$155 Find Cheap Flights from Portland to Chicago Midway Airport - Compare and Save

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.

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

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.

Round-trip flights from Portland to Chicago Midway Airport range from $351 to $436, with an average of $397 over the past 12 months. Anything below $351 counts as a good deal.

On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $397 round-trip, compared to $426 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 Embraer 175 family is used most often on this route, operated mainly by American Airlines. Other aircraft seen on the route include Embraer 175 (Enhanced Winglets) variants.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $355 to $2,444. That means the highest observed fare was about 7x 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 $157, which is 33% below the typical average for this route.

Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates averaging $84 for economy cars. Top options include:

• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

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

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

Yes. Flexible dates can save you up to 31% on flights from Portland to Chicago Midway Airport. Friday is the cheapest departure day at $377 round-trip on average, while Sunday is the most expensive at $545, a difference of $168.

KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Only Southwest operates flights between Portland and Chicago Midway Airport.

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.

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

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.

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 always check the fare details before booking.