$39 Cheap flights from Pittsburgh Intl. to Midway Intl. (PIT to MDW)

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

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 $77 round trip and $39 one way. Prices and availability subject to change. Additional terms may apply.

Mon, Jul 7 - Thu, Jul 10
PIT
Pittsburgh
MDW
Chicago
$77 Roundtrip, found 11 hours ago
$77
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Mon, Jul 7 from Pittsburgh to Chicago, returning Thu, Jul 10, priced at $77 found 11 hours ago
Mon, Jul 7 - Thu, Jul 10
PIT
Pittsburgh
MDW
Chicago
$107 Roundtrip, found 11 hours ago
$107
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Mon, Jul 7 from Pittsburgh to Chicago, returning Thu, Jul 10, priced at $107 found 11 hours ago
Mon, Jul 7 - Thu, Jul 10
PIT
Pittsburgh
MDW
Chicago
$127 Roundtrip, found 11 hours ago
$127
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Mon, Jul 7 from Pittsburgh to Chicago, returning Thu, Jul 10, priced at $127 found 11 hours ago
Mon, Jul 7 - Thu, Jul 10
PIT
Pittsburgh
MDW
Chicago
$137 Roundtrip, found 11 hours ago
$137
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Mon, Jul 7 from Pittsburgh to Chicago, returning Thu, Jul 10, priced at $137 found 11 hours ago
Mon, Jul 7 - Thu, Jul 10
PIT
Pittsburgh
MDW
Chicago
$142 Roundtrip, found 11 hours ago
$142
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Mon, Jul 7 from Pittsburgh to Chicago, returning Thu, Jul 10, priced at $142 found 11 hours ago
Mon, Jul 7 - Thu, Jul 10
PIT
Pittsburgh
MDW
Chicago
$152 Roundtrip, found 11 hours ago
$152
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Mon, Jul 7 from Pittsburgh to Chicago, returning Thu, Jul 10, priced at $152 found 11 hours ago
Fri, May 30 - Mon, Jun 2
PIT
Pittsburgh
MDW
Chicago
$164 Roundtrip, found 6 days ago
$164
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, May 30 from Pittsburgh to Chicago, returning Mon, Jun 2, priced at $164 found 6 days ago
Mon, Jul 7 - Thu, Jul 10
PIT
Pittsburgh
MDW
Chicago
$171 Roundtrip, found 11 hours ago
$171
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Mon, Jul 7 from Pittsburgh to Chicago, returning Thu, Jul 10, priced at $171 found 11 hours ago
Fri, May 30 - Mon, Jun 2
PIT
Pittsburgh
MDW
Chicago
$173 Roundtrip, found 6 days ago
$173
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, May 30 from Pittsburgh to Chicago, returning Mon, Jun 2, priced at $173 found 6 days ago
Wed, Jul 2 - Wed, Jul 2
PIT
Pittsburgh
MDW
Chicago
$177 Roundtrip, found 18 hours ago
$177
Roundtrip
found 18 hours ago
Select Delta flight, departing Wed, Jul 2 from Pittsburgh to Chicago, returning Wed, Jul 2, priced at $177 found 18 hours ago

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham South Holland

Super 8 by Wyndham South Holland

2 out of 5
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Chicago (ORD)
Country Inn & Suites by Radisson, Schaumburg, IL

Country Inn & Suites by Radisson, Schaumburg, IL

3 out of 5
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Chicago (ORD)
Stone Creek Inn

Stone Creek Inn

2.5 out of 5
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Chicago (ORD)
Holiday Inn Express & Suites Prospect Heights by IHG

Holiday Inn Express & Suites Prospect Heights by IHG

3 out of 5
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Chicago (ORD)
HYATT house Chicago/Naperville/Warrenville

HYATT house Chicago/Naperville/Warrenville

3 out of 5
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Chicago (ORD)
Don't see what you're looking for?
See all available trips from Pittsburgh Intl. to Midway Intl.
View all trips

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
0 hours 30 mins
Earliest Departure Time
6:20AM CDT
Latest Departure Time
7:30PM CDT
Lowest Flight Price
$77

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 $77 and $177. 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 $39. 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 0 hour(s) 30 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, July 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. 

*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.