Cheap Flights from Pittsburgh International to Chicago Midway

Compare Pittsburgh International to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from Pittsburgh International Airport to Chicago Midway Airport

Looking for a cheap last-minute deal or the best return flight from Pittsburgh International Airport to Chicago Midway Airport? If you want to travel next month, return fares start from R 2,676. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Pittsburgh International to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Pittsburgh International to Chicago Midway flights are currently cheapest in April.

Direct flights from Pittsburgh International to Chicago Midway

Pittsburgh International to Chicago Midway: Alternative routes

Compare routes from Pittsburgh International to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Pittsburgh to Chicago: Flight information

The things to know before you go.
Cheapest flight foundR 1,170
Cheapest month to flyApril
Average flight time1 hr, 28 mins
Most popular airlineSouthwest Airlines
Average flights per week22

Finding cheap flights from Pittsburgh International to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Pittsburgh International to Chicago Midway is R 2,676. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
1 hour and 28 minutes is the average flight time from Pittsburgh International to Chicago Midway.
Southwest Airlines flies direct from Pittsburgh International to Chicago Midway.
As of March 2026, there are 22 flights per week flying from Pittsburgh International to Chicago Midway.
The cheapest month to fly from Pittsburgh International to Chicago Midway is usually May.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Pittsburgh International Airport to Chicago Midway Airport on Tuesday, 19 May 2026.
Yes – the average flight time is 1 hour and 28 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Delta and Southwest Airlines offer the cheapest flight tickets to Chicago Midway.

Flying from Pittsburgh International Airport (PIT) to Chicago Midway International Airport (MDW): what you need to know

  • Around 1 hour 25 minutes is how long you can expect to be travelling on a direct flight from Pittsburgh International Airport to Chicago Midway International Airport.

  • The timezone in Chicago is UTC-5, which is one hour behind Pittsburgh.

  • Flights from PIT to MDW start at 06:00 — the earliest with Southwest Airlines. The last service of the day is at 21:25 with Southwest Airlines. In total, there are 17 weekly Pittsburgh International Airport to Chicago Midway International Airport flights.

  • Your PIT to MDW flight won't wait if you're running late, so don't forget to check in on time. Arrive up to one hour in advance for domestic flights and two hours ahead when you're flying internationally.

  • Travelling during a peak time such as July? School holidays and other popular periods can mean longer queues and delays at check-in and security. Be extra cautious and arrive up to four hours before an international flight and two hours before a domestic departure.

  • Jetting into Chicago (and then exploring more of United States!) is a breeze with Southwest Airlines. This popular carrier has direct flights from Pittsburgh International Airport to Chicago Midway International Airport.

  • The majority of travellers choose to travel with Southwest Airlines on this route.

  • The most punctual carrier that operates PIT to MDW flights is Southwest Airlines. Its services arrive as planned 75.74% of the time.

  • If you want to break up your flight, simply deselect 'Direct flights only' when searching for your ticket from Pittsburgh International Airport to Chicago Midway International Airport. These are the most popular stopovers between PIT and MDW:

    • Detroit Metropolitan Wayne County Airport

    • Raleigh-Durham International Airport

    • Baltimore/Wash International Thurgood Marshall Airport

How to find the cheapest flights from Pittsburgh International Airport (PIT) to Chicago Midway International Airport (MDW)

  • R 1,170 is currently the best price for a one-way Pittsburgh International Airport to Chicago Midway International Airport flight. Return flights start from R 2,676. These fares may change depending on availability.

  • To get cheap tickets from PIT to MDW, book your trip seven months ahead of your departure date.

  • Schedule your trip for June. That's the cheapest month for flights from Pittsburgh International Airport to Chicago Midway International Airport. If you're flexible on when you fly, use the 'Whole month' tool to see the cheapest airfare across each month.

  • Picking up cheap flights from PIT to MDW couldn't be easier with Price Alerts. All you need to do is set up one of these automatic alerts and we'll get in touch when a new deal comes up.

  • Lock in the perfect flight for you by using the filters. To see the 'Cheapest,' 'Best' or 'Fastest' flights from Pittsburgh International Airport to Chicago Midway International Airport, use the 'Sort by' function. You can also filter results by departure and arrival times, airline, and journey duration.

Handy information about Pittsburgh International Airport (PIT)

  • PIT is located at 1000 Airport Boulevard.

  • Of all flights leaving Pittsburgh International Airport, 76.88% arrive as scheduled at their destination.

  • Pittsburgh International Airport is around 27 kilometres from central Pittsburgh. If you're ride-sharing, catching a cab or driving from the centre, it'll take 25 minutes or so to arrive, depending on the traffic.

  • Get your break off to a relaxed start by staying near PIT. Whether you're taking an early flight from Pittsburgh International Airport to Chicago Midway International Airport or just don't want to be rushed, these stays are perfect:

Arriving at Chicago Midway International Airport (MDW)

  • The last thing you need is a lengthy trip to your hotel if you're landing late on a Pittsburgh International Airport to Chicago Midway International Airport flight. Reserve one of these accommodation options near MDW instead:

  • Begin your adventure by picking up a Chicago Midway International Airport rental car. Grab your wheels from Dollar, Hertz or Budget and explore beyond Chicago's main sights.

  • Lock in the lowest price by reserving your vehicle from Chicago Midway International Airport about four weeks in advance of your trip.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • The address for MDW is 5700 South Cicero.

  • Chicago Midway International Airport is approximately 19 kilometres from central Chicago. Driving there takes about 20 minutes.

  • Travelling to the centre on public transport takes roughly 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

  • The quietest month for a flight from Pittsburgh International Airport to Chicago Midway International Airport is May, while July is the busiest. Pick the ideal time to visit Chicago based on whether you prefer a more relaxed vibe or a faster pace.

  • The warmest month in Chicago is July, with the temperature ranging between 15ºC (59ºF) and 29ºC (84ºF). Book your flights from Pittsburgh International Airport to Chicago Midway International Airport in this month if you enjoy this type of weather.

  • If you want to travel in cooler conditions, search for a cheap ticket from PIT to MDW in January. Temperatures average between -12ºC (10ºF) and 3ºC (37ºF) then.

Explore more of United States

  • Chicago has its own special appeal, but there are so many other corners of United States you'll want to see. About 451 kilometres south-east of Chicago, a trip to Columbus will keep your itinerary packed. Start with popular sights like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another must-experience destination in United States and is around 257 kilometres south-east of Chicago. No trip is complete without dropping by The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.