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

View $46 flight on Tue, Aug 5, 2025Opens in a new window

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

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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
Tue, Aug 19 - Sat, Aug 23
PIT
Pittsburgh
MDW
Chicago
$91 Roundtrip, found 1 hour ago
$91
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Tue, Aug 19 from Pittsburgh to Chicago, returning Sat, Aug 23, priced at $91 found 1 hour ago
Southwest Airlines
Thu, Sep 4 - Sat, Sep 6
PIT
Pittsburgh
MDW
Chicago
$94 Roundtrip, found 4 days ago
$94
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Thu, Sep 4 from Pittsburgh to Chicago, returning Sat, Sep 6, priced at $94 found 4 days ago
Southwest Airlines
Thu, Aug 28 - Mon, Sep 1
PIT
Pittsburgh
MDW
Chicago
$97 Roundtrip, found 1 hour ago
$97
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Thu, Aug 28 from Pittsburgh to Chicago, returning Mon, Sep 1, priced at $97 found 1 hour ago
Southwest Airlines
Tue, Aug 19 - Sat, Aug 23
PIT
Pittsburgh
MDW
Chicago
$101 Roundtrip, found 1 hour ago
$101
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Tue, Aug 19 from Pittsburgh to Chicago, returning Sat, Aug 23, priced at $101 found 1 hour ago
Southwest Airlines
Thu, Aug 28 - Sat, Aug 30
PIT
Pittsburgh
MDW
Chicago
$104 Roundtrip, found 1 hour ago
$104
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Thu, Aug 28 from Pittsburgh to Chicago, returning Sat, Aug 30, priced at $104 found 1 hour ago
Southwest Airlines
Sat, Sep 13 - Tue, Sep 16
PIT
Pittsburgh
MDW
Chicago
$106 Roundtrip, found 5 hours ago
$106
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sat, Sep 13 from Pittsburgh to Chicago, returning Tue, Sep 16, priced at $106 found 5 hours ago
Southwest Airlines
Thu, Aug 28 - Mon, Sep 1
PIT
Pittsburgh
MDW
Chicago
$107 Roundtrip, found 1 hour ago
$107
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Thu, Aug 28 from Pittsburgh to Chicago, returning Mon, Sep 1, priced at $107 found 1 hour ago
Southwest Airlines
Sat, Sep 20 - Mon, Sep 22
PIT
Pittsburgh
MDW
Chicago
$109 Roundtrip, found 3 hours ago
$109
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Sat, Sep 20 from Pittsburgh to Chicago, returning Mon, Sep 22, priced at $109 found 3 hours ago
Delta
Tue, Aug 19 - Sat, Aug 23
PIT
Pittsburgh
MDW
Chicago
$134 Roundtrip, found 1 hour ago
$134
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Aug 19 from Pittsburgh to Chicago, returning Sat, Aug 23, priced at $134 found 1 hour ago
Frontier Airlines
Fri, Aug 15 - Sat, Aug 16
PIT
Pittsburgh
MDW
Chicago
$248 Roundtrip, found 1 day ago
$248
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Aug 15 from Pittsburgh to Chicago, returning Sat, Aug 16, priced at $248 found 1 day ago

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

August is typically the cheapest month to fly

From $81 - $359 per traveler.

Graph displaying average flight prices per month

0
Flights from Pittsburgh (PIT) to Chicago (MDW)
Origin airport
Pittsburgh Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$91
Distance
399 mi

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 August. 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.

 

Frequently asked questions

How much does a flight from Pittsburgh Intl. Airport (PIT) to Midway Intl. Airport (MDW) cost?
Cheap round-trip fares from Pittsburgh Intl. Airport (PIT) to Midway Intl. Airport (MDW) start at $61. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines flight leaving PIT on August 6 2025 and touching down at MDW. The price was last updated on July 12 2025 and has not changed since.
What is the cheapest month to fly from PIT to MDW?
The cheapest flights from PIT to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 PIT to MDW?
At the moment, the cheapest airline offering one-way flights from PIT to MDW is Southwest Airlines. You can jet off on this route from $31. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from PIT on October 7 2025. Prices were last updated on July 12 2025 and have not changed since.
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.

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