$55 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.

Amazing PIT to MDW Flight Deals

The cheapest flights to Midway Intl. found within the past 7 days were $110 round trip and $55 one way. Prices and availability subject to change. Additional terms may apply.

Wed, Aug 14 - Tue, Aug 20
PIT
Pittsburgh
MDW
Chicago
$110 Roundtrip, found 2 hours ago
$110
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Aug 14 from Pittsburgh to Chicago, returning Tue, Aug 20, priced at $110 found 2 hours ago
Fri, Sep 6 - Sat, Sep 14
PIT
Pittsburgh
MDW
Chicago
$113 Roundtrip, found 1 day ago
$113
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Sep 6 from Pittsburgh to Chicago, returning Sat, Sep 14, priced at $113 found 1 day ago
Tue, Oct 1 - Wed, Oct 2
PIT
Pittsburgh
MDW
Chicago
$116 Roundtrip, found 21 hours ago
$116
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Tue, Oct 1 from Pittsburgh to Chicago, returning Wed, Oct 2, priced at $116 found 21 hours ago
Wed, Aug 14 - Tue, Aug 20
PIT
Pittsburgh
MDW
Chicago
$117 Roundtrip, found 2 days ago
$117
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Aug 14 from Pittsburgh to Chicago, returning Tue, Aug 20, priced at $117 found 2 days ago
Fri, Aug 16 - Tue, Aug 20
PIT
Pittsburgh
MDW
Chicago
$124 Roundtrip, found 2 days ago
$124
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Aug 16 from Pittsburgh to Chicago, returning Tue, Aug 20, priced at $124 found 2 days ago
Wed, Aug 14 - Wed, Aug 21
PIT
Pittsburgh
MDW
Chicago
$127 Roundtrip, found 3 days ago
$127
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Aug 14 from Pittsburgh to Chicago, returning Wed, Aug 21, priced at $127 found 3 days ago
Tue, Jun 18 - Wed, Jun 19
PIT
Pittsburgh
MDW
Chicago
$128 Roundtrip, found 4 days ago
$128
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Jun 18 from Pittsburgh to Chicago, returning Wed, Jun 19, priced at $128 found 4 days ago
Fri, Aug 16 - Sat, Aug 17
PIT
Pittsburgh
MDW
Chicago
$131 Roundtrip, found 2 days ago
$131
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Aug 16 from Pittsburgh to Chicago, returning Sat, Aug 17, priced at $131 found 2 days ago
Wed, Aug 14 - Sun, Aug 18
PIT
Pittsburgh
MDW
Chicago
$133 Roundtrip, found 2 hours ago
$133
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Aug 14 from Pittsburgh to Chicago, returning Sun, Aug 18, priced at $133 found 2 hours ago
Fri, Sep 20 - Sun, Sep 22
PIT
Pittsburgh
MDW
Chicago
$138 Roundtrip, found 21 hours ago
$138
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Fri, Sep 20 from Pittsburgh to Chicago, returning Sun, Sep 22, priced at $138 found 21 hours ago

Best Midway Intl. Flight and Hotel Packages

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
W Chicago - City Center

W Chicago - City Center

4 out of 5
Save 100% on your flight
per person
Jul 18 - Jul 22
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Chicago (ORD)
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Save 100% on your flight
per person
Jul 18 - Jul 22
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Chicago (ORD)
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Save 100% on your flight
per person
Jul 18 - Jul 22
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Chicago (ORD)
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
Save 100% on your flight
per person
Jul 18 - Jul 22
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
per person
Jul 18 - Jul 22
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.

 

Traveling From
Pittsburgh Intl.
Traveling To
Midway Intl.
Shortest Flight Time
0 hours 35 mins
Earliest Departure Time
6:45AM CDT
Latest Departure Time
8:15PM CDT
Lowest Flight Price
$110

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 $110 and $138. 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 $55. 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) 35 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, August 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.