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PIT - MDW

$59 Find cheap flights from Pittsburgh to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Pittsburgh to Midway departing on 6/19. 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
0 bags
Wed 7/10
Wed 7/17

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Pittsburgh to Chicago, 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 Pittsburgh to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 42,898,604 times on KAYAK, and here is why:

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

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

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Cheap flight deals from Pittsburgh to Midway (PIT-MDW)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Pittsburgh to Midway 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 and deals for you by selecting your travel dates.
Choose your dates
5:49 pm - 10:58 pmPIT-MDW
6h 09m1 stop
7:30 am - 4:59 pmMDW-PIT
8h 29m1 stop
$138Frontier
Find Deal
Wed, Jun 26 - Mon, Jul 1
5:49 pm - 10:58 pmPIT-MDW
6h 09m1 stop
12:57 pm - 9:22 pmMDW-PIT
7h 25m1 stop
$139Frontier
Find Deal
Wed, Jun 26 - Fri, Jun 28
5:53 pm - 9:25 pmPIT-MDW
4h 32m1 stop
10:20 pm - 7:15 amMDW-PIT
7h 55m1 stop
$140Frontier
Find Deal
Tue, Jul 9 - Tue, Jul 16
8:05 am - 1:28 pmPIT-MDW
6h 23m1 stop
10:20 pm - 7:15 amMDW-PIT
7h 55m1 stop
$151Frontier
Find Deal
Mon, Jul 15 - Tue, Jul 16
5:53 pm - 9:25 pmPIT-MDW
4h 32m1 stop
1:07 pm - 9:58 pmMDW-PIT
7h 51m1 stop
$154Frontier
Find Deal
Tue, Jul 23 - Thu, Jul 25
2:08 pm - 5:03 pmPIT-MDW
3h 55m1 stop
5:43 pm - 10:56 pmMDW-PIT
4h 13m1 stop
$166Delta
Find Deal
Sat, Jul 13 - Tue, Jul 16
6:15 am - 8:49 amPIT-MDW
3h 34m1 stop
1:25 pm - 5:39 pmMDW-PIT
3h 14m1 stop
$207Delta
Find Deal
Wed, Jul 3 - Mon, Jul 8
6:25 am - 8:40 amPIT-MDW
3h 15m1 stop
1:08 pm - 7:44 pmMDW-PIT
5h 36m1 stop
$238Delta
Find Deal
Fri, Sep 20 - Mon, Sep 23
6:22 am - 8:38 amPIT-MDW
3h 16m1 stop
5:43 pm - 10:56 pmMDW-PIT
4h 13m1 stop
$240Delta
Find Deal
Sun, Jul 28 - Tue, Jul 30
6:50 am - 8:18 pmPIT-MDW
14h 28m2 stops
12:03 pm - 11:16 pmMDW-PIT
10h 13m1 stop
Fri, Jun 21 - Mon, Jun 24

Flights from Pittsburgh to Midway - Travel Insights & Trends

Get data-powered insights and trends into flights from Pittsburgh to Midway 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 Pittsburgh to Chicago Midway Airport?

The average price of all flights from Pittsburgh to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
For Pittsburgh to Chicago Midway Airport, Sunday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago Midway Airport back to Pittsburgh, the best deals are generally found on Monday, with Friday being the most expensive.

Which airlines provide the cheapest flights from Pittsburgh to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Pittsburgh to Chicago Midway Airport found by KAYAK users in the last 72 hours was for $138 on Frontier, followed by Delta ($166). One-way flight deals have also been found from as low as $59 on Frontier and from $78 on Delta.

How many flights are there between Pittsburgh and Chicago Midway Airport per day?

Each day, there are between 3 and 7 nonstop flights that take off from Pittsburgh and land in Chicago Midway Airport, with an average flight time of 1h 25m. The most common departure time is 6:00 am and most flights take off in the morning. Each week, there are 34 flights. The most frequent day of departure is Friday, when 21% of all weekly flights depart. The fewest flights depart on a Sunday.

Which cabin class options are there for flights between Pittsburgh and Chicago Midway Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

What’s the earliest departure time from Pittsburgh to Chicago Midway Airport?

Early birds can take the earliest flight from Pittsburgh at 6:20 am and will be landing in Chicago Midway Airport at 6:45 am.

What’s the latest departure time from Pittsburgh to Chicago Midway Airport?

If you prefer to fly at night, the latest flight from Pittsburgh to Chicago Midway Airport jets off at 9:20 pm and lands at 9:45 pm.

