MDW - PIT

$69 Find Cheap Flights from Chicago Midway Airport to Pittsburgh - Compare and Save

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 7/4. 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

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$191
Typical prices: $247-$167
Southwest
Thu 8/6Mon 8/10
MDW - PIT • 1 stop
Cheapest non-stop
$210
Southwest
Sat 9/5Mon 9/7
MDW - PIT • Non-stop
Top airlines
Cheapest • from $191 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 1h 25m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Most punctual • 86% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Pittsburgh!
Flight Deals
Booking Insights
Expert advice
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

Thu, Aug 6 - Mon, Aug 10
Southwest Logo
5:55 am - 12:35 pm
MDW
-
PIT
5h 40m
1 stop
Southwest Logo
7:30 pm - 7:50 pm
PIT
-
MDW
1h 20mnonstop
$191Southwest
Thu, Aug 6 - Mon, Aug 10
Southwest Logo
9:20 am - 5:40 pm
MDW
-
PIT
7h 20m
2 stops
Southwest Logo
7:30 pm - 7:50 pm
PIT
-
MDW
1h 20mnonstop
$196Southwest
Thu, Aug 6 - Mon, Aug 10
Delta Logo
9:24 am - 3:33 pm
MDW
-
PIT
5h 09m
1 stop
Delta Logo
4:55 pm - 10:36 pm
PIT
-
MDW
6h 41m
1 stop
$201Delta
Thu, Aug 6 - Mon, Aug 10
Southwest Logo
9:20 am - 5:40 pm
MDW
-
PIT
7h 20m
2 stops
Southwest Logo
7:00 am - 12:15 pm
PIT
-
MDW
6h 15m
1 stop
$206Southwest
Sat, Sep 5 - Mon, Sep 7
Southwest Logo
3:10 pm - 5:30 pm
MDW
-
PIT
1h 20mnonstop
Southwest Logo
8:40 am - 9:00 am
PIT
-
MDW
1h 20mnonstop
$210Southwest
Thu, Aug 6 - Mon, Aug 10
Southwest Logo
9:20 am - 5:40 pm
MDW
-
PIT
7h 20m
2 stops
Southwest Logo
6:10 am - 12:15 pm
PIT
-
MDW
7h 05m
2 stops
$211Southwest
Wed, Jul 1 - Wed, Jul 8
Southwest Logo
7:50 am - 10:20 am
MDW
-
PIT
1h 30mnonstop
Southwest Logo
7:30 pm - 8:00 pm
PIT
-
MDW
1h 30mnonstop
$217Southwest
Tue, Aug 18 - Wed, Aug 26
Southwest Logo
6:20 pm - 8:45 pm
MDW
-
PIT
1h 25mnonstop
Southwest Logo
6:55 pm - 7:20 pm
PIT
-
MDW
1h 25mnonstop
$219Southwest
Wed, Nov 4 - Wed, Nov 11
Southwest Logo
8:15 am - 10:45 am
MDW
-
PIT
1h 30mnonstop
Southwest Logo
8:45 am - 9:15 am
PIT
-
MDW
1h 30mnonstop
$225Southwest
Wed, Jul 1 - Wed, Jul 8
Southwest Logo
7:50 am - 10:20 am
MDW
-
PIT
1h 30mnonstop
Southwest Logo
6:45 am - 12:25 pm
PIT
-
MDW
6h 40m
1 stop
$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, Saturday is the cheapest day to fly on average and Friday is the most expensive. Flying from Pittsburgh back to Chicago Midway Airport, the best deals are generally found on Wednesday, with Monday 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 $260, prices are generally cheapest when you fly direct.

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.

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.

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 9% 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 5 days, the lowest price for a flight from Chicago Midway Airport to Pittsburgh was $69 for a one-way ticket and $191 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 Boeing 737 MAX 8 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 $247 or less one-way and $240 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.
7.9
SouthwestOverall score based on 4235 reviews
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
Airline reviews

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

10.0 ExcellentAnonymous, Jun 2026
OKC - LAS
Read more Southwest reviews

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

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

Information on your arrival and departure airports