PIT to MDW (Pittsburgh to Chicago) Flights

Last Minute Flights from PIT to MDW

Best airfare and ticket deals for PIT to MDW flights are based on recent deals found by Expedia.com customers within the past 7 days.

OriginDestinationTravel DatesFlights From*
PITChicagoApril 28 to May 11$218
*Prices include taxes and fees

Cheapest PIT to MDW Flights

Best airfare and ticket deals for PIT to MDW flights are based on recent deals found by Expedia.com customers within the past 7 days.

OriginDestinationTravel DatesFlights From*
PITChicagoApril 30 to May 4$106
PITChicagoMay 7 to May 22$107
PITChicagoMay 20 to May 22$108
PITChicagoMay 21 to May 28$136
*Prices include taxes and fees
PIT to MDW Flight Details
Origin airport
Pittsburgh Intl.
Origin airport IATA code
PIT
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Distance
399 mi

Frequently asked questions

Which airlines with flights from Pittsburgh, PA Airport (PIT-Pittsburgh Intl.) to Chicago, IL Airport (MDW-Midway Intl.) allow free cancellation due to COVID-19?
Once all available flights are displayed for your preferred travel dates, check the “No change fee” box underneath the “Flexible change policies” filter. You’ll see your choices from PIT to Chicago Airport. You’ll want to go over the policies regarding COVID-19 cancellations before reserving your seat.
What airlines fly direct from PIT to Chicago, IL Airport (MDW-Midway Intl.)?
Southwest Airlines (WN) does. Book a fare on one of the 104 monthly flights that depart from Pittsburgh, PA Airport (PIT-Pittsburgh Intl.) and jet straight to Chicago Airport. Skipping a pesky stopover is a top way to begin your vacation.
How many flights are there from PIT to MDW?
Approximately 3 each day. If you’re in a big rush to head to Chicago, see if you can find an incredible last-minute deal from Pittsburgh, PA Airport (PIT-Pittsburgh Intl.) to Chicago, IL Airport (MDW-Midway Intl.) and then lock it in quick!
How long does it take to fly from Pittsburgh, PA Airport (PIT-Pittsburgh Intl.) to Chicago, IL Airport (MDW-Midway Intl.)?
The flight length from Pittsburgh, PA Airport (PIT-Pittsburgh Intl.) to Chicago, IL Airport (MDW-Midway Intl.) is approximately 1 hour and 29 minutes. The in-flight entertainment system isn’t always available on short journeys, so bring a magazine to flick through or download some new tunes on your smartphone.
What is the flight distance from Pittsburgh, PA Airport (PIT-Pittsburgh Intl.) to Chicago, IL Airport (MDW-Midway Intl.)?
Pittsburgh, PA Airport (PIT-Pittsburgh Intl.) to Chicago, IL Airport (MDW-Midway Intl.) is a short-haul trip of 400 miles (640 km). You’ll hardly have time to get comfortable in your seat before your wheels touch down in Chicago.
How many morning flights are there from PIT to MDW?
Every week, 10 flights set off from PIT to MDW before noon. Southwest Airlines (WN) lists 10 morning flights per week, with the earliest setting off at 10:30AM.
How many afternoon flights are there from PIT to MDW?
Select one of the 14 weekly afternoon and evening flights from PIT to MDW and sneak in some more sleep. Popular carrier Southwest Airlines (WN) has 14 of these flights which jet out from 4:10PM.
What is the earliest departure time out of Pittsburgh to Chicago?
6:30AM is the first flight that leaves from PIT, arriving at MDW at 8:00AM. Save precious minutes in the morning by having your suitcase packed and ready to be thrown into your rideshare.
What is the latest departure time out of Pittsburgh to Chicago?
From PIT, the last flight sets out at 7:55PM and lands at 9:25PM at MDW. If you’re not a fan of early starts, this is the flight to book.
What is the average price from Pittsburgh to Chicago?
Flights from PIT to MDW are available for around $106. You’ll want to get a move on, because fabulous fares get scooped up in a hurry! This price was available on Flights.com within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Pittsburgh to Chicago Flights

Whether it’s for an obligation or the sake of your sanity, sometimes you need to get away. Maybe you need flights from Pittsburgh to Chicago to attend your cousin’s wedding, to pitch a business idea to your boss, or perhaps simply to treat yourself to a mini vacation. Regardless of the reasons behind packing your bags and needing to find the cheapest flights from PIT to MDW, we’ve got you covered here at Flights.com.

We present you with some of the hottest deals on airfare so stop that Google flights search. We want you to spend less on your flight from Pittsburgh to Chicago, so you can spend more during your getaway. With Flights.com, you’ll find it simple to land airline tickets with itineraries matching your travel schedule. What’s more, we provide you with all the information you need to confidently make reservations on your family, business, or personal trip.