MDW - PIT

$49 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 12/3. 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
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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

Thu, Dec 4 - Mon, Dec 8
Southwest Logo
2:30 pm - 9:55 pmMDW-PIT
6h 25m2 stops
Southwest Logo
6:45 pm - 7:15 pmPIT-MDW
1h 30mnonstop
$112Southwest
Find Deal
Thu, Dec 4 - Mon, Dec 8
Southwest Logo
2:30 pm - 9:55 pmMDW-PIT
6h 25m2 stops
Southwest Logo
4:05 pm - 9:05 pmPIT-MDW
6h 00m1 stop
$122Southwest
Find Deal
Thu, Dec 4 - Mon, Dec 8
Southwest Logo
2:30 pm - 9:55 pmMDW-PIT
6h 25m2 stops
Southwest Logo
5:30 am - 12:35 pmPIT-MDW
8h 05m2 stops
$127Southwest
Find Deal
Sat, Jan 17 - Sun, Jan 18
Delta Logo
5:00 pm - 11:46 pmMDW-PIT
5h 46m1 stop
Delta Logo
6:00 am - 10:34 amPIT-MDW
5h 34m1 stop
$177Delta
Find Deal
Thu, Nov 20 - Mon, Nov 24
Multiple Airlines Logo
6:20 am - 7:21 amMDW-PIT
24h 01m1 stop
Multiple Airlines Logo
10:42 pm - 11:42 amPIT-MDW
14h 00m1 stop
$191Multiple Airlines
Find Deal
Wed, Nov 26 - Wed, Dec 3
Multiple Airlines Logo
5:30 pm - 8:19 amMDW-PIT
13h 49m1 stop
Multiple Airlines Logo
10:42 pm - 1:01 pmPIT-MDW
15h 19m1 stop
$206Multiple Airlines
Find Deal
Mon, Nov 24 - Mon, Dec 1
Multiple Airlines Logo
5:47 pm - 8:19 amMDW-PIT
13h 32m1 stop
Multiple Airlines Logo
10:42 pm - 1:01 pmPIT-MDW
15h 19m1 stop
$209Multiple Airlines
Find Deal
Mon, Dec 1 - Wed, Dec 3
Southwest Logo
10:10 pm - 12:30 amMDW-PIT
1h 20mnonstop
Southwest Logo
2:00 pm - 2:30 pmPIT-MDW
1h 30mnonstop
$231Southwest
Find Deal
Wed, Jan 28 - Sun, Feb 1
Delta Logo
10:46 am - 6:33 pmMDW-PIT
6h 47m1 stop
Delta Logo
10:24 am - 12:48 pmPIT-MDW
3h 24m1 stop
$261Delta
Find Deal
Thu, Nov 27 - Thu, Dec 4
Delta Logo
5:34 pm - 12:21 amMDW-PIT
5h 47m1 stop
Delta Logo
1:00 pm - 6:00 pmPIT-MDW
6h 00m1 stop
$288Delta
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
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 $112 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
September
Cheapest • 64% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$112
Overall average: $701
Southwest
Thu 12/4Mon 12/8
MDW - PIT • 2 stops
Cheapest non-stop
$231
Typical prices: $552-$850
Southwest
Mon 12/1Wed 12/3
MDW - PIT • Non-stop
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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!
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 Sunday is the most expensive. Flying from Pittsburgh back to Chicago Midway Airport, the best deals are generally found on Tuesday, with Saturday 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 September, where tickets cost $114 (return) on average. On the other hand, the most expensive months are December and May, where the average cost of round-trip tickets is $701 and $527 respectively.

Expert advice

Expert advice for your flight from Midway to Pittsburgh

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
MDW

Midway offers a user-friendly experience with a compact terminal, making it easy to navigate and access various dining and shopping options.

Read more about MDWby Stefanie Waldek
PIT

The 28X Airport Flyer bus is the most budget-friendly option to reach downtown Pittsburgh, taking about 45 minutes from PIT.

Read more about PITby Matt Meltzer
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek

Stefanie Waldek

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

Matt Meltzer

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 seasonFebruary
Cheapest flight$49
Best time to beat the crowds with an average 57% drop in price.
Most popular time to fly with an average 67% 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 $49 for a one-way ticket and $112 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?

    Only American Airlines offers 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 737-800 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 $48 or less one-way and $156 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 4245 reviews
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

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

Information on your arrival and departure airports

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