MDW - PIT

$101 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 5/15. 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

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

 
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.

Recent round-trip flight deals from Midway to Pittsburgh

KAYAK's recommended round-trip deals from the most popular airlines that fly from Midway to Pittsburgh.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
10:20 am - 12:40 pmMDW-PIT
1h 20mnonstop
Southwest Logo
1:05 pm - 1:35 pmPIT-MDW
1h 30mnonstop
$235Southwest
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Tue, May 20 - Tue, May 27
Southwest Logo
10:20 am - 12:40 pmMDW-PIT
1h 20mnonstop
Southwest Logo
4:00 pm - 7:40 pmPIT-MDW
4h 40m1 stop
$245Southwest
Find Deal
Tue, May 20 - Tue, May 27
Southwest Logo
9:10 am - 6:45 pmMDW-PIT
8h 35m2 stops
Southwest Logo
6:45 am - 7:15 amPIT-MDW
1h 30mnonstop
$250Southwest
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Tue, May 20 - Tue, May 27
Delta Logo
6:25 pm - 10:53 pmMDW-PIT
3h 28m1 stop
Delta Logo
11:01 am - 5:40 pmPIT-MDW
7h 39m1 stop
$255Delta
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Tue, Jun 3 - Tue, Jun 10
Southwest Logo
9:10 am - 6:45 pmMDW-PIT
8h 35m2 stops
Southwest Logo
4:00 pm - 7:40 pmPIT-MDW
4h 40m1 stop
$260Southwest
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Tue, May 20 - Tue, May 27
Southwest Logo
7:55 am - 10:15 amMDW-PIT
1h 20mnonstop
Southwest Logo
2:15 pm - 2:45 pmPIT-MDW
1h 30mnonstop
$265Southwest
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Fri, May 30 - Mon, Jun 2
Delta Logo
9:20 am - 4:08 pmMDW-PIT
5h 48m1 stop
Delta Logo
6:25 am - 8:40 amPIT-MDW
3h 15m1 stop
$270Delta
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Wed, May 21 - Mon, May 26
Southwest Logo
1:25 pm - 10:00 pmMDW-PIT
7h 35m2 stops
Southwest Logo
6:00 am - 2:35 pmPIT-MDW
9h 35m2 stops
$271Southwest
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Tue, May 20 - Tue, May 27
Delta Logo
6:00 am - 12:50 pmMDW-PIT
5h 50m1 stop
Delta Logo
11:01 am - 5:12 pmPIT-MDW
7h 11m1 stop
$285Delta
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Sat, Jun 14 - Sat, Jun 21
Logo
8:36 pm - 11:54 pmMDW-PIT
26h 18m2 stops
Logo
6:30 am - 2:03 pmPIT-MDW
32h 33m2 stops
$324
Find Deal
Fri, Jun 6 - Sun, Jun 8
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 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 May, where tickets cost $132 (return) on average. On the other hand, the most expensive months are December and October, where the average cost of round-trip tickets is $701 and $504 respectively.

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Good to know

Low seasonFebruary
High seasonNovember
Cheapest flight$101
Best time to beat the crowds with an average 60% drop in price.
Most popular time to fly with an average 23% 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 $101 for a one-way ticket and $235 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 Embraer 175 (Enhanced Winglets) 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 $117 or less one-way and $240 or less round-trip.

Prefer to fly direct from Chicago Midway Airport 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
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 4294 reviews
8.2Boarding
7.1Food
8.0Comfort
7.6Entertainment
8.6Crew
Airline reviews

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

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

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.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

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

Information on your arrival and departure airports

Pittsburgh (PIT)
Chicago Midway Airport (MDW)

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