Good to know

Low season

April

High season

August

Cheapest flight

$59
Best time to beat the crowds with an average 45% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from Pittsburgh to Chicago Midway Airport

When to book flights from Pittsburgh to Midway

Are your dates flexible? Find out the best times to travel from Pittsburgh to Midway 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 Pittsburgh to Chicago Midway Airport flights

  • What is the cheapest flight from Pittsburgh to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Pittsburgh to Chicago Midway Airport was $59 for a one-way ticket and $138 for a round-trip.

  • Do I need a passport to fly between Pittsburgh and Chicago Midway Airport?

    No, a passport isn't needed to fly from Pittsburgh to Chicago Midway Airport. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Pittsburgh to Chicago Midway Airport?

    On your way to Chicago Midway Airport, you’ll fly out from Pittsburgh. You’ll be landing at Chicago Midway.

  • Which airlines offer Wi-Fi service onboard planes from Pittsburgh to Chicago Midway Airport?

    Only American Airlines offers inflight Wi-Fi service on the Pittsburgh to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from Pittsburgh to Chicago Midway Airport?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Pittsburgh to Chicago Midway Airport flight route.

  • On which days can I fly direct from Pittsburgh to Chicago Midway Airport?

    There are nonstop flights from Pittsburgh to Chicago Midway Airport on a daily basis.

  • How does KAYAK find such low prices on flights from Pittsburgh to Chicago Midway Airport?

    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 Pittsburgh to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Pittsburgh to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Pittsburgh 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 Pittsburgh to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to Pittsburgh with another airline. Booking your flights between Pittsburgh and MDW 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 Pittsburgh to Chicago Midway Airport?

    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 Chicago Midway Airport from Pittsburgh up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Pittsburgh to Chicago Midway Airport?

Find which airlines fly direct from Pittsburgh to Midway, which days they fly and book direct flights.

Nonstop departures

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

Nonstop returns

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
See more direct flights

Top airline flying from Pittsburgh to Midway

 
See real verified KAYAK customer reviews for airlines flying from Pittsburgh to Chicago. 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 Pittsburgh to Midway? 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
DeltaOverall score based on 10295 reviews
8.2Boarding
8.0Entertainment
8.6Crew
7.9Comfort
7.4Food
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Book cheap flights from Pittsburgh to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Pittsburgh to Chicago found on KAYAK in the last 72 hours.
6/19Wed
1 stopFrontier
6h 09mPIT-MDW
$59
6/18Tue
1 stopFrontier
5h 26mPIT-MDW
$64
8/14Wed
1 stopFrontier
4h 57mPIT-MDW
$66
6/17Mon
1 stopFrontier
6h 09mPIT-MDW
$67
7/23Tue
1 stopFrontier
4h 32mPIT-MDW
$72
7/1Mon
1 stopDelta
3h 34mPIT-MDW
$78
7/25Thu
1 stopDelta
3h 07mPIT-MDW
$88
7/29Mon
1 stopDelta
4h 33mPIT-MDW
$119
7/24Wed
1 stopDelta
6h 12mPIT-MDW
$139
7/1Mon
2 stops
13h 18mPIT-MDW
$160

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Last minute flights from Pittsburgh to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Pittsburgh to Chicago that are departing in the next 10 days.
6/15Sat
multi-stopFrontier
8h 47mPIT-MDW
6/18Tue
multi-stopFrontier
8h 03mMDW-PIT
$158
6/15Sat
multi-stopFrontier
8h 47mPIT-MDW
6/17Mon
multi-stopFrontier
7h 25mMDW-PIT
$179
6/14Fri
multi-stopFrontier
6h 28mPIT-MDW
6/16Sun
multi-stopFrontier
8h 26mMDW-PIT
$187
6/14Fri
multi-stopFrontier
6h 28mPIT-MDW
6/16Sun
multi-stopFrontier
8h 26mMDW-PIT
$191
6/12Wed
multi-stopFrontier
6h 09mPIT-MDW
6/15Sat
multi-stopFrontier
8h 17mMDW-PIT
$198
6/14Fri
multi-stopFrontier
6h 28mPIT-MDW
6/15Sat
multi-stopFrontier
8h 17mMDW-PIT
$208
6/14Fri
multi-stopFrontier
6h 28mPIT-MDW
6/16Sun
multi-stopFrontier
8h 26mMDW-PIT
$214
6/13Thu
multi-stopFrontier
14h 51mPIT-MDW
6/15Sat
multi-stopFrontier
8h 17mMDW-PIT
$245

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Pittsburgh - Chicago Midway Airport Flights

Departure:

Pittsburgh (PIT)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Pittsburgh

Cabin classes:

$675