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

View $46 flight on Tue, Aug 26, 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
Wed, Aug 27 - Sat, Aug 30
PIT
Pittsburgh
MDW
Chicago
$91 Roundtrip, found 2 hours ago
$91
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Wed, Aug 27 from Pittsburgh to Chicago, returning Sat, Aug 30, priced at $91 found 2 hours ago
Southwest Airlines
Thu, Sep 4 - Sat, Sep 6
PIT
Pittsburgh
MDW
Chicago
$94 Roundtrip, found 5 days ago
$94
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Sep 4 from Pittsburgh to Chicago, returning Sat, Sep 6, priced at $94 found 5 days ago
Southwest Airlines
Thu, Sep 18 - Mon, Sep 22
PIT
Pittsburgh
MDW
Chicago
$97 Roundtrip, found 3 hours ago
$97
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Thu, Sep 18 from Pittsburgh to Chicago, returning Mon, Sep 22, priced at $97 found 3 hours ago
Southwest Airlines
Wed, Aug 27 - Sat, Aug 30
PIT
Pittsburgh
MDW
Chicago
$101 Roundtrip, found 2 hours ago
$101
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Wed, Aug 27 from Pittsburgh to Chicago, returning Sat, Aug 30, priced at $101 found 2 hours ago
Southwest Airlines
Sat, Aug 30 - Mon, Sep 1
PIT
Pittsburgh
MDW
Chicago
$104 Roundtrip, found 1 hour ago
$104
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Sat, Aug 30 from Pittsburgh to Chicago, returning Mon, Sep 1, priced at $104 found 1 hour ago
Southwest Airlines
Wed, Oct 1 - Wed, Oct 29
PIT
Pittsburgh
MDW
Chicago
$106 Roundtrip, found 6 hours ago
$106
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Wed, Oct 1 from Pittsburgh to Chicago, returning Wed, Oct 29, priced at $106 found 6 hours ago
Southwest Airlines
Thu, Sep 18 - Mon, Sep 22
PIT
Pittsburgh
MDW
Chicago
$107 Roundtrip, found 3 hours ago
$107
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Thu, Sep 18 from Pittsburgh to Chicago, returning Mon, Sep 22, priced at $107 found 3 hours ago
Southwest Airlines
Sat, Nov 1 - Mon, Nov 3
PIT
Pittsburgh
MDW
Chicago
$109 Roundtrip, found 2 hours ago
$109
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Sat, Nov 1 from Pittsburgh to Chicago, returning Mon, Nov 3, priced at $109 found 2 hours ago
Delta
Tue, Aug 19 - Sat, Aug 23
PIT
Pittsburgh
MDW
Chicago
$134 Roundtrip, found 5 hours ago
$134
Roundtrip
found 5 hours ago
Select Delta flight, departing Tue, Aug 19 from Pittsburgh to Chicago, returning Sat, Aug 23, priced at $134 found 5 hours ago
Frontier Airlines
Fri, Aug 15 - Sat, Aug 16
PIT
Pittsburgh
MDW
Chicago
$248 Roundtrip, found 2 days ago
$248
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Aug 15 from Pittsburgh to Chicago, returning Sat, Aug 16, priced at $248 found 2 days 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

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. Average driving time to city center is 23 minutes. Flights from $258
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $258
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

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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