$46 Cheap Flights from Pittsburgh (PIT) to Chicago (MDW)

View $46 flight on Mon, Nov 24, 2025Opens in a new window

Popular airlines from Pittsburgh Intl. Airport (PIT) to Chicago Midway Airport (MDW)

Cheap Flights from Pittsburgh to Chicago (PIT-MDW)

Prices were available within the past 7 days and start at $46 for one-way flights and $91 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Thu, Dec 25 - Thu, Jan 1
PIT
Pittsburgh
MDW
Chicago
$91 Roundtrip, found 5 hours ago
$91
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Thu, Dec 25 from Pittsburgh to Chicago, returning Thu, Jan 1, priced at $91 found 5 hours ago
Southwest Airlines
Sat, Jan 17 - Sun, Jan 18
PIT
Pittsburgh
MDW
Chicago
$101 Roundtrip, found 15 hours ago
$101
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Sat, Jan 17 from Pittsburgh to Chicago, returning Sun, Jan 18, priced at $101 found 15 hours ago
Southwest Airlines
Sat, Jan 17 - Sun, Jan 18
PIT
Pittsburgh
MDW
Chicago
$111 Roundtrip, found 15 hours ago
$111
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Sat, Jan 17 from Pittsburgh to Chicago, returning Sun, Jan 18, priced at $111 found 15 hours ago
Delta
Thu, Dec 25 - Thu, Jan 1
PIT
Pittsburgh
MDW
Chicago
$124 Roundtrip, found 5 hours ago
$124
Roundtrip
found 5 hours ago
Select Delta flight, departing Thu, Dec 25 from Pittsburgh to Chicago, returning Thu, Jan 1, priced at $124 found 5 hours ago
Southwest Airlines
Fri, Oct 31 - Sun, Nov 2
PIT
Pittsburgh
MDW
Chicago
$135 Roundtrip, found 11 hours ago
$135
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Fri, Oct 31 from Pittsburgh to Chicago, returning Sun, Nov 2, priced at $135 found 11 hours ago
Southwest Airlines
Fri, Oct 31 - Sun, Nov 2
PIT
Pittsburgh
MDW
Chicago
$145 Roundtrip, found 11 hours ago
$145
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Fri, Oct 31 from Pittsburgh to Chicago, returning Sun, Nov 2, priced at $145 found 11 hours ago
Southwest Airlines
Tue, Dec 16 - Wed, Dec 17
PIT
Pittsburgh
MDW
Chicago
$148 Roundtrip, found 4 days ago
$148
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Dec 16 from Pittsburgh to Chicago, returning Wed, Dec 17, priced at $148 found 4 days ago
Southwest Airlines
Thu, Dec 25 - Thu, Jan 1
PIT
Pittsburgh
MDW
Chicago
$151 Roundtrip, found 5 hours ago
$151
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Thu, Dec 25 from Pittsburgh to Chicago, returning Thu, Jan 1, priced at $151 found 5 hours ago
Delta
Thu, Dec 25 - Thu, Jan 1
PIT
Pittsburgh
MDW
Chicago
$154 Roundtrip, found 5 hours ago
$154
Roundtrip
found 5 hours ago
Select Delta flight, departing Thu, Dec 25 from Pittsburgh to Chicago, returning Thu, Jan 1, priced at $154 found 5 hours ago
Frontier Airlines
Fri, Oct 24 - Fri, Oct 31
PIT
Pittsburgh
MDW
Chicago
$154 Roundtrip, found 1 day ago
$154
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Oct 24 from Pittsburgh to Chicago, returning Fri, Oct 31, priced at $154 found 1 day ago

Find the cheapest month to fly from Pittsburgh (PIT) to Chicago (MDW)

September is typically the cheapest month to fly

From $76 - $421 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $117
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $117

