Cheap Flight Tickets from Pittsburgh (PIT) to Chicago (MDW), Starting at $320

Good to Know: Cheapest and Fastest PIT - MDW Flights

Useful information for finding best airline tickets from Pittsburgh International to Chicago Midway International on your next trip.

Cheapest Round Trip Flight

$364

WN Southwest Airlines • 1 stop • 17h 15m

Jul 30 – Aug 02

The cheapest round trip flight from Pittsburgh to Chicago (PIT-MDW-PIT) is currently $364

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Cheapest Direct Flight

$320

WN Southwest Airlines • nonstop • 2h 10m

Jul 29

The cheapest nonstop flight from Pittsburgh to Chicago (PIT-MDW) is currently $320

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Fastest Flight

2h 5m

The fastest nonstop flight from Pittsburgh to Chicago (PIT-MDW) takes 2h 5m

Top Airlines Flying from Pittsburgh to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

Latest Flight Deals from Pittsburgh (PIT) to Chicago (MDW)

Compare and book low fare round-trip air tickets from Pittsburgh to Chicago. Ideal for travelers with confirmed return itineraries.

Jul 30 - Aug 02, Economy
WN
Pittsburgh → Chicago
17h 15m
10:30 AM - 8:05 PM • 1 stop
WN
Pittsburgh → Chicago
2h 5m
7:40 AM - 10:05 AM • nonstop
$364
Southwest Airlines
Jul 30 - Aug 02, Economy
WN
Pittsburgh → Chicago
5h 55m
9:15 PM - 12:10 AM • 1 stop
WN
Pittsburgh → Chicago
2h 5m
7:40 AM - 10:05 AM • nonstop
$364
Southwest Airlines
Jul 30 - Aug 02, Economy
WN
Pittsburgh → Chicago
12h 20m
10:30 AM - 5:10 PM • 1 stop
WN
Pittsburgh → Chicago
2h 5m
7:40 AM - 10:05 AM • nonstop
$364
Southwest Airlines
Jul 30 - Aug 02, Economy
WN
Pittsburgh → Chicago
13h 30m
4:35 PM - 11:45 PM • 1 stop
WN
Pittsburgh → Chicago
2h 5m
7:40 AM - 10:05 AM • nonstop
$364
Southwest Airlines
Jul 30 - Aug 02, Economy
WN
Pittsburgh → Chicago
9h 10m
5:45 AM - 10:35 AM • 1 stop
WN
Pittsburgh → Chicago
2h 5m
7:40 AM - 10:05 AM • nonstop
$364
Southwest Airlines
Jul 30 - Aug 02, Economy
WN
Pittsburgh → Chicago
17h 25m
8:00 AM - 5:45 PM • 2 stops
WN
Pittsburgh → Chicago
2h 5m
7:40 AM - 10:05 AM • nonstop
$369
Southwest Airlines

Fly from Pittsburgh to Chicago with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Pittsburgh to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Pittsburgh to Chicago Flights

What are the airports in Pittsburgh?
PIT
What’s the most popular airline flying from PIT to MDW?
The most popular airline flying from Pittsburgh to Chicago are
Can I fly from PIT to MDW non-stop?
Yes, you can fly PIT to MDW non-stop on
Which airlines fly nonstop between Pittsburgh and Chicago?
The non-stop flights between Pittsburgh and Chicago are .
What’s the earliest departure time from PIT to MDW Airport?
The earliest flight leaves PIT at 5:45 am and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my Pittsburgh to Chicago flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from PIT to MDW?
Read the fare rules of the Pittsburgh to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Pittsburgh and Chicago?
operate flights between Pittsburgh and Chicago
How long does a flight from Pittsburgh to Chicago take?
It takes approximately 1 hour to fly non-stop from PIT to MDW, which is 402.18 miles by air.
Which airlines provide the cheapest flights from Pittsburgh (PIT) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from PIT were found on WN : USD 364
Do I need a passport to fly between PIT and MDW?
No
What’s the latest departure time from PIT to MDW ?
The last flight leaves PIT at 9:15 pm

Pittsburgh (PIT) to Chicago (MDW): Airport Information

Origin Airport Pittsburgh International , Pittsburgh, US
Destination Airport Chicago Midway International , Chicago, US
Distance 402 miles

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