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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 5/14. 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
Sat 4/27
Sat 5/4

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 46,342,885 times on KAYAK, and here is why:

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Cheap flight deals from Pittsburgh to Midway

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
1:41 pm - 10:05 pmPIT-MDW
9h 24m1 stop
9:29 pm - 11:36 amMDW-PIT
13h 07m1 stop
$116Frontier
Find Deal
Tue, May 7 - Sat, May 11
1:41 pm - 10:05 pmPIT-MDW
9h 24m1 stop
9:29 pm - 11:36 amMDW-PIT
13h 07m1 stop
$121Frontier
Find Deal
Tue, May 7 - Sat, May 11
1:27 pm - 7:40 pmPIT-MDW
7h 13m1 stop
5:01 am - 7:58 pmMDW-PIT
13h 57m1 stop
$128Frontier
Find Deal
Thu, May 16 - Sun, May 19
9:48 am - 8:30 pmPIT-MDW
11h 42m1 stop
10:01 pm - 7:58 pmMDW-PIT
20h 57m1 stop
$152Frontier
Find Deal
Thu, May 16 - Sat, May 18
1:27 pm - 7:40 pmPIT-MDW
7h 13m1 stop
10:33 pm - 10:58 amMDW-PIT
11h 25m1 stop
$153Frontier
Find Deal
Thu, May 30 - Sat, Jun 1
6:05 am - 8:50 amPIT-MDW
3h 45m1 stop
5:45 pm - 10:56 pmMDW-PIT
4h 11m1 stop
$156Delta
Find Deal
Sat, Apr 27 - Sat, Apr 27
6:05 am - 8:50 amPIT-MDW
3h 45m1 stop
5:45 pm - 10:56 pmMDW-PIT
4h 11m1 stop
$157Delta
Find Deal
Wed, Apr 24 - Sat, Apr 27
6:05 am - 8:50 amPIT-MDW
3h 45m1 stop
6:00 pm - 10:56 pmMDW-PIT
3h 56m1 stop
$158Delta
Find Deal
Tue, Apr 23 - Wed, Apr 24
4:35 pm - 10:14 pmPIT-MDW
6h 39m1 stop
9:30 am - 1:21 pmMDW-PIT
2h 51m1 stop
$197Delta
Find Deal
Tue, Apr 30 - Fri, May 3
5:20 am - 2:21 pmPIT-MDW
10h 01m1 stop
7:34 pm - 8:03 pmMDW-PIT
23h 29m1 stop
Tue, Apr 9 - Tue, Apr 9

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, Saturday 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 Thursday 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 $116 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 29m. The most common departure time is 7:00 am and most flights take off in the morning. Each week, there are 35 flights. The most frequent day of departure is Monday, when 20% of all weekly flights depart. The fewest flights depart on a Wednesday.

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.

How long does a flight from Pittsburgh to Chicago Midway Airport take?

Direct flights take on average 3h 05m to travel the 400 miles between Pittsburgh and Chicago Midway Airport.

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

Early birds can take the earliest flight from Pittsburgh at 5:55 am and will be landing in Chicago Midway Airport at 6:30 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 9:25 pm and lands at 9:50 pm.

Good to know

High season

November

Cheapest flight

$50
Most popular time to fly with an average 1% 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 $116 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

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 KAYAK reviews.
8.0
DeltaOverall score based on 11402 reviews
75food
86crew
82boarding
80entertainment
81overall
79comfort
Airline reviews

Carly the flight attendant was extremely helpful and very accommodating to passengers on the flight from what I noticed. Couldn't be more satisfied with the service and assistance from Delta's flight attendant, Thanks again Carly!!

Read more about Delta

Carly the flight attendant was extremely helpful and very accommodating to passengers on the flight from what I noticed. Couldn't be more satisfied with the service and assistance from Delta's flight attendant, Thanks again Carly!!

I didn’t not like that I could not select my seat and ended up with the worse seat.

