00 pm and lands at 8:35 pm.

The flight takes about 2h 35m.

A nonstop flight from Portland to Chicago Midway Airport takes 2h 35m, 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 $337 to $1,478. That means the highest observed fare was about 4x higher than the lowest one.

One-way fares from Portland to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $179, which is 24% below the typical average for this route.

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

Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:
• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Round-trip flights from Portland to Chicago Midway Airport range from $349 to $441, with an average of $397 over the past 12 months. Anything below $349 counts as a good deal.