Find flights
Deals
Insights
When to book
FAQs & Tips
Direct Flights
Airlines

PIT - MDW

Find cheap flights from Pittsburgh to Chicago Midway Airport from $50

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 6/12. 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
Thu 6/6
Thu 6/13

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 43,707,506 times on KAYAK, and here is why:

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

Track pricesNot ready to book? Create a price alert for when prices drop.

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

Bundle and saveSave money when you bundle your flight + hotel.

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
12:57 pm - 9:22 pmMDW-PIT
7h 25m1 stop
$100Frontier
Find Deal
Wed, Jun 5 - Wed, Jun 12
12:03 pm - 7:55 pmPIT-MDW
8h 52m1 stop
10:16 pm - 7:19 amMDW-PIT
8h 03m1 stop
$109Frontier
Find Deal
Tue, Jun 4 - Tue, Jun 11
6:04 pm - 9:53 pmPIT-MDW
4h 49m1 stop
12:09 pm - 9:38 pmMDW-PIT
8h 29m1 stop
$111Frontier
Find Deal
Wed, May 22 - Wed, May 29
5:49 pm - 10:58 pmPIT-MDW
6h 09m1 stop
12:57 pm - 9:22 pmMDW-PIT
7h 25m1 stop
$123Frontier
Find Deal
Wed, Jun 5 - Fri, Jun 7
5:58 pm - 9:55 pmPIT-MDW
4h 57m1 stop
6:00 am - 7:50 pmMDW-PIT
12h 50m1 stop
$127Frontier
Find Deal
Wed, Aug 14 - Thu, Aug 15
1:13 pm - 5:59 pmPIT-MDW
5h 46m1 stop
1:10 pm - 5:20 pmMDW-PIT
3h 10m1 stop
$156Delta
Find Deal
Tue, Jul 23 - Wed, Aug 7
6:10 pm - 9:47 pmPIT-MDW
4h 37m1 stop
10:11 am - 5:04 pmMDW-PIT
5h 53m1 stop
$197Delta
Find Deal
Sat, Aug 10 - Sat, Aug 17
6:00 pm - 9:45 amPIT-MDW
16h 45m1 stop
1:08 pm - 11:33 pmMDW-PIT
9h 25m1 stop
$328Allegiant Air
Find Deal
Sat, May 25 - Mon, May 27
6:00 pm - 9:45 amPIT-MDW
16h 45m1 stop
8:34 am - 12:59 amMDW-PIT
15h 25m2 stops
Sat, May 25 - Mon, May 27
5:30 am - 7:43 pmPIT-MDW
15h 13m2 stops
2:14 pm - 1:34 amMDW-PIT
10h 20m2 stops
Mon, Jun 3 - Fri, Jun 7

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 $100 on Frontier, followed by Delta ($156). One-way flight deals have also been found from as low as $50 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 2 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 7:00 am and most flights take off in the morning. Each week, there are 37 flights. The most frequent day of departure is Friday, when 19% of all weekly flights depart. The fewest flights depart on a Saturday.

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

$50
Best time to beat the crowds with an average 46% drop in price.
Most popular time to fly with an average 12% 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 $50 for a one-way ticket and $100 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 10810 reviews
8.6Crew
7.9Comfort
8.0Entertainment
8.2Boarding
7.4Food
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

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.
6/12Wed
1 stopFrontier
6h 09mPIT-MDW
$50
6/5Wed
1 stopFrontier
6h 21mPIT-MDW
$55
5/29Wed
1 stopFrontier
4h 49mPIT-MDW
$58
5/31Fri
1 stopFrontier
5h 02mPIT-MDW
$73
6/25Tue
1 stopFrontier
5h 26mPIT-MDW
$74
6/1Sat
1 stopDelta
4h 44mPIT-MDW
$78
10/18Fri
1 stopDelta
3h 30mPIT-MDW
$149
6/27Thu
1 stopDelta
3h 55mPIT-MDW
$154
6/3Mon
2 stops
15h 13mPIT-MDW
$177
5/24Fri
1 stopDelta
4h 01mPIT-MDW
$212

Search by stops

Search by airline

Search by price

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.
5/12Sun
multi-stopFrontier
24h 02mPIT-MDW
5/16Thu
multi-stopFrontier
13h 59mMDW-PIT
$163
5/12Sun
multi-stopFrontier
24h 02mPIT-MDW
5/19Sun
multi-stopFrontier
13h 57mMDW-PIT
$303
5/9Thu
multi-stopFrontier
9h 22mPIT-MDW
5/11Sat
multi-stopFrontier
13h 07mMDW-PIT
$327
5/11Sat
multi-stopDelta
5h 37mPIT-MDW
5/15Wed
multi-stopDelta
5h 03mMDW-PIT
$456
5/11Sat
multi-stopDelta
6h 22mPIT-MDW
5/12Sun
multi-stopDelta
3h 09mMDW-PIT
$471
5/10Fri
multi-stopDelta
5h 50mPIT-MDW
5/12Sun
multi-stopDelta
7h 27mMDW-PIT
$486
5/8Wed
multi-stopDelta
4h 01mPIT-MDW
5/14Tue
multi-stopDelta
3h 09mMDW-PIT
$536
5/9Thu
multi-stop
25h 46mPIT-MDW
5/13Mon
multi-stop
26h 10mMDW-PIT
$541
5/9Thu
multi-stopDelta
4h 44mPIT-MDW
5/14Tue
multi-stopDelta
2h 49mMDW-PIT
$544
5/11Sat
multi-stopDelta
4h 44mPIT-MDW
5/15Wed
multi-stopDelta
19h 54mMDW-PIT
$550

Search by stops

Search by airline

Search by price

Pittsburgh - Chicago Midway Airport Flights

Departure:

Pittsburgh (undefined)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Pittsburgh

Cabin classes:

$675