$121 Find Cheap Flights from Pittsburgh to Chicago Midway Airport - Compare and Save

Among airlines operating Pittsburgh 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 Pittsburgh and Chicago Midway Airport.

Flights from Pittsburgh to Chicago Midway Airport usually depart from Pittsburgh (PIT) 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 Pittsburgh to Chicago Midway Airport.

On this route, nonstop and layover fares are close on average, with nonstop at $334 round-trip and layover options via Detroit Metropolitan Wayne County (DTW) at $333.

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 Airbus A320-100/200 family is used most often on this route, operated mainly by United Airlines and American Airlines. Other aircraft seen on the route include Airbus A319 variants.

Most connecting flights from Pittsburgh to Chicago Midway Airport pass through Detroit Metropolitan Wayne County (DTW), 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 51% on the Pittsburgh to Chicago Midway Airport route. Wednesday is the cheapest departure day at $240 round-trip on average, while Sunday is the most expensive at $488, a difference of $248. 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 Pittsburgh to Chicago Midway Airport route, 16% of flights were delayed in the past 3 months, with delays averaging 1 hour 40 minutes.

Morning is the busiest departure period on Pittsburgh to Chicago Midway Airport flights, with 34% of flights leaving in that window. Afternoon departures account for 33%, evening flights for 33%, and night flights for 0%.

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 Pittsburgh to Chicago Midway Airport:

• Earliest: departs at 7:25 am and lands at 8:55 am
• Latest: departs at 9:15 pm and lands at 10:45 pm.

The flight takes about 1h 30m.

Last-minute fares on this route - booked within 2 weeks of departure - run 78% above the route average of $329. Book 25 weeks before departure for the lowest fares.

A nonstop flight from Pittsburgh to Chicago Midway Airport takes 1h 30m, covering 400 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 $247 to $744. That means the highest observed fare was about 3x higher than the lowest one.

One-way fares from Pittsburgh to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $130, which is 31% below the typical average for this route.

Southwest is the only airline operating Pittsburgh to Chicago Midway Airport flights. 84% of its flights are on time.

Night 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.

Chicago Midway Airport is 1 hour behind Pittsburgh (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 Pittsburgh to Chicago Midway Airport range from $226 to $462, with an average of $329 over the past 12 months. Anything below $226 counts as a good deal.