PIT - MDW

$49 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 10/15. 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
1 adult, Economy

KAYAK searches 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
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Booking Insights
Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Pittsburgh to Midway

Tue, Oct 14 - Tue, Oct 21
Southwest Logo
6:20 am - 6:50 amPIT-MDW
1h 30mnonstop
Southwest Logo
1:25 pm - 3:45 pmMDW-PIT
1h 20mnonstop
$97Southwest
Find Deal
Tue, Oct 14 - Tue, Oct 21
Southwest Logo
6:20 am - 6:50 amPIT-MDW
1h 30mnonstop
Southwest Logo
5:35 am - 12:25 pmMDW-PIT
5h 50m1 stop
$107Southwest
Find Deal
Tue, Oct 14 - Tue, Oct 21
Southwest Logo
1:10 pm - 7:10 pmPIT-MDW
7h 00m2 stops
Southwest Logo
8:45 pm - 11:05 pmMDW-PIT
1h 20mnonstop
$112Southwest
Find Deal
Wed, Oct 15 - Sat, Oct 18
Southwest Logo
4:00 pm - 4:25 pmPIT-MDW
1h 25mnonstop
Southwest Logo
6:30 am - 3:10 pmMDW-PIT
7h 40m1 stop
$113Southwest
Find Deal
Fri, Sep 26 - Sun, Sep 28
Frontier Logo
9:34 am - 9:51 amPIT-MDW
25h 17m1 stop
Frontier Logo
8:06 am - 2:36 pmMDW-PIT
5h 30m1 stop
$159Frontier
Find Deal
Wed, Oct 15 - Sat, Oct 18
Delta Logo
1:00 pm - 6:25 pmPIT-MDW
6h 25m1 stop
Delta Logo
10:35 am - 5:33 pmMDW-PIT
5h 58m1 stop
$177Delta
Find Deal
Tue, Oct 28 - Tue, Nov 4
 Logo
7:12 am - 11:25 pmPIT-MDW
17h 13m2 stops
 Logo
6:26 pm - 7:21 pmMDW-PIT
23h 55m1 stop
Sun, Oct 12 - Sun, Oct 19
Frontier Logo
5:40 pm - 12:36 amPIT-MDW
7h 56m1 stop
Frontier Logo
8:25 am - 1:41 pmMDW-PIT
4h 16m1 stop
$192Frontier
Find Deal
Fri, Oct 24 - Mon, Oct 27
Delta Logo
4:50 pm - 10:14 pmPIT-MDW
6h 24m1 stop
Delta Logo
1:08 pm - 6:54 pmMDW-PIT
4h 46m1 stop
$208Delta
Find Deal
Fri, Oct 17 - Mon, Oct 20
 Logo
9:26 pm - 10:21 amPIT-MDW
13h 55m1 stop
 Logo
5:28 pm - 10:21 amMDW-PIT
15h 53m1 stop

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
Arrive early at PIT due to construction delays.
Use the CTA Orange Line from MDW for quick downtown access.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Southwest
Cheapest • from $97 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
December
Cheapest • 25% price drop
September
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$97
Overall average: $266
Southwest
Tue 10/14Tue 10/21
PIT - MDW • Non-stop
Cheapest one-way
$49
Typical prices: $112-199
Southwest
Wed 10/15
PIT - MDW • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Expert advice

Expert advice for your flight from Pittsburgh to Midway

 
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
PIT

Arrive early at PIT due to ongoing construction and potentially busy security lines, especially for morning flights.

Read more about PITby Matt Meltzer
MDW

Use the CTA Orange Line from MDW for a quick, 25-30 minute ride to downtown Chicago, avoiding traffic delays.

Read more about MDWby Stefanie Waldek
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
Booking Insights

KAYAK's insights & trends for Pittsburgh to Midway flights

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 round-trip flights from Pittsburgh to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Pittsburgh to Chicago Midway Airport, look for departures on Wednesdays and avoid leaving on a Saturday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Wednesday is the cheapest day to fly and Sunday is the most expensive.

What is the cheapest month to fly from Pittsburgh to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Pittsburgh to Chicago Midway Airport, 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 Pittsburgh to Chicago Midway Airport is December, where tickets cost $236 (return) on average. On the other hand, the most expensive months are August and June, where the average cost of round-trip tickets is $435 and $372 respectively.

Can I save money by flying with a layover from Pittsburgh to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $255, prices are generally cheapest when you fly direct.

Good to know

Low seasonJuly
Cheapest flight$49
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly and prices are also 9% lower on average.
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 $49 for a one-way ticket and $97 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?

    American Airlines, Delta, Alaska Airlines, and JetBlue offer 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.

KAYAK’s top tips for finding a cheap flight from Pittsburgh to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $198 or less one-way and $250 or less round-trip.

Prefer to fly direct from Pittsburgh to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Pittsburgh to Chicago Midway.
Find which airlines fly direct from Pittsburgh Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct 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

Direct 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

Reviews of the 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
SouthwestOverall score based on 4242 reviews
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
8.1Boarding
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

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

Information on your arrival and departure airports

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