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 5/20. 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
$182
Typical prices: $538-$436
Southwest
Wed 5/27Thu 5/28
MDW - PIT • 2 stops
Cheapest non-stop
$192
Southwest
Tue 5/19Tue 5/19
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
Cheapest • from $182 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 1h 23m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Most punctual • 85% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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
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

Wed, May 27 - Thu, May 28
Southwest Logo
10:10 am - 5:55 pm
MDW
-
PIT
6h 45m
2 stops
Southwest Logo
8:05 pm - 10:45 pm
PIT
-
MDW
3h 40m
1 stop
$182Southwest
Sat, May 23 - Sat, May 30
Southwest Logo
5:25 pm - 11:00 pm
MDW
-
PIT
4h 35m
1 stop
Southwest Logo
4:00 pm - 4:30 pm
PIT
-
MDW
1h 30mnonstop
$187Southwest
Tue, May 26 - Tue, Jun 2
Southwest Logo
8:15 am - 12:55 pm
MDW
-
PIT
3h 40m
1 stop
Southwest Logo
6:25 am - 3:45 pm
PIT
-
MDW
10h 20m
2 stops
$188Southwest
Tue, May 19 - Tue, May 19
Southwest Logo
7:50 am - 10:15 am
MDW
-
PIT
1h 25mnonstop
Southwest Logo
7:10 pm - 7:40 pm
PIT
-
MDW
1h 30mnonstop
$192Southwest
Sat, May 23 - Sat, May 30
Delta Logo
5:10 pm - 12:45 am
MDW
-
PIT
6h 35m
1 stop
Delta Logo
6:40 am - 1:19 pm
PIT
-
MDW
7h 39m
1 stop
$197Delta
Mon, May 18 - Wed, May 20
Southwest Logo
7:40 am - 10:00 am
MDW
-
PIT
1h 20mnonstop
Southwest Logo
6:40 am - 3:50 pm
PIT
-
MDW
10h 10m
2 stops
$198Southwest
Tue, May 19 - Tue, May 19
Southwest Logo
8:00 am - 12:50 pm
MDW
-
PIT
3h 50m
1 stop
Southwest Logo
7:10 pm - 7:40 pm
PIT
-
MDW
1h 30mnonstop
$202Southwest
Tue, May 19 - Tue, May 19
Southwest Logo
10:10 am - 5:55 pm
MDW
-
PIT
6h 45m
2 stops
Southwest Logo
7:10 pm - 7:40 pm
PIT
-
MDW
1h 30mnonstop
$207Southwest
Tue, May 19 - Wed, May 27
Delta Logo
1:22 pm - 6:49 pm
MDW
-
PIT
4h 27m
1 stop
Delta Logo
6:30 am - 8:43 am
PIT
-
MDW
3h 13m
1 stop
$208Delta
Thu, May 21 - Mon, May 25
Southwest Logo
7:40 am - 10:00 am
MDW
-
PIT
1h 20mnonstop
Southwest Logo
8:40 am - 9:10 am
PIT
-
MDW
1h 30mnonstop
$212Southwest
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.

How much is a round-trip flight from Chicago Midway Airport to Pittsburgh?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Pittsburgh departing in May.

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 Wednesday, with Sunday being the most expensive.

What is the cheapest month to fly from Chicago Midway Airport to Pittsburgh?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Pittsburgh, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Pittsburgh is February, where tickets cost $0 (return) on average. On the other hand, the most expensive months are March and May, where the average cost of round-trip tickets is $644 and $533 respectively.

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 $354, 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 66% drop in price.
Most popular time to fly with an average 60% 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 $182 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 $171 or less one-way and $343 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 4314 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.0Food
7.5Entertainment
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

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

Information on your arrival and departure airports