Frequently asked questions

How much does a flight from Pittsburgh Intl. Airport (PIT) to Midway Intl. Airport (MDW) cost?
Secure a cheap one-way flight from $46 or cheap return flight from $91 from Pittsburgh Intl. Airport (PIT) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Pittsburgh Intl. Airport (PIT) to Midway Intl. Airport (MDW)?
The cheapest month to fly from PIT to MDW is December, when demand is low. Off-peak months are generally when airlines offer better prices between these airports.
Which airlines fly direct from Pittsburgh Intl. Airport (PIT) to Midway Intl. Airport (MDW)?
Fly directly from Pittsburgh Intl. Airport (PIT) to Midway Intl. Airport (MDW) on a Southwest Airlines flight.
What is the cheapest airline that flies from Pittsburgh Intl. Airport (PIT) to Midway Intl. Airport (MDW)?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from PIT to MDW. Then, sort your results by "Price (lowest to highest)" to score a good deal.
How many flights per day from Pittsburgh Intl. Airport (PIT) to Midway Intl. Airport (MDW)?
With, on average, 2 nonstop flights that operate from Pittsburgh Intl. Airport (PIT) to Midway Intl. Airport (MDW) daily, you'll be jetting off in no time.
What are the most popular departure times for flights from Pittsburgh Intl. Airport (PIT) to Midway Intl. Airport (MDW)?
Flights between PIT and MDW are their busiest at 7 PM. If you want a less crowded experience and possibly cheaper prices, choose a time outside the usual busy windows.
What day of the week has the most flights from PIT to MDW?
If you depart on a Wednesday, you'll get the widest range of choices for flights from Pittsburgh Intl. Airport (PIT) to Midway Intl. Airport (MDW).
What is the earliest flight from Pittsburgh Intl. Airport (PIT) to Midway Intl. Airport (MDW)?
Pittsburgh Intl. Airport (PIT)'s earliest flight to Midway Intl. Airport (MDW) takes off at approximately 7:05AM UTC-5. With a total journey time of 1h 35m, you'll arrive at around 7:40AM UTC-6.
How long does it take to fly from Pittsburgh Intl. Airport (PIT) to Midway Intl. Airport (MDW)?
Flights from PIT to MDW have an average travel time of 1 hour and 31 minutes. The distance between the two is 400 mi.
What airline has the least delays from PIT to MDW?
Consider traveling with Southwest Airlines if you'd like to go straight from Pittsburgh Intl. Airport (PIT) to Midway Intl. Airport (MDW) without any holdups. This airline has the best track record for punctuality, with an on-time performance of 90%. Want to get notified of any changes? You can check your flight status using the Expedia App.
What is the best time to fly from Pittsburgh Intl. Airport (PIT) to Midway Intl. Airport (MDW)?
Opt for a flight from Pittsburgh Intl. Airport (PIT) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the likelihood of delays. Departures after this hour are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Pittsburgh Intl. Airport (PIT)?
Take a direct flight from Pittsburgh Intl. Airport (PIT) to Chicago and touch down at O'Hare Intl. Airport (ORD). Another arrival point to this destination is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Pittsburgh Intl. Airport (PIT) to Midway Intl. Airport (MDW) last-minute?
Waiting until just before your departure to book your flight from PIT to MDW often results in higher prices. While you may come across some last-minute offers, they're not always guaranteed. Be flexible with your travel plans for the best chance of scoring a bargain.
Is it cheaper to book a PIT to MDW flight and hotel package?
You'll typically save money by securing a PIT to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one place. After selecting your preferred accommodations and flights, consider adding extras like car rentals, activities and tours.
Can I cancel or change the date of my flight from Pittsburgh Intl. Airport (PIT) to Midway Intl. Airport (MDW)?
Typically, it's possible to cancel or reschedule your PIT to MDW flight. However, for bookings made more than 24 hours ago, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find further details on our Customer Service portal.

Travel information

Origin airport
Pittsburgh Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$91
Distance
399 mi
Average flight time
1 hour 7 mins

Book with confidence

Pittsburgh to Chicago Flights

The cheapest times to fly from Pittsburgh to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Pittsburgh to Chicago are during the month of December. You can find some of the cheapest flights from Pittsburgh to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Pittsburgh to Chicago

Sunday is one of the best days to book for cheap flights from Pittsburgh to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Pittsburgh to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Pittsburgh to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $46 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Pittsburgh to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Pittsburgh to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Pittsburgh to Chicago Flights

Explore a world of travel with Expedia

*Available to One Key members.