MDW - PIT

$39 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 8/4. 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

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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Flights 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 7 - Mon, Aug 11
Southwest Logo
5:25 pm - 7:45 pmMDW-PIT
1h 20mnonstop
Southwest Logo
6:25 am - 6:50 amPIT-MDW
1h 25mnonstop
$77Southwest
Find Deal
Thu, Aug 7 - Mon, Aug 11
Southwest Logo
1:15 pm - 3:40 pmMDW-PIT
1h 25mnonstop
Southwest Logo
4:00 pm - 8:25 pmPIT-MDW
5h 25m1 stop
$87Southwest
Find Deal
Sat, Sep 13 - Tue, Sep 16
Delta Logo
5:59 pm - 10:36 pmMDW-PIT
3h 37m1 stop
Delta Logo
6:05 pm - 9:44 pmPIT-MDW
4h 39m1 stop
$198Delta
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Fri, Jul 11 - Sun, Jul 13
Frontier Logo
8:35 am - 6:40 pmMDW-PIT
9h 05m1 stop
Frontier Logo
9:56 am - 3:06 pmPIT-MDW
6h 10m1 stop
$200Frontier
Find Deal
Thu, Jun 26 - Mon, Jun 30
Frontier Logo
9:12 pm - 6:00 pmMDW-PIT
19h 48m1 stop
Frontier Logo
3:49 pm - 11:51 pmPIT-MDW
9h 02m1 stop
$210Frontier
Find Deal
Tue, Jul 29 - Tue, Aug 5
Delta Logo
6:20 pm - 11:59 pmMDW-PIT
4h 39m1 stop
Delta Logo
11:05 am - 5:39 pmPIT-MDW
7h 34m1 stop
$213Delta
Find Deal
Fri, Jul 18 - Sun, Jul 20
Logo
8:03 am - 3:12 pmMDW-PIT
6h 09m1 stop
Logo
6:30 am - 9:41 amPIT-MDW
28h 11m2 stops
$270
Find Deal
Sun, Jul 13 - Sun, Jul 20
Logo
11:37 am - 11:39 pmMDW-PIT
11h 02m1 stop
Logo
6:30 am - 9:41 amPIT-MDW
28h 11m2 stops
$276
Find Deal
Mon, Jul 21 - Thu, Jul 24
Allegiant Air Logo
8:03 am - 3:12 pmMDW-PIT
6h 09m1 stop
Allegiant Air Logo
6:00 pm - 2:04 pmPIT-MDW
21h 04m2 stops
$358Allegiant Air
Find Deal
Fri, Jul 4 - Sun, Jul 6
Allegiant Air Logo
8:03 am - 3:12 pmMDW-PIT
6h 09m1 stop
Allegiant Air Logo
3:20 pm - 9:41 amPIT-MDW
19h 21m2 stops
$417Allegiant Air
Find Deal
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
Useful Info

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 Sunday is the most expensive. Flying from Pittsburgh back to Chicago Midway Airport, the best deals are generally found on Wednesday, 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 February, where tickets cost $137 (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.

Find deals

Good to know

Low seasonFebruary
High seasonMay
Cheapest flight$39
Best time to beat the crowds with an average 63% drop in price.
Most popular time to fly with an average 43% 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 $39 for a one-way ticket and $77 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 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 $132 or less one-way and $199 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

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 4278 reviews
8.6Crew
7.1Food
8.2Boarding
8.0Comfort
7.6Entertainment
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

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)

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