MDW - PIT

$69 Find Cheap Flights from Chicago Midway Airport to Pittsburgh

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Pittsburgh departing on 4/29. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Pittsburgh

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Pittsburgh, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Pittsburgh, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$187
Southwest
Sat 4/4Wed 4/8
MDW - PIT • Non-stop
Cheapest non-stop
$187
Southwest
Mon 5/18Wed 5/20
MDW - PIT • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Midway's compact terminal eases navigation and access.
The 28X Airport Flyer bus is budget-friendly to downtown.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Southwest
Cheapest • from $187 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 1h 21m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Southwest
Most punctual • 86% on-time
Morning flights
Best time • Fewest delays
Insights
Insights
Insights
Insights
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Pittsburgh!
Flight Deals
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Flight Deals

Cheap Flights from Midway to Pittsburgh (MDW-PIT)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Pittsburgh that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Pittsburgh

Sat, Apr 4 - Wed, Apr 8
Southwest Logo
8:00 am - 10:25 am
MDW
-
PIT
1h 25mnonstop
Southwest Logo
6:55 pm - 10:15 pm
PIT
-
MDW
4h 20m
1 stop
$187Southwest
Thu, Apr 9 - Mon, Apr 13
Southwest Logo
2:10 pm - 11:10 pm
MDW
-
PIT
8h 00m
2 stops
Southwest Logo
1:35 pm - 2:05 pm
PIT
-
MDW
1h 30mnonstop
$192Southwest
Mon, Apr 13 - Thu, Apr 16
Delta Logo
6:38 pm - 10:56 pm
MDW
-
PIT
3h 18m
1 stop
Delta Logo
6:40 am - 8:47 am
PIT
-
MDW
3h 07m
1 stop
$197Delta
Sat, Apr 4 - Wed, Apr 8
Southwest Logo
8:00 am - 10:25 am
MDW
-
PIT
1h 25mnonstop
Southwest Logo
6:25 am - 3:45 pm
PIT
-
MDW
10h 20m
2 stops
$198Southwest
Thu, Apr 9 - Mon, Apr 13
Southwest Logo
2:10 pm - 11:10 pm
MDW
-
PIT
8h 00m
2 stops
Southwest Logo
8:10 pm - 11:30 pm
PIT
-
MDW
4h 20m
1 stop
$202Southwest
Wed, Apr 15 - Sat, Apr 18
Southwest Logo
12:45 pm - 10:10 pm
MDW
-
PIT
8h 25m
2 stops
Southwest Logo
6:00 am - 12:15 pm
PIT
-
MDW
7h 15m
2 stops
$207Southwest
Mon, Apr 20 - Wed, Apr 22
Southwest Logo
7:50 am - 12:55 pm
MDW
-
PIT
4h 05m
1 stop
Southwest Logo
6:25 am - 3:45 pm
PIT
-
MDW
10h 20m
2 stops
$208Southwest
Wed, Apr 8 - Tue, Apr 14
Delta Logo
6:07 pm - 12:17 am
MDW
-
PIT
5h 10m
1 stop
Delta Logo
6:00 am - 9:56 am
PIT
-
MDW
4h 56m
1 stop
$217Delta
Sat, Apr 11 - Sat, Apr 18
Southwest Logo
5:25 pm - 11:00 pm
MDW
-
PIT
4h 35m
1 stop
Southwest Logo
7:15 am - 2:40 pm
PIT
-
MDW
8h 25m
2 stops
$222Southwest
Mon, Apr 20 - Thu, Apr 23
Southwest Logo
5:50 pm - 11:10 pm
MDW
-
PIT
4h 20m
1 stop
Southwest Logo
8:00 pm - 8:30 pm
PIT
-
MDW
1h 30mnonstop
$227Southwest
Booking Insights

KAYAK's insights & trends for Midway to Pittsburgh flights

Get data-powered insights and trends into flights from Midway to Pittsburgh to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Pittsburgh?

The average price of all round-trip flights from Chicago Midway Airport to Pittsburgh clicked on KAYAK for each day over the last 12 months.

For Chicago Midway Airport to Pittsburgh, Thursday is the cheapest day to fly on average and Saturday is the most expensive. Flying from Pittsburgh back to Chicago Midway Airport, the best deals are generally found on Thursday, with Sunday being the most expensive.

Can I save money by flying with a layover from Chicago Midway Airport to Pittsburgh?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $334, prices are generally cheapest when you fly direct.

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Expert advice

Expert advice for your flight from Midway to Pittsburgh

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Matt Meltzer

Matt Meltzer

Expert on PIT

Matt Meltzer has been a travel writer for over a decade, covering U.S. domestic locations and hotels for Thrillist, Fifty Grande, Matador Network, Conde Nast Traveler, and other top publications. He's won multiple travel journalism awards from the Society of American Travel Writers and North American Travel Journalists Association, and currently resides in South Florida.

Read more

Good to know

Low seasonSeptember
Cheapest flight$69
Best time to beat the crowds with an average 65% drop in price.
Most popular time to fly with an average 65% increase in price.
Flight from Chicago Midway Airport to Pittsburgh

When to book flights from Midway to Pittsburgh

Are your dates flexible? Find out the best times to travel from Midway to Pittsburgh based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Pittsburgh flights

  • What is the cheapest flight from Chicago Midway Airport to Pittsburgh?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Pittsburgh was $69 for a one-way ticket and $187 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Pittsburgh?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Pittsburgh?

    American Airlines, and Delta offer inflight Wi-Fi service on the Chicago Midway Airport to Pittsburgh flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Pittsburgh?

    The Airbus A319 is the aircraft model that flies most regularly on the Chicago Midway Airport to Pittsburgh flight route.

  • On which days can I fly direct from Chicago Midway Airport to Pittsburgh?

    There are nonstop flights from Chicago Midway Airport to Pittsburgh on a daily basis.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Pittsburgh?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Pittsburgh.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Pittsburgh?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Pittsburgh from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Pittsburgh?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Pittsburgh with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and PIT can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Pittsburgh?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Pittsburgh from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Pittsburgh

  • Looking for a cheap flight? 25% of our users found flights on this route for $238 or less one-way and $324 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Pittsburgh?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to Pittsburgh.
Find which airlines fly direct from Chicago Midway Airport to Pittsburgh Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Pittsburgh

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Pittsburgh to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airline flying from Midway to Pittsburgh

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Pittsburgh. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Pittsburgh? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4318 reviews
8.6Crew
8.1Boarding
8.0Comfort
7.0Food
7.5Entertainment
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

Everything you need to know for your flight from Midway to Pittsburgh

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Pittsburgh (PIT)