$72 Cheap flights from Pittsburgh Intl. to Midway Intl. (PIT to MDW)

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Find The Best Dates To Fly from Pittsburgh Intl. to Midway Intl.

Compare Flight Prices from Pittsburgh to Chicago

Affordable Airfare Tickets from PIT to MDW Airport

The cheapest flights to Midway Intl. found within the past 7 days were $139 round trip and $72 one way. Prices and availability subject to change. Additional terms may apply.

Sat, Sep 5 - Sun, Sep 6
PIT
Pittsburgh
MDW
Chicago
$139 Roundtrip, found 1 day ago
$139
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Pittsburgh to Chicago, returning Sun, Sep 6, priced at $139 found 1 day ago
Sat, Sep 5 - Sun, Sep 6
PIT
Pittsburgh
MDW
Chicago
$149 Roundtrip, found 1 day ago
$149
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Pittsburgh to Chicago, returning Sun, Sep 6, priced at $149 found 1 day ago
Sun, Sep 6 - Fri, Sep 11
PIT
Pittsburgh
MDW
Chicago
$155 Roundtrip, found 2 days ago
$155
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sun, Sep 6 from Pittsburgh to Chicago, returning Fri, Sep 11, priced at $155 found 2 days ago
Sun, Sep 6 - Fri, Sep 11
PIT
Pittsburgh
MDW
Chicago
$159 Roundtrip, found 2 days ago
$159
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Sep 6 from Pittsburgh to Chicago, returning Fri, Sep 11, priced at $159 found 2 days ago
Sat, Sep 5 - Thu, Sep 10
PIT
Pittsburgh
MDW
Chicago
$167 Roundtrip, found 2 days ago
$167
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Pittsburgh to Chicago, returning Thu, Sep 10, priced at $167 found 2 days ago
Fri, Sep 11 - Sat, Sep 12
PIT
Pittsburgh
MDW
Chicago
$174 Roundtrip, found 2 days ago
$174
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Sep 11 from Pittsburgh to Chicago, returning Sat, Sep 12, priced at $174 found 2 days ago
Sat, Sep 5 - Thu, Sep 10
PIT
Pittsburgh
MDW
Chicago
$177 Roundtrip, found 2 days ago
$177
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Pittsburgh to Chicago, returning Thu, Sep 10, priced at $177 found 2 days ago
Sat, Sep 5 - Thu, Sep 10
PIT
Pittsburgh
MDW
Chicago
$182 Roundtrip, found 2 days ago
$182
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Pittsburgh to Chicago, returning Thu, Sep 10, priced at $182 found 2 days ago
Fri, Sep 11 - Sat, Sep 12
PIT
Pittsburgh
MDW
Chicago
$184 Roundtrip, found 2 days ago
$184
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Sep 11 from Pittsburgh to Chicago, returning Sat, Sep 12, priced at $184 found 2 days ago
Sun, Sep 6 - Fri, Sep 11
PIT
Pittsburgh
MDW
Chicago
$185 Roundtrip, found 2 days ago
$185
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Sep 6 from Pittsburgh to Chicago, returning Fri, Sep 11, priced at $185 found 2 days ago

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $988, price is now $678 per person
$678
per person
Sep 19 - Sep 22
found 22 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,157, price is now $792 per person
$792
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,182, price is now $810 per person
$810
per person
Sep 19 - Sep 22
found 21 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,031, price is now $711 per person
$711
per person
Sep 9 - Sep 12
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $1,235, price is now $858 per person
$858
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Chicago (ORD)
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Frequently asked questions