I didn’t like that I could not select my seat and was assigned a seat when I checked in at LAX

Delta did an awful job w logistics at DTW. Missed connection. We were there an hour early. SUCKED

Inflight entertainment stopped working as we taxi to runway and never worked again until landing and taxi to gate. Grrrr

Had to run to make it only to have the flight delayed to wait for all the late connectors Second drink service skipped up

Boarding was a sh!t show. JFK BOARDING was awful. The agent called three sections at a time Clogging the area then yelling at people to not block the walk way. How are you going to call delta one , premium select and comfort plus at once and the yell at highest paying passengers. Need to do a lot better and the flight attendants in the galley need to understand that their voices travel. They were talking about others and everyone in the cabin heard them

Uncomfortable seats on 14 hour flight. Mediocre food. On time and great crew.

MSP to Atlanta was much better than Atlanta to St. Kitts. Paid $180 each for myself and wife for Delta comfort from Atlanta to St. Kitts. Seats were more narrow and obviously old and worn out. Tailbone is killing me. Seat would not recline. Seats behind reclined and we were not an exit row or in front of an exit row. Entertainment did not work in that the movie jumped forward and back and there was no audio. The plug in the arm rest was loose. Flight attendant tried “resetting” the video for my seat but no good. She never checked back. Someone else near me had the same issue. Touch screen was unresponsive. No where near as comfortable as MSP to Atlanta flight. 3 plus hrs. flight time without the basic amenities and not even remotely close to comfortable but paid for Comfort plus. I will be very disappointed if I have the same on my return “Comfort Plus” flight St. Kitts to Atlanta. At the very least my wife and I should be refunded for round trip “Comfort Plus” charges. Please feel free to contact me directly for more details.

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

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.
5/14Tue
1 stopFrontier
9h 24mPIT-MDW
$50
4/16Tue
1 stopFrontier
9h 24mPIT-MDW
$58
5/20Mon
1 stopFrontier
5h 18mPIT-MDW
$60
4/23Tue
1 stopFrontier
9h 24mPIT-MDW
$61
6/26Wed
1 stopFrontier
4h 57mPIT-MDW
$70
4/27Sat
1 stopDelta
4h 49mPIT-MDW
$78
4/26Fri
1 stopDelta
4h 49mPIT-MDW
$79
4/21Sun
1 stopDelta
3h 45mPIT-MDW
$99
4/9Tue
1 stop
15h 58mPIT-MDW
$101
5/9Thu
1 stopDelta
4h 01mPIT-MDW
$119

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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.
4/2Tue
multi-stop
10h 01mPIT-MDW
4/5Fri
multi-stop
22h 20mMDW-PIT
$445
3/30Sat
multi-stopDelta
3h 41mPIT-MDW
3/30Sat
multi-stopDelta
3h 51mMDW-PIT
$450
4/2Tue
multi-stopDelta
5h 43mPIT-MDW
4/5Fri
multi-stopDelta
4h 46mMDW-PIT
$476
4/1Mon
multi-stopDelta
6h 27mPIT-MDW
4/6Sat
multi-stopDelta
5h 35mMDW-PIT
$478
4/1Mon
multi-stop
10h 45mPIT-MDW
4/4Thu
multi-stop
22h 41mMDW-PIT
$496
3/29Fri
multi-stopDelta
5h 04mPIT-MDW
3/31Sun
multi-stopDelta
3h 05mMDW-PIT
$506
4/2Tue
multi-stop
10h 01mPIT-MDW
4/5Fri
multi-stop
13h 18mMDW-PIT
$519
4/1Mon
multi-stop
10h 45mPIT-MDW
4/4Thu
multi-stop
13h 59mMDW-PIT
$546
3/30Sat
multi-stop
8h 23mPIT-MDW
3/30Sat
multi-stop
13h 10mMDW-PIT
$698
3/30Sat
multi-stopDelta
5h 04mPIT-MDW
3/30Sat
multi-stopDelta
5h 02mMDW-PIT
$934

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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