Can I catch a flight from Pittsburgh Airport to MDW right now?
It's always wise to find out about any travel advice reports and quarantine requirements in place in your destination city. Ensure you go to the Covid-19 Travel Advisor for up-to-date information on booking a flight to Chicago Airport.
Are there direct flights from PIT to Chicago Airport?
If you just want to get going on your adventures in Chicago, look into Southwest Airlines. They advertise nonstop services from Pittsburgh Intl. Airport (PIT) to Chicago Airport.
If I am not able to travel due to COVID-19, can I change my booking to a later date?
For more info about changing your flight to Chicago Airport, please visit our Customer Service Portal.
How long is the flight from Pittsburgh Intl. Airport (PIT) to Midway Intl. Airport (MDW)?
Flying from Pittsburgh Intl. Airport (PIT) to Midway Airport is easy as the flight normally takes 1 hour and 29 minutes. With such a short flight time, there's a good chance you'll exit the plane feeling as fresh as when you got on.
What is the flight distance from Pittsburgh Intl. Airport (PIT) to Chicago Airport?
From PIT, you'll travel 400 mi before landing at Chicago Airport. That should give you enough time to read a few chapters of your book or maybe even manage a nap.
What airlines fly from Pittsburgh Intl. Airport (PIT) to Chicago Airport?
Looking to fly nonstop from Pittsburgh to Chicago? No sweat. Southwest Airlines offers 104 flights each month and is a popular choice with many worldly wanderers.
What airlines have practices regarding COVID-19 in place and use social distancing?
From the moment you enter the departure terminal to when you leave the arrivals terminal, if you're flying with Southwest Airlines, Delta or Volaris you can be sure that COVID-19 measures and social distancing rules have been adhered to. Many airlines have introduced capped capacity flights and keeping the middle seat empty.
What is the best day to buy a plane ticket?
This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that is when prices are generally at their highest.
What are the cheapest days to fly?
Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2021, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.
How far in advance can you book a flight?
Trying to figure out how early you should book your flight? It's possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Flight information from Pittsburgh to Chicago

 

Traveling From
Pittsburgh Intl.
Traveling To
Midway Intl.
Shortest Flight Time
 hours mins
Earliest Departure Time
Latest Departure Time
Lowest Flight Price
$139

Route Info

Flight path for flights from Pittsburgh International Airport to Chicago Midway International Airport.


Origin:
PIT - Pittsburgh International Airport
Destination:
MDW - Chicago Midway International Airport
Distance:
403.00 miles


Discover our best flights from Pittsburgh PIT to Chicago MDW. 

With 20 airlines to choose from on Travelocity, you can easily find the best option for you. Use our filters to sort by price, compare airlines, and find the most convenient flight times. 

 

Find our best return flights from Pittsburgh PIT to Chicago MDW at the right price  

Airfares to Chicago MDW from Pittsburgh PIT currently cost between $139 and $185. It’s usually cheaper to book a round trip than two separate one-way flights. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way flights from Pittsburgh PIT to Chicago MDW 

If you want to be flexible about when you return, or keep your travel options open ended, a one-way flight could be just the ticket! You’ll find one-way airfares from Pittsburgh PIT to Chicago MDW on Travelocity starting at $72. Prices and availability subject to change. Additional terms may apply. 

 

Get to Chicago MDW from Pittsburgh PIT quicker with direct flights. 

Get to Chicago faster, without the hassle of changing planes and moving baggage, by booking a direct flight. Expect your direct flight to MDW from PIT to take around hour(s) min(s).  

 

Find our cheapest airfares for flights from Pittsburgh PIT to Chicago MDW

Find cheap flight deals by using our search filters to sort results starting with the lowest price airfares to MDW from PIT. Our Price Match Promise means if you find a lower rate on Travelocity.com or on another US-based website within 24 hours of booking, we’ll credit or refund the difference.  

 

Get our best airfare deals for your flight from Pittsburgh PIT to Chicago MDW today 

If you’re flexible about when you travel, September is usually the cheapest month to fly from Pittsburgh PIT to Chicago MDW. If you need to be more specific, search by date and arrival and departure times.Then, compare prices across different airlines, and sort results by lowest price first. 

 

Book flexible airline tickets for flights to Chicago MDW from Pittsburgh PIT 

Some airlines let you change your travel dates without charging a fee. Use our ‘no change fee’ filter to see which flights to MDW from PIT have this option.  

 

Travel with confidence when you book flights to Chicago MDW from Pittsburgh PIT with Travelocity 

We’ve secured fantastic deals with all the main airline carriers and it’s easy to compare, choose, and book with Travelocity. With 24/7 customer service and our free 'App', we’ll always keep you moving. 

Explore More Ways to Travel with Travelocity

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.